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Murphy's Landing Vacation House Rental: 102121

Murphy's Landing

Description: Welcome to Murphy's Landing which is a large home on a clear, flow through swimming canal. With 65 feet of seawall and 4.5 feet of… More

Bedrooms: 4
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

A Touch of Bermuda at Truman Annex Vacation Cottage Rental: 102572

A Touch of Bermuda at Truman Annex

Description: Envision yourself relaxing in a beautiful wood framed conch cottage with sloping tin roof in the heart of Old Town in Key West. This… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1700  to  2100 

*Rates Subject to Change

 

Canal Home Salt Marsh Sunset View Vacation House Rental: 102618

Canal Home Salt Marsh Sunset View

Description: Beautiful 3 bedroom, 2 bath canal front home with own dock & clean canal to swim in. Quick easy access to gulf or Atlantic. Dive… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 3200  to  3200 

*Rates Subject to Change

 

Henry's Piece Of Paradise On The Ocean In Key West (nightly / weekly) Vacation Condo Rental: 103905

Henry's Piece Of Paradise On The Ocean In Key West (nightly / weekly)

Description: 1350 sq ft of fabulous living space located on the 2nd floor, with garden and partial ocean views from a 38 ft private balcony… More

Bedrooms: 2
Sleeps: 4

*Rates: extra-night, From: 245  to  375 

*Rates Subject to Change

 

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals) Vacation Condo Rental: 112032

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)

Description: Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private… More

Bedrooms: 2
Sleeps: 6

*Rates: extra-night, From: 265  to  395 

*Rates Subject to Change

 

Large Private Home on Deep Canal w/ Ocean Access Vacation House Rental: 116177

Large Private Home on Deep Canal w/ Ocean Access

Description: Experience the uniqueness of the Lower Keys while staying in a spacious, three-bedroom private home on Big Pine Key, home to the… More

Bedrooms: 3
Sleeps: 9

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Truman Annex, Old Town, Key West, Private Setting with Luxury Features Vacation House Rental: 123714

Truman Annex, Old Town, Key West, Private Setting with Luxury Features

Description: Fully maintained and cared for, luxury features, just two blocks from Duval and Mallory Square in Old Town Key West, a two story… More

Bedrooms: 2
Sleeps: 5

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Hemingway Hideaway in the Heart of Key West--Tasteful, Charming Vacation House Rental: 127835

Hemingway Hideaway in the Heart of Key West--Tasteful, Charming

Description: Historic charmer, one block from Ernest Hemingway's home, great location, and off street parking for two cars. There is historic… More

Bedrooms: 3
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Charming waterfront home on private 2 acre lot with pool and dock. Vacation … Rental: 129524

Charming waterfront home on private 2 acre lot with pool and dock.

Description: Secluded, well-maintained tropical paradise, backs up to bay, has canal along one side, and wooded area along the other. Enchanting… More

Bedrooms: 3
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Key West Oceanfront Condo - 'The Sea Jay' Vacation Condo Rental: 134883

Key West Oceanfront Condo - 'The Sea Jay'

Description: The condo is quite large at over 1100 square feet and looks directly at beautiful Smathers Beach. The 'Sea Jay' is located in La… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval.. Vacation Cottage Rental: 135603

'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..

Description: 'Casa Louisa' is a cozy and charming turn-of-the-century cigar cottage located in the center of the historic cigar-making district… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekend, From: 400  to  665 

*Rates Subject to Change

 

Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio Vacation Townhome Rental: 135930

Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio

Description: 'The Plantation' is a 3 bed 3 bath townhome located within the gated community of Truman Annex in Key West's Old Town area. In… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2200  to  3200 

*Rates Subject to Change

 

Truman Annex: Flamingo Beach Self Catering Beautiful Ground flr condo w/lge deck Vacation Condo Rental: 136334

Truman Annex: Flamingo Beach Self Catering Beautiful Ground flr condo w/lge deck

Description: 'Flamingo Beach' is a beautiful ground floor condominium located within the prestigious gated community of 'Truman Annex' in Key… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1200  to  1800 

*Rates Subject to Change

 

St. Croix - Ramrod Key, Florida Vacation House Rental: 13719

St. Croix - Ramrod Key, Florida

Description: You'll enjoy this quiet, residential neighborhood as you relax on the back porch of this comfortable vacation home. 52 feet of boat… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2650  to  2650 

*Rates Subject to Change

 

Cudjoe Ocean Shores - Cudjoe Key, Florida Vacation House Rental: 13721

Cudjoe Ocean Shores - Cudjoe Key, Florida

Description: Enjoy the rustle of swaying palms and the balmy tropical breezes from the screened and tiled balcony of this immaculate Island home.… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2700  to  2900 

*Rates Subject to Change

 

Casa Rosado- Cudjoe Key, Florida Vacation House Rental: 13723

Casa Rosado- Cudjoe Key, Florida

Description: This beautiful, vacation home is tropical, bright and confortable. You'll wish it was your own! Tiki Hut and hammock dockside,… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4800  to  4800 

*Rates Subject to Change

 

Beautiful Cudjoe Gardens - Water Views From Every Room - Granite, Wi,fi, spa on Vacation House Rental: 140161

Beautiful Cudjoe Gardens - Water Views From Every Room - Granite, Wi,fi, spa on

Description: This new Cudjoe Gardens beauty has every upscale amenity for your tropical getaway. Located at the end of a quiet street on the… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Villa Soleil-Enjoy America's Caribbean with Style and Comfort Vacation Townhome Rental: 141421

Villa Soleil-Enjoy America's Caribbean with Style and Comfort

Description: Villa Soleil is an elegant townhouse located in the Truman Annex section of Old Town, close to the ocean and great sunset views.… More

Bedrooms: 2
Sleeps: 6

*Rates: extra-night, From: 229  to  315 

*Rates Subject to Change

 

A quiet, luxury condo close to the Ocean with nightly rates from $175-$225 Vacation Condo Rental: 145707

A quiet, luxury condo close to the Ocean with nightly rates from $175-$225

Description: This luxury condo is located at the Sunrise Suites Resort just a short walk across the road to the Ocean with a recreational path 2… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Truman Annex (Gated 4BR's/4Bath's-private Pool) Vacation House Rental: 146133

Truman Annex (Gated 4BR's/4Bath's-private Pool)

Description: Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block away from… More

Bedrooms: 4
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

The Beach House (Ocean Front) in Big Pine Key, FL-Amazing Ocean Views! Vacation House Rental: 147325

The Beach House (Ocean Front) in Big Pine Key, FL-Amazing Ocean Views!

Description: Fantastic Direct Beach Front House! If you are a nature lover, this is the house to rent in the Lower Keys. Long Beach Estates is an… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 6000  to  6000 

*Rates Subject to Change

 

Casa de Suenos (House of Dreams) Vacation Condo Rental: 147469

Casa de Suenos (House of Dreams)

Description: Delightful in every way describes this hidden gem located in the Meadows area of Old Town Key West. This is a one bedroom, one… More

Bedrooms: 1
Sleeps: 4

*Rates: monthly, From: 2500  to  4500 

*Rates Subject to Change

 

Captain Ron's Tropical Vacation Hide Away Vacation House Rental: 149014

Captain Ron's Tropical Vacation Hide Away

Description: On the Water Stilt home on boating canal 1/4 mile from the open water. Fully furnished, central air conditioned, decorated in… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2500  to  2500 

*Rates Subject to Change

 

DIRECT OCEANFRONT FREE WIFI & HBO Vacation Condo Rental: 149233

DIRECT OCEANFRONT FREE WIFI & HBO

Description: ! Nothing between our balcony and the ocean except 20 yards of sand! Free high speed wireless Internet! This very upscale unit is… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2400  to  3350 

*Rates Subject to Change

 

Beautiful Cudjoe Ocean Shores Waterfront Home - Fall Specials Available Vacation House Rental: 149850

Beautiful Cudjoe Ocean Shores Waterfront Home - Fall Specials Available

Description: We have everything you are looking for in a great Florida Keys vacation. Beautiful Cudjoe Key is just 23 miles from Historic Key… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 2800  to  3200 

*Rates Subject to Change

 

Blue water, dual canal front home! fishing, boating, lobstering and relaxing! Vacation House Rental: 150899

Blue water, dual canal front home! fishing, boating, lobstering and relaxing!

Description: Brand new, beautiful two bedroom, two bathroom, stilt waterfront home. Sleeps six. Screened entry leads to french doors. The master… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 900  to  900 

*Rates Subject to Change

 

Truman Annex - Renovated End Unit with Open Floorplan - Aug/Sept Special $99nt Vacation Condo Rental: 151840

Truman Annex - Renovated End Unit with Open Floorplan - Aug/Sept Special $99nt

Description: Brand new kitchen appliances, freshly painted, and hardwoods polished March 2010!!! Please read the reviews, we pride ourselves on… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Florida Keys Waterfront Cottage w/Pool and Ocean Views in Great Area Vacation Cottage Rental: 152144

Florida Keys Waterfront Cottage w/Pool and Ocean Views in Great Area

Description: Location, location, location! Cute cottage on the oceanside of the Florida Keys on a protected deep water canal one lot in from the… More

Bedrooms: 1
Sleeps: 4

*Rates: extra-night, From: 110  to  110 

*Rates Subject to Change

 

Luxury historic home near Duval Street available for monthly rental Vacation House Rental: 153705

Luxury historic home near Duval Street available for monthly rental

Description: This 3 bedroom, 3 1/2 bathroom Old Town historic home has been totally remodeled to an exceptionally high standard and offers… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3500  to  7700 

*Rates Subject to Change

 

Oceanfront Condominium - Direct Oceanfront at the Coral Reef Vacation Condo Rental: 154612

Oceanfront Condominium - Direct Oceanfront at the Coral Reef

Description: You feel it the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm set into motion over a… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 250  to  390 

*Rates Subject to Change

 

3 story home off the Canal, boat dock, pool, jacuzzi, breathtaking sunsets! Vacation House Rental: 155204

3 story home off the Canal, boat dock, pool, jacuzzi, breathtaking sunsets!

Description: Keyora..a Jewel in the crown of Summerland Cove Isle. Located in a quiet, serene neighborhood. You are spoilt for view ..open water,… More

Bedrooms: 4
Sleeps: 10

*Rates: monthly, From: 6500  to  6500 

*Rates Subject to Change

 

Beautiful spacious home with heated pool and spectacular ocean views! Vacation House Rental: 155730

Beautiful spacious home with heated pool and spectacular ocean views!

Description: This beautiful, tastefully furnished home is located on the open water of the Atlantic Ocean and has all the amenities of home. With… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Beautiful Oceanfront Home With Heated Pool Vacation House Rental: 156413

Beautiful Oceanfront Home With Heated Pool

Description: Sit back and relax in this delightful home on the open water. Equipped with all the comforts of home plus a heated pool and wifi… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3000  to  5200 

*Rates Subject to Change

 

Truman Annex 2bed/1bath condo, premier downtown Key West location and amenities Vacation Condo Rental: 156587

Truman Annex 2bed/1bath condo, premier downtown Key West location and amenities

Description: Our 2bed/1 bath condo in the lovely gated community of Truman Annex provides the perfect way to experience Key West- like a local.… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1050  to  1900 

*Rates Subject to Change

 

Beautiful Duval St. Condo, Location, Location!!!! Vacation Condo Rental: 156723

Beautiful Duval St. Condo, Location, Location!!!!

Description: Location, Location, Location!!! You can't find a better location than Duval St. One of only three unique units. This Condo is above… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekend, From: 200  to  275 

*Rates Subject to Change

 

Serendipity, Serenity and Simplicity--Call and ask about our specials now Vacation Cottage Rental: 158112

Serendipity, Serenity and Simplicity--Call and ask about our specials now

Description: Please Call Marilyn at 614-746-4702 from 9:00am to 10:00pm eastern std time. You will love staying in this great location where 90%… More

Bedrooms: 1
Sleeps: 3

*Rates: weekly, From: 925  to  1595 

*Rates Subject to Change

 

Villa Nomade, Elegant Truman Annex condo in Old Town Vacation Condo Rental: 158403

Villa Nomade, Elegant Truman Annex condo in Old Town

Description: Villa Nomade is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1200  to  2000 

*Rates Subject to Change

 

High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Rentals Only Vacation House Rental: 159918

High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Rentals Only

Description: (Monthly Rentals Only) : 621 Canfield Lane, Key West, Florida Tucked away at the end of a quiet and peaceful Old Town Lane is this… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Open Water Home with Pool, Boat Lift and Tiki Hut Vacation House Rental: 160456

Open Water Home with Pool, Boat Lift and Tiki Hut

Description: Private, tropical, open water home offers everything you want for your true Keys vacation. Keep your boat on the 12,000 lb lift.… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 8000  to  8000 

*Rates Subject to Change

 

Luxury Waterfront at the Galleon Resort in Old Town Vacation Condo Rental: 161268

Luxury Waterfront at the Galleon Resort in Old Town

Description: This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, fully equipped… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekend, From: 400  to  585 

*Rates Subject to Change

 

FALL DISCOUNTS- 6/4 Huge home/Private dock/ Pool/ Ice maker/ Fishing Vacation House Rental: 162258

FALL DISCOUNTS- 6/4 Huge home/Private dock/ Pool/ Ice maker/ Fishing

Description: You’ll love this house! It has 6 Bedrooms 4 baths, can accommodate up to 18 people in beds. Thirty foot solar heated pool surrounded… More

Bedrooms: 6
Sleeps: 18

*Rates: monthly, From: 7950  to  7950 

*Rates Subject to Change

 

Oceanfront Vacation Condo Rental: 162417

Oceanfront

Description: Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront condominium… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Fully Equipped Condo in the Heart of Beautiful Key West Vacation Condo Rental: 162533

Fully Equipped Condo in the Heart of Beautiful Key West

Description: Come and enjoy our newly furnished ground level condo. We are located in historic Truman Annex, centrally located in Old Town Key… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Sunset Shores - Endless panoramic bay views! Vacation House Rental: 163013

Sunset Shores - Endless panoramic bay views!

Description: Experience breathtaking sunsets and escape to your own private corner of paradise at Sunset Shores. This Caribbean style 3 bedroom,… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Gorgeous Waterfront Condominium With Stunning Views! Vacation Condo Rental: 163420

Gorgeous Waterfront Condominium With Stunning Views!

Description: Luxurious! Comfortable! Unforgettable! Located on the Atlantic Ocean with magnificent views, this beautifully decorated tropical… More

Bedrooms: 2
Sleeps: 4

*Rates: extra-night, From: 300  to  335 

*Rates Subject to Change

 

Annex Luxury - Location and Classic Key West Charm Vacation House Rental: 164696

Annex Luxury - Location and Classic Key West Charm

Description: Classic Key West charm and great location within the Truman Annex gated community make this home of distinction an ideal place for… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 1989  to  3849 

*Rates Subject to Change

 

Key West - Poolside Conch Paradise at Key West Golf Club Vacation Townhome Rental: 164920

Key West - Poolside Conch Paradise at Key West Golf Club

Description: This cute and airy, 2 bedroom bungalow style home, has been tastefully decorated and freshly painted to make your stay comfortable… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Waterfront Luxury in Old Town Key West Vacation Condo Rental: 166032

Waterfront Luxury in Old Town Key West

Description: This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a… More

Bedrooms: 1
Sleeps: 5

*Rates: nightly-weekend, From: 280  to  420 

*Rates Subject to Change

 

Sophisticated Elegance on Fleming Street Vacation House Rental: 166595

Sophisticated Elegance on Fleming Street

Description: Constructed in 1859, this prestigious Key West home exemplifies elegant tropical living. Superb renovations in 2006-07 perfect the… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 8000  to  13000 

*Rates Subject to Change

 

Campbell Courtyard Townhouse 'In the Sky' Vacation Townhome Rental: 167721

Campbell Courtyard Townhouse 'In the Sky'

Description: Few properties in Key West can offer a true combination of quality, location and privacy like this one! Perched above the 600-block… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3500  to  5500 

*Rates Subject to Change

 

Charming and Private Vacation House Rental: 169213

Charming and Private

Description: 20 Miles from Key West and mini golf, private pool & hot tub, deluxe outdoor kitchen, outdoor shower, screened in porch all around,… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

HISTORIC RESTORED 'EYEBROW' HOME SPRING/SUMMER SPECIALS!!!!! Vacation House Rental: 169698

HISTORIC RESTORED 'EYEBROW' HOME SPRING/SUMMER SPECIALS!!!!!

Description: One month minimum rental!! This Historic home was built in 1895 and lovingly restored in 2001.This is one of only two eyebrow style… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5500  to  7500 

*Rates Subject to Change

 

Charming and affordable Florida Keys rental Vacation House Rental: 172080

Charming and affordable Florida Keys rental

Description: Away from it all 'Little Torch Key home' just 30 minutes from Key West night life and entertainment, and 9 miles from Bahia Honda… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 1850  to  1850 

*Rates Subject to Change

 

William Skelton -- Location, Location, Location! in Old Town Key West Vacation House Rental: 172563

William Skelton -- Location, Location, Location! in Old Town Key West

Description: A hidden gem in Old Town!! It can be rented as a 4 bedroom/3 bath or as a 6 bedroom/4 bath. Our flexibility allows you more… More

Bedrooms: 6
Sleeps: 16

*Rates: nightly-weekend, From: 480  to  480 

*Rates Subject to Change

 

Waterfront Ocean Views, Deep Clear Canal, Spacious New Home Vacation House Rental: 172703

Waterfront Ocean Views, Deep Clear Canal, Spacious New Home

Description: Our exclusive private waterfront home has fantastic water views in every room of this 3 level home. Located on the Ocean-side. The 3… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Private Estate: A Peaceful Oasis Vacation Estate Rental: 173113

Private Estate: A Peaceful Oasis

Description: Description: Traditional yet stylish with careful attention to classic detail. Timeless elements throughout including 10ft ceilings… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 12500  to  12500 

*Rates Subject to Change

 

Kings Pointe Oceanside Luxury 3 Bedroom Condo Vacation Condo Rental: 173862

Kings Pointe Oceanside Luxury 3 Bedroom Condo

Description: Kings Pointe Marina Formerly Oceanside Marina Condos are located directly on the ocean, with 22 recently constructed condominiums… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

OceanFront Home w/Heated Pool, Dock, WiFi - pet friendly - March '12 available Vacation House Rental: 174010

OceanFront Home w/Heated Pool, Dock, WiFi - pet friendly - March '12 available

Description: Breezeswept Villa is just three years old and is located on the open water in a tropical coastal community of waterfront homes on… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 2750  to  7350 

*Rates Subject to Change

 

Spectacular Open Water Views in The Lower Keys Vacation House Rental: 174264

Spectacular Open Water Views in The Lower Keys

Description: We chose this home specifically for its location, it is on the open water with a canal. It has immense Open Water views in a… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1000  to  1000 

*Rates Subject to Change

 

Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach Vacation Condo Rental: 174733

Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach

Description: Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2 bedrooms, 2 full bathrooms, sleeps 6, wireless internet access More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

On Smather's Beach - Key West Ocean Side Luxury w/ High Speed Internet Vacation Condo Rental: 174861

On Smather's Beach - Key West Ocean Side Luxury w/ High Speed Internet

Description: Be our guest at one of the best that 1800 Atlantic Condominiums has to offer. With a wonderful tropical setting on the Atlantic… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4400  to  4900 

*Rates Subject to Change

 

Historical Conch Home with Pool Vacation House Rental: 175555

Historical Conch Home with Pool

Description: This conch single family home (listed on the National Historic Register) located in the heart of Key West's “Old Town District” is… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Little Torch Key Tropical Paradise Vacation House Rental: 176318

Little Torch Key Tropical Paradise

Description: Little Torch Key, Oceanside at mile marker 28 feels like paradise. This truly unique, delightful tropical paradise is only a 25… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3500  to  3750 

*Rates Subject to Change

 

Gated Private Luxurious Getaway-Truman Annex (Private Pool) Vacation House Rental: 177296

Gated Private Luxurious Getaway-Truman Annex (Private Pool)

Description: Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block from Duval… More

Bedrooms: 3
Sleeps: 7

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Another Day In Paradise Vacation House Rental: 177620

Another Day In Paradise

Description: Very nice, 3 story clear canal front home with breathtaking sunset views overlooking the bird sanctuary ! Unforgettable open water… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Escape From It All at the 'Great Escape'! Vacation House Rental: 177849

Escape From It All at the 'Great Escape'!

Description: Welcome to the Great Escape! Get away from it all, and yet, be in the midst of it all, in a location that offers everything needed… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Monthly Rates-KW living at its finest-quiet neighborhood, near duval and beach Vacation House Rental: 180167

Monthly Rates-KW living at its finest-quiet neighborhood, near duval and beach

Description: Well maintained recently renovated luxury home with heated pool in very private yard. This charming home was built in 1918 so it has… More

Bedrooms: 3
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Casita Marina- sunsets in backyard over clear blue ocean Vacation House Rental: 181611

Casita Marina- sunsets in backyard over clear blue ocean

Description: Our newly renovated 4100+ square foot house has 6 bedrooms 4.5 bathrooms houses situated on open water on Summerland Key. This… More

Bedrooms: 6
Sleeps: 12

*Rates: monthly, From: 18000  to  18000 

*Rates Subject to Change

 

Key West Rental (Casa De Suenos) House of Dreams! Vacation Condo Rental: 182589

Key West Rental (Casa De Suenos) House of Dreams!

Description: Casa de Suenos, an English Dream house that is Delightful in every way. This hidden gem was completely re-done as a custom upscale… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Private and Peaceful Cottage feeling, With a 7 night stay you get 1 night FREE! Vacation House Rental: 184497

Private and Peaceful Cottage feeling, With a 7 night stay you get 1 night FREE!

Description: You will love staying in this great location where 90% of the residents are local. They each have an interesting Key West tale to… More

Bedrooms: 1
Sleeps: 3

*Rates: nightly-weekend, From: 135  to  135 

*Rates Subject to Change

 

'ISLAND IN THE STREAM' - Spacious Waterfront Home with Access to Ocean & Bay Vacation House Rental: 184573

'ISLAND IN THE STREAM' - Spacious Waterfront Home with Access to Ocean & Bay

Description: ONE OF THE BEST LOCATIONS IN THE FLORIDA KEYS! Close to US 1, and Pine Channel which gives boaters immediate access to both the… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3450  to  3450 

*Rates Subject to Change

 

Bargain Rates in Truman Annex - Heart of Old Town, Key West Vacation Condo Rental: 184913

Bargain Rates in Truman Annex - Heart of Old Town, Key West

Description: This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorated. Fresh… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 995  to  1695 

*Rates Subject to Change

 

The Perfect Get-away in Paradise Vacation Condo Rental: 185263

The Perfect Get-away in Paradise

Description: The Galleria Condominiums, a wonderful, quiet retreat for a fun-filled and relaxing get-away! Each efficiency condo bears the name… More

Bedrooms: 0
Sleeps: 4

*Rates: nightly-weekend, From: 105  to  119 

*Rates Subject to Change

 

Fretz House (Big Torch Key) Open Waterfront Home w/Deep Water Dock, Sunset views Vacation House Rental: 187305

Fretz House (Big Torch Key) Open Waterfront Home w/Deep Water Dock, Sunset views

Description: - WEEKLY RENTALS!!!! - Vacationing in the Florida Keys is often referred to as one of the most memorable times you will ever… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1500  to  1500 

*Rates Subject to Change

 

Spectacular,1from OPEN water,Best Fish,Dive,Snorkel,Views! Vacation House Rental: 187539

Spectacular,1from OPEN water,Best Fish,Dive,Snorkel,Views!

Description: Beautifully renovated in/out large home. One in from Open water on canal, awesome views, unique cut in boat SLIP under the house!… More

Bedrooms: 3
Sleeps: 7

*Rates: monthly, From: 4750  to  4750 

*Rates Subject to Change

 

Private Key West Weekly Vacation rental in the heart of Old Town Vacation House Rental: 187859

Private Key West Weekly Vacation rental in the heart of Old Town

Description: The Pineapple Cottage is a weekly vacation rental that offers what everyone wants: A great location and total privacy! Surrounded by… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1900  to  2800 

*Rates Subject to Change

 

Heron Estate -- Luxury Rental on water with dock. Now booking New Year's week! Vacation Estate Rental: 188043

Heron Estate -- Luxury Rental on water with dock. Now booking New Year's week!

Description: A large four bedroom / 4 bath estate with dock is located on Key West’s only canal, making this the perfect home for boaters and… More

Bedrooms: 4
Sleeps: 9

*Rates: monthly, From: 7000  to  8000 

*Rates Subject to Change

 

Truman Annex: Paradise Lost Self Catering Unique ground floor condominium Vacation Condo Rental: 188482

Truman Annex: Paradise Lost Self Catering Unique ground floor condominium

Description: Paradise Lost' is a unique two bedroom, two bath, ground floor condominium located within the prestigious gated community of 'Truman… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1400  to  2000 

*Rates Subject to Change

 

Villa Soleil, Elegant Truman Annex condo in Old Town Key West Vacation Condo Rental: 188516

Villa Soleil, Elegant Truman Annex condo in Old Town Key West

Description: Villa Soleil is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1200  to  2000 

*Rates Subject to Change

 

Beautiful Retreat in Key West Area Vacation House Rental: 188664

Beautiful Retreat in Key West Area

Description: Our beautiful home is located on the bayside in Big Coppitt Key. Wake up in the morning to stunning views of the bay. The house is… More

Bedrooms: 5
Sleeps: 12

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Waterfront Pool Home w/ Hot tub & Tiki Hut- Private Boat Dock Vacation House Rental: 192107

Waterfront Pool Home w/ Hot tub & Tiki Hut- Private Boat Dock

Description: The Cabana del Sol is ½ acre spacious property with swimming pool & hot tub with sun deck on 150ft of waterfront property. Cute and… More

Bedrooms: 4
Sleeps: 12

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Cudjoe Key--VENTURE OUT - Tropical Paradise Gated Resort, Key West 19 Miles Vacation Cottage Rental: 193289

Cudjoe Key--VENTURE OUT - Tropical Paradise Gated Resort, Key West 19 Miles

Description: For a TROPICAL VACATION come to our beautiful designer furnished cottage/mobile home at Venture Out Resort on Cudjoe Key. We pride… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 120  to  130 

*Rates Subject to Change

 

Oceanfront Seclusion Vacation Villa Rental: 194747

Oceanfront Seclusion

Description: Located on the open water on the south side of Cudjoe Key, this home is that special place where you can get away from it all.… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Great Key West Rental Vacation House Rental: 195229

Great Key West Rental

Description: This three bedroom home boasts of many special features and offers a perfect location. The upstairs can sleep 6-8 . Laying at the… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Hemingway's Hideaway Truman Annex Vacation Townhome Rental: 195479

Hemingway's Hideaway Truman Annex

Description: Location, Location, Location, Best in Truman Annex, private yet has front deck plus deck off main bedroom. Near all major… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1825  to  1825 

*Rates Subject to Change

 

Barry Beach Vacation House Rental: 19757

Barry Beach

Description: Enjoy the ultimate in relaxation at this Gulf side home in Little Torch Key. This tropical hideaway is located on the open water… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2850  to  3000 

*Rates Subject to Change

 

Bay Pointe Vacation House Rental: 19759

Bay Pointe

Description: Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental has 2 large screen porches… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 3800  to  4200 

*Rates Subject to Change

 

Breeze Swept Vacation House Rental: 19760

Breeze Swept

Description: Magnificent open water views in this beautiful 3 Bedrooms 2 bath home on Big Pine Key. This home boasts décor by award winning Key… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5600  to  5900 

*Rates Subject to Change

 

Caribbean Dream Vacation House Rental: 19761

Caribbean Dream

Description: This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. We added… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 5500  to  6000 

*Rates Subject to Change

 

Casa del Sol Vacation House Rental: 19762

Casa del Sol

Description: Sit back and relax in this delightful home, situated on the open water. Equipped with all the comforts of home plus a heated pool.… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5000  to  5200 

*Rates Subject to Change

 

Cove Isles Vacation House Rental: 19765

Cove Isles

Description: This contemporary vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2800  to  3100 

*Rates Subject to Change

 

Dolphin Point Vacation House Rental: 19769

Dolphin Point

Description: You’ll never forget your Florida Keys vacation after spending some time at this magnificent home. Located in Cudjoe Gardens which… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3900  to  4300 

*Rates Subject to Change

 

Egret's Landing Vacation House Rental: 19770

Egret's Landing

Description: From the private balcony located off the master bedroom living area, to airy and vaulted ceilings, this Cape Cod style home promises… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2900  to  3400 

*Rates Subject to Change

 

Flying Cloud Vacation House Rental: 19771

Flying Cloud

Description: Fishing. Swimming. Boating.... Whatever your pleasure, the protective 75' seawall and clear, clean deepwater boating canal offers… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2750  to  2750 

*Rates Subject to Change

 

Gulf Shores Vacation House Rental: 19772

Gulf Shores

Description: Sit back and relax in this clean, airy, and spacious vacation home. Located on a canal and equipped with all the conforts of home.… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2750  to  2750 

*Rates Subject to Change

 

Hammerhead Retreat Vacation House Rental: 19773

Hammerhead Retreat

Description: Bordered by the crystal-blue waters of the Atlantic Ocean, this fenced, open-water property comes equipped with all the… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 3900  to  3900 

*Rates Subject to Change

 

Heron's Roost Vacation House Rental: 19774

Heron's Roost

Description: Come and enjoy the easy life when you select this wonderful vacation home in Doctor's Arm on Big Pine Key. This home has 3 Bedrooms… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3750  to  3900 

*Rates Subject to Change

 

Lazy Lagoon Vacation House Rental: 19775

Lazy Lagoon

Description: Looking for that perfect vacation spot in the Keys? This is the one. Luxury waterfront accommodations await for the whole group.… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5600  to  5900 

*Rates Subject to Change

 

Mango House Vacation House Rental: 19776

Mango House

Description: Simple and sweet with no muss, no fuss. It's all right here - Gulf Side! This quaint two bedroom vacation home offers views, a… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 1800  to  2300 

*Rates Subject to Change

 

Paradise Bay Vacation House Rental: 19780

Paradise Bay

Description: This great Vacation Home is conveniently located on Cudjoe Key. The all tile kitchen is fully equipped and living & dining rooms… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2750  to  3100 

*Rates Subject to Change

 

Pirate's Cove Vacation House Rental: 19781

Pirate's Cove

Description: Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2000  to  2200 

*Rates Subject to Change

 

Summer Isle Vacation House Rental: 19787

Summer Isle

Description: Surrounded by lush, tropical landscaping, this gated open-water vacation home comes equipped will all the thoughtful touches of home… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 6900  to  7200 

*Rates Subject to Change

 

Suncatcher's Dream Vacation House Rental: 19788

Suncatcher's Dream

Description: Cudjoe Key Pool Home!!!! Relax and enjoy this light and tropical, like-new vacation home. Step onto the large open porch and soak in… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4500  to  4800 

*Rates Subject to Change

 

Truman Annex - Foundry Townhouse - One of a Kind! Vacation Townhome Rental: 200634

Truman Annex - Foundry Townhouse - One of a Kind!

Description: Once you see this roomy two storey townhouse, you won’t want to stay anywhere else! Filled with natural light, this end unit is… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 2000  to  2150 

*Rates Subject to Change

 

Contemporary Condo at Truman Annex-Walk to Beach/Duval St. Vacation Condo Rental: 203228

Contemporary Condo at Truman Annex-Walk to Beach/Duval St.

Description: Decorated in casual contemporary style, our second floor condo is newly-renovated, and centrally located in the Truman Annex, within… More

Bedrooms: 2
Sleeps: 5

*Rates: weekly, From: 1200  to  1400 

*Rates Subject to Change

 

Beautiful Canal Home with a Pool, Spa and Boat Lift Vacation House Rental: 203289

Beautiful Canal Home with a Pool, Spa and Boat Lift

Description: Located in a great neighborhood at 1032 Spanish Main, this home is perfect for your next vacation. This very clean and neat 3… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 1300  to  1300 

*Rates Subject to Change

 

Mermaid's Rock Vacation House Rental: 203762

Mermaid's Rock

Description: Mermaid's Rock is located in prestigious Truman Annex, only 1 block from Duval Street and the famous Mallory Square sunset. No car… More

Bedrooms: 4
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Truman Annex: Southern Palm Self Catering Spacious town home with large deck Vacation Townhome Rental: 204471

Truman Annex: Southern Palm Self Catering Spacious town home with large deck

Description: Southern Palm is a townhome located within the gated community of Truman Annex in Key West's Old Town area. The Master Bedroom has… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 5400  to  7800 

*Rates Subject to Change

 

Key West's Sunset Marina Ocean Front Condo Vacation Condo Rental: 204628

Key West's Sunset Marina Ocean Front Condo

Description: Everything you will need to assure your Key West Vacation is a success is here at my Sunset Marina Ocean Front Condo. The best… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Amazing open water view with quick easy access to ocean and gulf Vacation House Rental: 204964

Amazing open water view with quick easy access to ocean and gulf

Description: Spacious 3 bedroom waterfront home with open wrap around deck. Private balcony off master bedroom provides spectacular open water… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Villa Fleur, Elegant Truman Annex condo in Old Town Vacation Condo Rental: 207098

Villa Fleur, Elegant Truman Annex condo in Old Town

Description: Villa Fleur is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1200  to  1500 

*Rates Subject to Change

 

Tropical Reatreat! Vacation House Rental: 207517

Tropical Reatreat!

Description: Came and stay for month or more in our charming hideaway while you experience the magic of Key West. We make your vacation memorable… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 5500  to  8000 

*Rates Subject to Change

 

Key West 3 Bedroom Condo- Direct Beach Front Vacation Condo Rental: 208046

Key West 3 Bedroom Condo- Direct Beach Front

Description: Our 1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms and living room. There's a feeling of… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Atlantic Seclusion is very private with lush landscaping. Vacation House Rental: 208056

Atlantic Seclusion is very private with lush landscaping.

Description: Beautiful 3 bedroom 2 bath Caribbean-style waterfront home in Sugarloaf Shores. Complete privacy with lush landscaped grounds and… More

Bedrooms: 3
Sleeps: 7

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Secluded Keys Waterfront Getaway-Dock-Kayaks-Sun Deck Vacation House Rental: 208132

Secluded Keys Waterfront Getaway-Dock-Kayaks-Sun Deck

Description: Relax in this peaceful Keys getaway tucked away in beautiful Big Pine Key. From your sun deck you can observe abundant marine life,… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2690  to  3990 

*Rates Subject to Change

 

Paradise Manor with private pool available July and August 2011 Vacation House Rental: 208558

Paradise Manor with private pool available July and August 2011

Description: Beautiful and spacious house with private pool in quiet neighborhood. The house has a living room with TV, DVD, VCR, CD/radio,… More

Bedrooms: 4
Sleeps: 9

*Rates: monthly, From: 2990  to  4990 

*Rates Subject to Change

 

Key West Luxury 2 Bedroom Condo in The Shipyard of Truman Annex in Old Town Vacation Condo Rental: 208697

Key West Luxury 2 Bedroom Condo in The Shipyard of Truman Annex in Old Town

Description: Truman Annex is the most exclusive and magnificent development in Old Town, Key West with wide streets lined with multi-million… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Villa Paradiso Vacation House Rental: 20874

Villa Paradiso

Description: This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 360  to  730 

*Rates Subject to Change

 

Havana Lane Vacation House Rental: 20875

Havana Lane

Description: Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 310  to  530 

*Rates Subject to Change

 

Bali Hideaway Vacation House Rental: 20876

Bali Hideaway

Description: Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound just one half… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 180  to  281 

*Rates Subject to Change

 

Ann Street Tranquility Vacation Condo Rental: 20877

Ann Street Tranquility

Description: This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 200  to  330 

*Rates Subject to Change

 

Ann Street Cottage Vacation Condo Rental: 20878

Ann Street Cottage

Description: This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 160  to  280 

*Rates Subject to Change

 

Whitehead House Vacation House Rental: 20879

Whitehead House

Description: Unique two story, three bedroom, two bathroom home nested beside the Audubon House in Old Town Key West. Hidden behind the most… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 330  to  570 

*Rates Subject to Change

 

Key Lime Calypso Vacation House Rental: 20880

Key Lime Calypso

Description: The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 270  to  400 

*Rates Subject to Change

 

Pete's West Cottage Vacation House Rental: 20882

Pete's West Cottage

Description: This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 250  to  400 

*Rates Subject to Change

 

Pete's East Cottage Vacation House Rental: 20883

Pete's East Cottage

Description: This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 250  to  400 

*Rates Subject to Change

 

Casa de Cuba Vacation House Rental: 20884

Casa de Cuba

Description: Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 450  to  790 

*Rates Subject to Change

 

Louisa House Vacation House Rental: 20885

Louisa House

Description: Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost… More

Bedrooms: 4
Sleeps: 8

*Rates: nightly-weekday, From: 550  to  800 

*Rates Subject to Change

 

Coconut Cabana Vacation House Rental: 20886

Coconut Cabana

Description: An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 340  to  610 

*Rates Subject to Change

 

Duval Roost Vacation House Rental: 20887

Duval Roost

Description: This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a private lane. Enter the… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 390  to  700 

*Rates Subject to Change

 

Southard Street - Queen Conch Vacation House Rental: 20888

Southard Street - Queen Conch

Description: On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three… More

Bedrooms: 4
Sleeps: 8

*Rates: nightly-weekday, From: 700  to  1050 

*Rates Subject to Change

 

Vista Verde Vacation Condo Rental: 20889

Vista Verde

Description: Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 190  to  380 

*Rates Subject to Change

 

Beach Club #103 Vacation Condo Rental: 20891

Beach Club #103

Description: Unique oceanfront living sitting 65 feet from the Atlantic. Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 330  to  480 

*Rates Subject to Change

 

Beach Club #108 Vacation Condo Rental: 20892

Beach Club #108

Description: Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This elegant 3 bedroom/ 2… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2380  to  3710 

*Rates Subject to Change

 

Beach Club #201 Vacation Condo Rental: 20893

Beach Club #201

Description: Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 330  to  480 

*Rates Subject to Change

 

Beach Club #303 Vacation Condo Rental: 20894

Beach Club #303

Description: Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 330  to  480 

*Rates Subject to Change

 

Casa Atlantica One Bedroom Vacation Condo Rental: 20895

Casa Atlantica One Bedroom

Description: Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 170  to  260 

*Rates Subject to Change

 

Casa Atlantica Studio Vacation House Rental: 20896

Casa Atlantica Studio

Description: A spacious studio apartment and large deck make this the perfect romantic getaway, feast your eyes on the breathtaking views of the… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 160  to  250 

*Rates Subject to Change

 

Duval Square Penthouse Vacation House Rental: 20897

Duval Square Penthouse

Description: Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the… More

Bedrooms: 4
Sleeps: 8

*Rates: nightly-weekday, From: 410  to  720 

*Rates Subject to Change

 

Duval Square Courtyard Condo Vacation Condo Rental: 20899

Duval Square Courtyard Condo

Description: In the heart of Old Town, convenient to everything. The condo is set above a brick, tree lined courtyard that includes shops and… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 310  to  490 

*Rates Subject to Change

 

La Brisa #302E Tropical Tranquility Vacation Condo Rental: 20901

La Brisa #302E Tropical Tranquility

Description: La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 150  to  260 

*Rates Subject to Change

 

La Brisa #403E Ocean Vista Vacation Condo Rental: 20902

La Brisa #403E Ocean Vista

Description: La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 220  to  370 

*Rates Subject to Change

 

La Brisa #405E Sea Orchid Vacation Condo Rental: 20903

La Brisa #405E Sea Orchid

Description: La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  370 

*Rates Subject to Change

 

Key West vacation townhouse rental in the Truman Annex Vacation Townhome Rental: 209088

Key West vacation townhouse rental in the Truman Annex

Description: Attractive tropical conch style 2 story Presidents Walk townhouse on Southard St within the prestigious Truman Annex in Old Town.… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1000  to  2500 

*Rates Subject to Change

 

Key West ocean view luxury 3 bedroom Truman Annex vacation condo Vacation Condo Rental: 209190

Key West ocean view luxury 3 bedroom Truman Annex vacation condo

Description: Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This beautiful luxurious Harbor Place ocean… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 10000  to  17000 

*Rates Subject to Change

 

Petronia Palms, Just Off Duval St. and Has a Large Pool! Vacation Cottage Rental: 210550

Petronia Palms, Just Off Duval St. and Has a Large Pool!

Description: Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple Properties in Key West. Petronia Palms Is located just… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Living on Key West Time Vacation House Rental: 211102

Living on Key West Time

Description: Located on an excellent deep draft canal, fantastic boating with cool breezes. This new 3 bedroom 2 bath home includes all the… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2500  to  2500 

*Rates Subject to Change

 

Truman Annex - Two-Story Shipyard Cottage Vacation Condo Rental: 212151

Truman Annex - Two-Story Shipyard Cottage

Description: Our recently updated condominium is decorated in a tropical theme with all the amenities of home. The master bedroom has a king-size… More

Bedrooms: 2
Sleeps: 5

*Rates: weekly, From: 1300  to  1600 

*Rates Subject to Change

 

STILL A FEW FEB WEEKS,,,CK TODAY !!!! Vacation Townhome Rental: 212518

STILL A FEW FEB WEEKS,,,CK TODAY !!!!

Description: This end unit townhome features 2 bedroom, 1 and ½ bath and is located on President's walk in the prettiest section of the Truman… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Enjoy open water views & excellent fishing & snorkeling right from your backyard Vacation House Rental: 213724

Enjoy open water views & excellent fishing & snorkeling right from your backyard

Description: Best location in the lower keys - Everything you need to enjoy a perfect keys vacation: superb boating location, 60 foot concrete… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Spectacular Waterfront Paradise Vacation House Rental: 214002

Spectacular Waterfront Paradise

Description: Resort-like living - monthly or seasonal vacations in beautiful Lower Sugarloaf Key - just 15 minutes from Key West. All of our… More

Bedrooms: 5
Sleeps: 12

*Rates: monthly, From: 15545.18  to  15545.18 

*Rates Subject to Change

 

Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex Vacation Townhome Rental: 220630

Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex

Description: Enjoy all the charm Key West has to offer in this beautiful, newly renovated 4 bedroom/3 full bath house with private heated pool in… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 8100  to  14700 

*Rates Subject to Change

 

Relaxing, quiet, get-away just blocks from downtown Key West & Beach - MONTHLY Vacation House Rental: 223317

Relaxing, quiet, get-away just blocks from downtown Key West & Beach - MONTHLY

Description: This newly renovated home is perfect for a family or group of friends who want to get away and become 'temporary residents' of the… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 2700  to  6500 

*Rates Subject to Change

 

Luxury Key West Condo -All New Plus So Much More---- 8 Bikes Included Free! Vacation Condo Rental: 223545

Luxury Key West Condo -All New Plus So Much More---- 8 Bikes Included Free!

Description: Condo located less than 1/2 mile outside of Key West in new gated community in Stock Island. 1100 sq. ft, beautifully decorated in… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 200  to  450 

*Rates Subject to Change

 

*Available May* Charming Cudjoe Gardens Home Vacation House Rental: 223914

*Available May* Charming Cudjoe Gardens Home

Description: Welcome to Paradise! Your vacation officially begins as soon as you walk through the door of our lovely house. We have created a… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Sunset Villa with gorgeous Open Water views and sunsets Vacation House Rental: 224210

Sunset Villa with gorgeous Open Water views and sunsets

Description: Why stay at a hotel when you can enjoy beautiful open water views with extreme quiet and peacefulness at this end-of-the-road home.… More

Bedrooms: 3
Sleeps: 10

*Rates: monthly, From: 3200  to  3500 

*Rates Subject to Change

 

2010 Special Pricing Hemingway Style Cottage/Tropical Pool Vacation Cottage Rental: 224554

2010 Special Pricing Hemingway Style Cottage/Tropical Pool

Description: Just pack your shorts and sandals, your Jimmy Buffet CD's, pick up a Hemmingway book, and head for this fantastic 3 bedroom, 2… More

Bedrooms: 3
Sleeps: 8

*Rates: extra-night, From: 310  to  350 

*Rates Subject to Change

 

Oceanfront Sandy Beach & Dock Vacation House Rental: 224597

Oceanfront Sandy Beach & Dock

Description: Charming, oceanfront house directly on beach. Most beautiful spot in the Keys! Very private, like being on your own tropical island.… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 9500  to  11500 

*Rates Subject to Change

 

Petronia Palms, Just Off Duval St. and Has a Large Pool! Vacation Cottage Rental: 224674

Petronia Palms, Just Off Duval St. and Has a Large Pool!

Description: Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple rentals. Petronia Palms Is located just one block from… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

6 bedroom Compound w/ Pool, Hot Tub, Parking & Huge Roof Deck on Duval Street Vacation Villa Rental: 228157

6 bedroom Compound w/ Pool, Hot Tub, Parking & Huge Roof Deck on Duval Street

Description: Perfect location and great for entertaining! In the heart of Old Town Key West across from Margaritaville and just steps from… More

Bedrooms: 6
Sleeps: 14

*Rates: weekly, From: 7995  to  7995 

*Rates Subject to Change

 

Harbor Inn Condominium, Charming, quiet, elegant, beautiful, modern, luxury Vacation Condo Rental: 228335

Harbor Inn Condominium, Charming, quiet, elegant, beautiful, modern, luxury

Description: A beautiful, charming two bedroom, two bath condominium in an historic Key West home. No non-descript apartment building here. This… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Charming canal front home with great boating, lobstering, fishing Vacation House Rental: 229081

Charming canal front home with great boating, lobstering, fishing

Description: Our Island Thing... If you have a 'thing' for the islands of the Florida Keys then come have a fabulous get away at 'Our Island… More

Bedrooms: 3
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Key West Boat & Breakfast, Reef Sailing Trips, Island Trips Vacation Yacht Rental: 229193

Key West Boat & Breakfast, Reef Sailing Trips, Island Trips

Description: Located in Key West's Historic Seaport, choice of two sailboats for your dockside lodging. Your stay/sail charter includes 2 hour… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekend, From: 295  to  295 

*Rates Subject to Change

 

Charming Cudjoe Key Home-Crystal Clear Waterfront Canal-Boat/Swim Vacation House Rental: 230957

Charming Cudjoe Key Home-Crystal Clear Waterfront Canal-Boat/Swim

Description: This home located on one of the few deep water canals in the Lower Keys area.Crystal clear canals boasts 4 1/2 foot draft and can… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3500  to  4200 

*Rates Subject to Change

 

Spacious Ocean Front Resort - 3 Bedroom Condo Vacation Condo Rental: 232367

Spacious Ocean Front Resort - 3 Bedroom Condo

Description: This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a… More

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekend, From: 350  to  500 

*Rates Subject to Change

 

Venture Out, Gated Resort, Many Amenities Included Vacation House Rental: 232722

Venture Out, Gated Resort, Many Amenities Included

Description: Bright, colorful and tropical this freshly remodeled home is located within easy walking distance to convenience store and Olympic… More

Bedrooms: 1
Sleeps: 5

*Rates: nightly-weekend, From: 100  to  100 

*Rates Subject to Change

 

Casa Amor - 3BR Residence 2 Blocks from Duval Street Vacation House Rental: 233509

Casa Amor - 3BR Residence 2 Blocks from Duval Street

Description: Welcome to Casa Amor, our love nest for ten years has been converted into a vacation rental for you. We are located just two blocks… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 7500  to  9200 

*Rates Subject to Change

 

All Remaining 2011 dates only $79 a night!!! - Free Bikes Included!!! Vacation Studio Rental: 233787

All Remaining 2011 dates only $79 a night!!! - Free Bikes Included!!!

Description: Looking for the perfect affordable hide-away in Key West? Located in a remodeled Victorian Home - this guest room is just perfect… More

Bedrooms: 0
Sleeps: 2

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Bo's Tropical Get-a-Way at Venture Out in the Florida Keys Vacation House Rental: 234389

Bo's Tropical Get-a-Way at Venture Out in the Florida Keys

Description: Free use of two Ocean Kayaks during your stay. Dock your boat behind the 2 bedroom/2 bathroom nicely decorated rental unit on a deep… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Old Town location close to beach, shops & more Vacation Condo Rental: 234468

Old Town location close to beach, shops & more

Description: The Fort Zach condo has two bedrooms, one with a queen size bed and the second with two twin beds. The one bathroom has a tub with… More

Bedrooms: 2
Sleeps: 5

*Rates: weekly, From: 1100  to  2000 

*Rates Subject to Change

 

'Coral Isle' Beautiful 3Bed/3Bath Two Story Townhome at Coral Hammock Vacation Townhome Rental: 236965

'Coral Isle' Beautiful 3Bed/3Bath Two Story Townhome at Coral Hammock

Description: I am excited to offer our most recent addition of reasonably priced gorgeous homes located at Coral Hammock. Built in 2004, this… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekend, From: 175  to  175 

*Rates Subject to Change

 

To-Lu HideAway -- Best Keys Getaway on Open Water Vacation House Rental: 237303

To-Lu HideAway -- Best Keys Getaway on Open Water

Description: It doesn’t get more tropical than this!! There’s a palm tree in the middle of the house! Tropical bamboo interior throughout… More

Bedrooms: 3
Sleeps: 12

*Rates: weekly, From: 2000  to  2900 

*Rates Subject to Change

 

Bahama Gardens - Private Historic Old Town Vacation House Rental: 237487

Bahama Gardens - Private Historic Old Town

Description: The 'Main House' is a 2 story, 4 bedroom 1.5 bathroom renovated historic home. The house can accommodate 8 guests - 1 queen bed, 1… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 7000  to  8000 

*Rates Subject to Change

 

'Tropical Splendor' 3Bd/2Bth luxury condo & ocean view at King's Pointe Marina. Vacation Condo Rental: 238646

'Tropical Splendor' 3Bd/2Bth luxury condo & ocean view at King's Pointe Marina.

Description: Oceanside Condos at King's Pointe Marina is one of the most prestigious communities which offers breathtaking water views and large,… More

Bedrooms: 3
Sleeps: 7

*Rates: nightly-weekend, From: 215  to  215 

*Rates Subject to Change

 

Old Town Key West by Southernmost Beach and Duval Main Street. Vacation House Rental: 241481

Old Town Key West by Southernmost Beach and Duval Main Street.

Description: Prime Old Town Walking Location. Across the Street from Southernmost on the Beach, and down the Street from the Southernmost Point.… More

Bedrooms: 5
Sleeps: 12

*Rates: extra-night, From: 700  to  1000 

*Rates Subject to Change

 

Best Deal in Truman Annex - Cead Mile Failte Vacation Condo Rental: 241645

Best Deal in Truman Annex - Cead Mile Failte

Description: Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Tropical Cottage peacefully hidden amongst the palms and fragrant flowers. Vacation House Rental: 242624

Tropical Cottage peacefully hidden amongst the palms and fragrant flowers.

Description: Tropically landscaped with open water views. The minute you walk in the home invites you to simply relax and enjoy the laid back… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3500  to  3500 

*Rates Subject to Change

 

Rose Lane Villa - Grande, 1/2 block off Duval, Nightly rentals available! Vacation Condo Rental: 243689

Rose Lane Villa - Grande, 1/2 block off Duval, Nightly rentals available!

Description: Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekend, From: 419  to  449 

*Rates Subject to Change

 

Rose Lane Villa - Aqua, 1/2 block off Duval Vacation Condo Rental: 243693

Rose Lane Villa - Aqua, 1/2 block off Duval

Description: Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekend, From: 279  to  299 

*Rates Subject to Change

 

Rose Lane Villa's Villa Alta 1 bedroom, 1/2 block off Duval Vacation Villa Rental: 243695

Rose Lane Villa's Villa Alta 1 bedroom, 1/2 block off Duval

Description: Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekend, From: 159  to  179 

*Rates Subject to Change

 

Oceanfront Estate, Casa Aqua Mansion and Honeymoon Cottage Vacation Estate Rental: 245591

Oceanfront Estate, Casa Aqua Mansion and Honeymoon Cottage

Description: Casa Aqua is a Spanish Mediterranean estate on the ocean in the Lower Florida Keys. The mansion may be rented separately or with the… More

Bedrooms: 6
Sleeps: 12

*Rates: extra-night, From: 1200  to  1200 

*Rates Subject to Change

 

Boater's Paradise Vacation House Rental: 246870

Boater's Paradise

Description: New Construction. 3 bedrooms 2 full baths. Deep Water Boating Canal, easy access to Ocean. 2 blocks to Looe Key Reef Resort and… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool! Vacation Cottage Rental: 248921

Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool!

Description: Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple Properties in Key West Welcome to Petronia Palms! and… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Lily House located in the heart of Key West within walking distance everything Vacation House Rental: 249721

Lily House located in the heart of Key West within walking distance everything

Description: One of the best locations in key west located within walking distance to everything on the island , this charming home has all the… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Island Villa Vacation House Rental: 250258

Island Villa

Description: Relax and enjoy your Keys vacation in this spacious 5 bedroom 3 bath tri-level home. Gatherings will be especially memorable in and… More

Bedrooms: 5
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Marathon Island House Vacation House Rental: 250698

Marathon Island House

Description: Truly tropical paradise located just offshore. and dryer, BBQ with extra propane, outside sink and shower, linens, etc. Just bring… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Relax in Paradise Vacation Condo Rental: 251236

Relax in Paradise

Description: Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom, one bathroom unit has a spacious… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Best Key West Vacation Rentals, Truman Annex, Oceanside & More Vacation Condo Rental: 252089

Best Key West Vacation Rentals, Truman Annex, Oceanside & More

Description: Truman Annex Shipyard Condominium. 'Havana Views.' Two bedrooms/one full bathroom/sleeps maximum four people. Welcome to Kwjewel's… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Luxurious, Elegant, quiet Vacation House Rental: 253174

Luxurious, Elegant, quiet

Description: One of the most beautiful homes in Key West located on a wide canal with 35' of dock space available! Custom design heated pool.… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Top-floor Smathers Beach condo with gorgeous pool, tennis and steps from beach. Vacation Condo Rental: 254856

Top-floor Smathers Beach condo with gorgeous pool, tennis and steps from beach.

Description: Beach, Bath & Tennis! La Brisa is a gated oceanfront condo located across the street from Smathers Beach - one of only a few… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1400  to  2450 

*Rates Subject to Change

 

Key West luxury art deco style oceanside condo with pool and beach Vacation Condo Rental: 255720

Key West luxury art deco style oceanside condo with pool and beach

Description: This condo is one of the best 1800 Atlantic has to offer. Situated on the Atlantic Ocean in a tropical setting with lush… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Luxurious tropical courtyard view Condominium at 1800 Atlantic on the Ocean. Vacation Condo Rental: 257555

Luxurious tropical courtyard view Condominium at 1800 Atlantic on the Ocean.

Description: Luxurious tropical courtyard view two bedroom condo. This exceptional condo has a City of Key West Transient License which permits… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3500  to  6500 

*Rates Subject to Change

 

Bayside Beauty in Sugarloaf Key Vacation House Rental: 257918

Bayside Beauty in Sugarloaf Key

Description: Located in upscale South Point, overlooking Sugarloaf Sound and just 12 miles from Key West, this beautiful home offers you a… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 10500  to  10500 

*Rates Subject to Change

 

Petronia Palms for Budget Minded by Duval St Has a Large Pool! Vacation Cottage Rental: 258192

Petronia Palms for Budget Minded by Duval St Has a Large Pool!

Description: Welcome to the 'Sago Palm Cottage'! Note: Monthly Vacation Rental, I don't use the calendars, as I have multiple Properties in Key… More

Bedrooms: 0
Sleeps: 2

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Beautiful Oceanfront Home with Dock & Poolside Tiki Bar Vacation House Rental: 258472

Beautiful Oceanfront Home with Dock & Poolside Tiki Bar

Description: Island View is a charming three bedroom estate situated on three tropical landscaped lots that overlook the Atlantic Ocean and… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 6000  to  6900 

*Rates Subject to Change

 

Three Bedroom Private Home Vacation House Rental: 258917

Three Bedroom Private Home

Description: 'CASA ROYAL' allows you to live like a local. Completely renovated using quality finishings,this private single family home consists… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4500  to  7550 

*Rates Subject to Change

 

Oceanfront Condominium - Key West's Crown Jewel Vacation Condo Rental: 260572

Oceanfront Condominium - Key West's Crown Jewel

Description: We know that you will enjoy staying in our little bit of paradise - our home away from home - Key West's Crown Jewel. This is a… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 2300  to  2300 

*Rates Subject to Change

 

Truman Annex Best Location it Town Vacation Condo Rental: 260666

Truman Annex Best Location it Town

Description: Greetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3000  to  5400 

*Rates Subject to Change

 

Truman Annex Old Town Key West Waterfront Condo! Vacation Condo Rental: 261245

Truman Annex Old Town Key West Waterfront Condo!

Description: Beautiful Spacious Condo overlooking the Key West Harbor waterfront! - This exclusive condo is a part of Harbor Place, a waterfront… More

Bedrooms: 3
Sleeps: 7

*Rates: weekly, From: 2500  to  2500 

*Rates Subject to Change

 

Key West Conch Retreat Vacation Condo Rental: 261681

Key West Conch Retreat

Description: The Conch Retreat Condo is in the beautiful gated community of Truman Annex. It's within walking to Duval Street and the best beach… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1100  to  1100 

*Rates Subject to Change

 

Tropical Custom Home with Gorgeous Sunset Views Vacation House Rental: 264474

Tropical Custom Home with Gorgeous Sunset Views

Description: Enjoy a truly unique Florida Keys experience in this 3-bedroom, 2-bath home with a large tropical yard, beautifully landscaped with… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3600  to  4000 

*Rates Subject to Change

 

Beachfront with Awesome Atlantic Views Vacation House Rental: 265645

Beachfront with Awesome Atlantic Views

Description: Located in the fabulous string of islands called the Florida Keys on the open water. The best Bahia Honda beautiful sandy beach is… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 10000  to  10000 

*Rates Subject to Change

 

Quiet, modern condo close to the Atlantic Ocean Vacation Condo Rental: 265898

Quiet, modern condo close to the Atlantic Ocean

Description: Located approximately 3 miles from Duval Street and just a mile from Smather's beach this condo offers a good standard of… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 175  to  225 

*Rates Subject to Change

 

CHILMARK SOUTH - paradise found in truman annex! Vacation Condo Rental: 265962

CHILMARK SOUTH - paradise found in truman annex!

Description: From the minute you walk through the front door, you'll feel like you're in paradise. The view is spectacular day and night. Located… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1900  to  3500 

*Rates Subject to Change

 

Oceanview Retreat with Open Water View and Direct Boating Access Vacation House Rental: 266694

Oceanview Retreat with Open Water View and Direct Boating Access

Description: Two Bedroom Oceanview Retreat in Cudjoe Keywith Open Water View and Direct Boating Access. Great boating from concrete dock with… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2800  to  3200 

*Rates Subject to Change

 

2 Bed / 2 Bath Luxury Condo on the Ocean - Sleeps 6 (next to Smather's Beach) Vacation Condo Rental: 266703

2 Bed / 2 Bath Luxury Condo on the Ocean - Sleeps 6 (next to Smather's Beach)

Description: Beautifully remodeled, 1374 sq. ft., 2 bedroom (King Beds) 2Bath luxury condo located on the beach - SLEEPS 6. Gorgeously landscaped… More

Bedrooms: 2
Sleeps: 6

*Rates: extra-night, From: 265  to  390 

*Rates Subject to Change

 

Open Water View at Parrotfish Paradise Vacation House Rental: 267369

Open Water View at Parrotfish Paradise

Description: Very comfortable vacation home has it all! Concrete seawall with cut out for your boats, fast access to open water for fishing,… More

Bedrooms: 1
Sleeps: 7

*Rates: monthly, From: 3200  to  3200 

*Rates Subject to Change

 

Architect's Personal Residence, Private Pool, 1 Blk. to Duval Vacation … Rental: 267677

Architect's Personal Residence, Private Pool, 1 Blk. to Duval

Description: Completed in 1992, this two bedroom two bath home was designed by a local architect for the relaxed Key West tropical lifestyle.… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Gorgeous 3 Story 'OCEANFRONT' Home in Lower Keys (Cudjoe Key) Vacation House Rental: 268183

Gorgeous 3 Story 'OCEANFRONT' Home in Lower Keys (Cudjoe Key)

Description: This beautiful waterfront home is located in Jolly Roger Estates, directly on the Atlantic Ocean. Experience an amazing sunset view… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 5850  to  5850 

*Rates Subject to Change

 

5 Acre Oceanfront Tropical Paradise in the Middle of a Natural Wildlife Habitat Vacation House Rental: 268334

5 Acre Oceanfront Tropical Paradise in the Middle of a Natural Wildlife Habitat

Description: 5 acres, Very private, Luxury estate home. Elegantly decorated and lushly landscaped. This Amazing estate home includes outdoor… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 12000  to  12000 

*Rates Subject to Change

 

Unique Waterfront Dome Home with Pool and Amazing Sunrise Views Vacation House Rental: 268392

Unique Waterfront Dome Home with Pool and Amazing Sunrise Views

Description: This Unique Bayfront home offers amazing sunrise over the open water. The round shape of this home and many windows offers panoramic… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 7050  to  7050 

*Rates Subject to Change

 

Nice Waterfront Home on the Open Water of Pine Channel 'Little Torch Key' Vacation House Rental: 268798

Nice Waterfront Home on the Open Water of Pine Channel 'Little Torch Key'

Description: This open water 'BAYFRONT' home offers both sensational sunrise views overlooking the waters of Pine Channel and sunset views over… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4050  to  4050 

*Rates Subject to Change

 

Peaceful 2 BR Condo with All Amenities Vacation Condo Rental: 269736

Peaceful 2 BR Condo with All Amenities

Description: Enjoy the comforts of home in the midst of paradise. Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort.… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 110  to  175 

*Rates Subject to Change

 

Very quiet area, loads of room, great views and close to everything Vacation House Rental: 269748

Very quiet area, loads of room, great views and close to everything

Description: Openwater, Pool and Privacy are yours when you enter the gate to this 3 bedroom, 3 bath resort home located on Sugarloaf Key in the… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 7500  to  7500 

*Rates Subject to Change

 

TROPICAL ESCAPE Located on Cudjoe Key Vacation House Rental: 269759

TROPICAL ESCAPE Located on Cudjoe Key

Description: This two bedroom with small additional sleeping area - two bath canal home located on Cudjoe Key is ideal for a peaceful and quiet… More

Bedrooms: 2
Sleeps: 5

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Private House Facing The Ocean Vacation House Rental: 270477

Private House Facing The Ocean

Description: Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open.. This is a spacious… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 6500  to  7500 

*Rates Subject to Change

 

Enjoy an Affordable Blissful Keys Getaway! Vacation House Rental: 271572

Enjoy an Affordable Blissful Keys Getaway!

Description: Surrounded by beauty and tranquility, this spacious and updated 2 bedroom, 2 bath accommodation features its canal with easy access… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2000  to  2500 

*Rates Subject to Change

 

Ocean Front Summerland Estate Vacation Estate Rental: 271701

Ocean Front Summerland Estate

Description: Located along Millionaires Row on prestigious Summerland Key Florida, Summerland Estate is a state and county licensed weekly rental… More

Bedrooms: 5
Sleeps: 12

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Beautiful Oceanfront Property. Call for special multi month winter rental rates. Vacation House Rental: 271785

Beautiful Oceanfront Property. Call for special multi month winter rental rates.

Description: Newly Remodeled home with in ground heated pool. This 4 bedroom, 3 full baths, fully-furnished home is situated on the most… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 6700  to  7900 

*Rates Subject to Change

 

Private sunrises from this tropical bay estate Vacation House Rental: 271788

Private sunrises from this tropical bay estate

Description: NEW HEATED IN GROUND POOL TO BE READY BY AUGUST 2011. This 4 bedroom, 3 full bath, fully-furnished home is right on Bogie Channel on… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 4500  to  7700 

*Rates Subject to Change

 

180 degree ocean views. Call for special summer rates. Vacation House Rental: 271794

180 degree ocean views. Call for special summer rates.

Description: This property is having a new outdoor heated pool installed this summer, it will be ready by August. Step into paradise and leave… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4900  to  7200 

*Rates Subject to Change

 

Oceanfront Two Story Penthouse in Key West! Vacation Condo Rental: 272959

Oceanfront Two Story Penthouse in Key West!

Description: 'Key West Beach Club' is located on the Atlantic Ocean, This is a premier condominium property in Key West and this unit is a sought… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Key West - Truman Annex Cottage-Best Location on the Island-Newly Renovated! Vacation Townhome Rental: 273217

Key West - Truman Annex Cottage-Best Location on the Island-Newly Renovated!

Description: Pelican's Perch is conveniently located within walking distance to most everything in Key West. It has been remodeled with new… More

Bedrooms: 2
Sleeps: 5

*Rates: monthly, From: 5600  to  5600 

*Rates Subject to Change

 

Tropical Retreat Near Duval Street! Vacation House Rental: 273425

Tropical Retreat Near Duval Street!

Description: Authentic slice of Old Key West near Bahamas Village coupled with the modern amenities of new construction, this is our… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Ramrod Key Oceanfront House is just 30 minutes from Key West! Vacation House Rental: 274606

Ramrod Key Oceanfront House is just 30 minutes from Key West!

Description: Here is a get-away that surrounds you with all the comforts of home. Just 30 minutes north of Key West, 15 minutes from Bahia Honda… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1400  to  1400 

*Rates Subject to Change

 

Chalet D'Amour- All New 'Green' Luxury Cottage with Jacuzzi Vacation Cottage Rental: 275318

Chalet D'Amour- All New 'Green' Luxury Cottage with Jacuzzi

Description: Chalet D'Amour is part of the Travelers Palm Inn, a member of the Green Hotels Association. The 9' ceilings in our custom designed… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 2100  to  2300 

*Rates Subject to Change

 

Waterfront 3BR Beauty-Kayaks-Sun Porch-Easy Ocean Access Vacation House Rental: 276386

Waterfront 3BR Beauty-Kayaks-Sun Porch-Easy Ocean Access

Description: This fantastic 3 bedroom, 2 Bath home has a great wrap around porch. You can relax on the porch enjoying the sea breeze or barbecue… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 3990  to  3990 

*Rates Subject to Change

 

Casa Caracol-Beautiful New Cottage Just Blocks from Duval Street Vacation House Rental: 277296

Casa Caracol-Beautiful New Cottage Just Blocks from Duval Street

Description: Casa Caracol is part of The Travelers Palm Inn, a member of The Green Hotels Association. The 9' ceilings in our custom designed… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 2050  to  2250 

*Rates Subject to Change

 

Isla Bella-A Gorgeous Tropical Oasis with Parking & Jacuzzi Vacation House Rental: 277297

Isla Bella-A Gorgeous Tropical Oasis with Parking & Jacuzzi

Description: The 9' ceilings in our custom designed Isla Bella will add to your feeling of comfort and relaxation during your visit. This house… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 2050  to  2250 

*Rates Subject to Change

 

TIKI BEACH Charming OPEN WATER bungalow. Sunrises Pool Spa Beach Dock Kids Pets Vacation House Rental: 277348

TIKI BEACH Charming OPEN WATER bungalow. Sunrises Pool Spa Beach Dock Kids Pets

Description: Tiki Beach is a secluded 3 bedroom, 2 bath beach bungalow located on the Gulf side of the Island. Breathtaking sunrises from the… More

Bedrooms: 3
Sleeps: 9

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Boaters Paradise! Waterfront Key West Home Vacation House Rental: 277391

Boaters Paradise! Waterfront Key West Home

Description: Boat in, boat out. Inspired by Balinese design this private waterfront retreat has deep-water access and is the ultimate base for… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 1750  to  1750 

*Rates Subject to Change

 

Attitude Key West : Get that Chillin' Feeling Vacation Condo Rental: 279213

Attitude Key West : Get that Chillin' Feeling

Description: Reno's Completed May 2010! This unique unit is OUR VACATION HOME NOT JUST ANOTHER RENTAL. Located in the Ship Yard of Truman Annex a… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1050  to  1650 

*Rates Subject to Change

 

Sunset Palms with Open Water View of Pine Channel Vacation House Rental: 280388

Sunset Palms with Open Water View of Pine Channel

Description: Open Water property with great view and relaxing feel! Enjoy breathtaking sunsets through the palms in the evening with beverage in… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 4000  to  5000 

*Rates Subject to Change

 

Laid Back Florida Keys Living on Boating Canal Vacation … Rental: 280393

Laid Back Florida Keys Living on Boating Canal

Description: Florida Keys Living the way it should be! Located in Doctor`s Arm in a very nice and quiet neighborhood. Boating access to the… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 3000  to  3200 

*Rates Subject to Change

 

Carpe Diem- a tropical Conch Cottage in old town Key West - Vacation Cottage Rental: 281441

Carpe Diem- a tropical Conch Cottage in old town Key West -

Description: Located in the old town of Key West Carpe Diem is a quintessential Conch Cottage close to all attractions and only a few blocks from… More

Bedrooms: 1
Sleeps: 4

*Rates: monthly, From: 2000  to  4000 

*Rates Subject to Change

 

The Tree House - an authentic Key West experience. Vacation House Rental: 282583

The Tree House - an authentic Key West experience.

Description: If it is character you are seeking you have found your accommodations. This unique space occupies the entire 2nd floor of a historic… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 3000  to  4900 

*Rates Subject to Change

 

Beach House Bungalow Vacation House Rental: 284178

Beach House Bungalow

Description: Located on a private, quite, cul de sac, in the prestigious neighborhood of South Point, Beachside Bungalow is the Florida Keys… More

Bedrooms: 4
Sleeps: 12

*Rates: weekly, From: 3000  to  3000 

*Rates Subject to Change

 

Elegant Key West Getaway Vacation House Rental: 286317

Elegant Key West Getaway

Description: This MONTHLY RENTAL is a newly renovated two story traditional Key West home with attached guest cottage and was the former home of… More

Bedrooms: 4
Sleeps: 7

*Rates: monthly, From: 5750  to  9000 

*Rates Subject to Change

 

2/2 in a 5-Star Resort with Deepwater Canal Front Home Vacation House Rental: 286318

2/2 in a 5-Star Resort with Deepwater Canal Front Home

Description: Venture out lot 461 cudjo key.This is a 5 star Resort in a guarded community. The house is on a 35' Canal front, totally remodeled… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

My Blue Haven: 840 Lagoon Drive, Summerland Key, FL Vacation House Rental: 286339

My Blue Haven: 840 Lagoon Drive, Summerland Key, FL

Description: My Blue Haven is a Weekly Rental: Saturday-Saturday. My Blue Haven offers 4 bedrooms, 2 & 1/2 baths, a boat dock & more! Recently… More

Bedrooms: 4
Sleeps: 10

*Rates: monthly, From: 5600  to  5600 

*Rates Subject to Change

 

Torchview Florida Keys Secluded Paradise on Water Vacation House Rental: 289591

Torchview Florida Keys Secluded Paradise on Water

Description: Big Torch Key is reminiscent of the Keys 40 years ago, seclusion and peace invade your senses immediately, sunset views will take… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4000  to  6200 

*Rates Subject to Change

 

Brucie's Pristine Pool Peek is Paradise in Truman Annex Vacation Condo Rental: 290407

Brucie's Pristine Pool Peek is Paradise in Truman Annex

Description: This condo overlooks Truman Annex's lush landscaping & Shipyard pool. A short walk or bike ride to one of the best beaches on the… More

Bedrooms: 1
Sleeps: 2

*Rates: weekly, From: 1100  to  1100 

*Rates Subject to Change

 

Water views, step on your boat to Cuba!! Vacation House Rental: 290786

Water views, step on your boat to Cuba!!

Description: new 'Green' custom concrete elevated 2400 square ft ,3 BR/ 4 BA home, dual stairways, fenced/gated, open parking below. corner canal… More

Bedrooms: 3
Sleeps: 10

*Rates: monthly, From: 3000  to  3000 

*Rates Subject to Change

 

Roof top waterfront condo Key West between MM 10 just 5 min to KW Vacation Condo Rental: 293087

Roof top waterfront condo Key West between MM 10 just 5 min to KW

Description: Enjoy breathtaking sights and sounds from our penthouse condo, just 5 mi. outside of Key West. Our 672 sq. ft. efficient condo is… More

Bedrooms: 2
Sleeps: 6

*Rates: extra-night, From: 99  to  249 

*Rates Subject to Change

 

In a tropical setting on a canal is my beautiful manufactured home. Vacation Mobile_home Rental: 293149

In a tropical setting on a canal is my beautiful manufactured home.

Description: It is home for the famous Key Deer who are protected and can be seen roaming freely all over the island. Big Pine is also the home… More

Bedrooms: 2
Sleeps: 12

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Beautiful,Private, Tropical,On Acre With Plenty Of Wildlife Vacation House Rental: 293665

Beautiful,Private, Tropical,On Acre With Plenty Of Wildlife

Description: It is home for the famous Key Deer who are protected and can be seen roaming freely all over the island. Big Pine is also the home… More

Bedrooms: 3
Sleeps: 12

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

2 BR/ 2 BA in a 5 Star Resort with Ocean View Vacation House Rental: 294042

2 BR/ 2 BA in a 5 Star Resort with Ocean View

Description: This is a beautiful sparkling clean house located just 19 miles from Key West in a guarded community. Park your boat right behind… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Luxury 4 bedroom home with private pool and walking distance to beaches. Vacation House Rental: 294543

Luxury 4 bedroom home with private pool and walking distance to beaches.

Description: This 4 bedroom, 2 bath ranch style single family home is located 3 blocks from Smather's Beach and 5 blocks from Higgs Beach on the… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 4500  to  6800 

*Rates Subject to Change

 

Anderson's Key West Home Vacation House Rental: 294641

Anderson's Key West Home

Description: Beautiful vacation home in Key West Truman annex. Conveniently located two and a half blocks from Duval Street and Mallory Square.… More

Bedrooms: 4
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Captain's Hideout in Key West Vacation Villa Rental: 295290

Captain's Hideout in Key West

Description: Freshly redone, completed January 2009. Brand new high end furniture, including leather sofa and love seat. Brand new Beds, top of… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Brass Palm Villa, Private Luxury Home - ESCAPE TO PARADISE!! Vacation House Rental: 296145

Brass Palm Villa, Private Luxury Home - ESCAPE TO PARADISE!!

Description: Private Luxury Home with Heated Pool surrounded by lush tropical landscaping. Our vacation rental home is a fusion of Florida style… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5000  to  7800 

*Rates Subject to Change

 

Atlantic Mansion on Private Paradise Penisula Vacation House Rental: 297619

Atlantic Mansion on Private Paradise Penisula

Description: A Paradise treasure can be your vacation dream home! The dream of vacationing on the water on a tropical island has now come… More

Bedrooms: 4
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Private Luxury in Casa Marina Neighborhood Vacation House Rental: 298674

Private Luxury in Casa Marina Neighborhood

Description: The Casa Marina neighborhood is one of the most coveted residential areas in Historic Old Town Key West. Known for outstanding… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4000  to  8000 

*Rates Subject to Change

 

Rose Lane Villa's 'Villa Rosa' 1 bedroom, 1/2 block off Duval Vacation Villa Rental: 299233

Rose Lane Villa's 'Villa Rosa' 1 bedroom, 1/2 block off Duval

Description: Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekend, From: 149  to  169 

*Rates Subject to Change

 

Rose Lane Villa's Villa Vista 1 bedroom, 1/2 block off Duval Vacation Villa Rental: 299234

Rose Lane Villa's Villa Vista 1 bedroom, 1/2 block off Duval

Description: Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekend, From: 149  to  319 

*Rates Subject to Change

 

Rose Lane Villa's Villa Porta 1 bedroom, 1/2 block off Duval Vacation Villa Rental: 299236

Rose Lane Villa's Villa Porta 1 bedroom, 1/2 block off Duval

Description: Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekend, From: 149  to  169 

*Rates Subject to Change

 

Affordable, Charming, Quiet, Walking Distance to Town, Shopping, Dining, Beach Vacation Condo Rental: 299544

Affordable, Charming, Quiet, Walking Distance to Town, Shopping, Dining, Beach

Description: Tree Tops is a stylish and practical one bedroom condo located in the gated community of Truman Annex. Truman Annex is a popular and… More

Bedrooms: 1
Sleeps: 3

*Rates: weekly, From: 1000  to  1000 

*Rates Subject to Change

 

Downtown, Walking to everything, Close to Beach Vacation House Rental: 299550

Downtown, Walking to everything, Close to Beach

Description: DUPONT RETREAT is a bright and spacious 3 bedroom, 3 bath home has the best of everything with a private pool surrounded by lush… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2900  to  2900 

*Rates Subject to Change

 

Awesome Keys Waterfront Property with Fantastic Nightly Sunsets Vacation House Rental: 304890

Awesome Keys Waterfront Property with Fantastic Nightly Sunsets

Description: Enjoy spectacular bay views and sunsets from the comfort of this great home. Open floor plan creates the perfect place for… More

Bedrooms: 3
Sleeps: 9

*Rates: monthly, From: 4000  to  4500 

*Rates Subject to Change

 

Charming Keys Home on Canal with Great Boating Access to Ocean or Bay Vacation House Rental: 304891

Charming Keys Home on Canal with Great Boating Access to Ocean or Bay

Description: Tropical Keys home on Ramrod Key is an ideal spot for your vacation home. Cathedral ceilings, tropical colors, large kitchen, canal,… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2800  to  3200 

*Rates Subject to Change

 

IMAGINE CUDJOE KEY! Keys Down Time Vacation House Rental: 306221

IMAGINE CUDJOE KEY! Keys Down Time

Description: IMAGINE CUDJOE KEY! Imagine, as the mainland fades, and the Florida Keys island chain gracefully sweeps westerly toward the sunset.… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

5 bedroom Cudjoe Gardens Home.....Waterfront Paradise, Wifi Vacation House Rental: 307746

5 bedroom Cudjoe Gardens Home.....Waterfront Paradise, Wifi

Description: Located in beautiful Cudjoe Gardens, an upscale subdivision this large, beautiful (newly remodeled) custom island home is ground… More

Bedrooms: 5
Sleeps: 10

*Rates: monthly, From: 3000  to  3000 

*Rates Subject to Change

 

SUMMER DEALS!Exclusive waterfront acre home with heated pool &private boat dock! Vacation House Rental: 309489

SUMMER DEALS!Exclusive waterfront acre home with heated pool &private boat dock!

Description: 'The Overlook' at Big Pine Key is an exclusive private waterfront pool(heated) home located next to the Blue Heron and Key Deer… More

Bedrooms: 2
Sleeps: 10

*Rates: monthly, From: 4950  to  4950 

*Rates Subject to Change

 

Large Oceanfront Home, Heated Pool, Dock-Weekly/Monthly Vacation House Rental: 309804

Large Oceanfront Home, Heated Pool, Dock-Weekly/Monthly

Description: 'Seaclusion' is a unique 3000 square foot custom built home set on over an acre of tropical landscaping with a sparkling new heated… More

Bedrooms: 4
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

''The Oasis'' Water Front Home on Crystal Clear Swimmable Canal Vacation House Rental: 310443

''The Oasis'' Water Front Home on Crystal Clear Swimmable Canal

Description: Imagine yourself ''Midnight at the Oasis!'' This spacious, waterfront home is lushly landscaped on a deep water, swimming canal with… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

See & Hear Atlantic Ocean from Studio & King bed! ! Sunny! Beachy! See Horizons! Vacation Studio Rental: 311616

See & Hear Atlantic Ocean from Studio & King bed! ! Sunny! Beachy! See Horizons!

Description: Ocean is steps out your door!! You're going To Love it! Studio UP!~Kingbed has horizon view from your pillow!! ~NOTICE! Special… More

Bedrooms: 0
Sleeps: 2

*Rates: nightly-weekend, From: 219  to  339 

*Rates Subject to Change

 

Charming 'Conch Cottage' on Oceanfront Property Near Key West and Big Pine Key Vacation Cottage Rental: 313528

Charming 'Conch Cottage' on Oceanfront Property Near Key West and Big Pine Key

Description: This great family vacation spot near Key West is in the Florida Keys! Stay in the lovingly renovated two-bedroom 'Conch Cottage' on… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Oceanfront Bungalow, Dock 80'Heated Pool Deep Channel Tennis 15 min Key West Vacation Bungalow Rental: 315267

Oceanfront Bungalow, Dock 80'Heated Pool Deep Channel Tennis 15 min Key West

Description: Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the ocean and sitting out on a point with water… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 950  to  1700 

*Rates Subject to Change

 

Oceanfront Acre Heated Private Pool Beach Dock 15 Min Key West Vacation House Rental: 317093

Oceanfront Acre Heated Private Pool Beach Dock 15 Min Key West

Description: Cudjoe Key (15 minutes from Key West OR Bahia Honda State Park) 3 bedroom, 2 bath newer home with master suite having a double sink,… More

Bedrooms: 3
Sleeps: 10

*Rates: weekly, From: 1800  to  2950 

*Rates Subject to Change

 

Oceanfront Affordable Cottage with Dock, Kayaks and Pool Vacation Cottage Rental: 319584

Oceanfront Affordable Cottage with Dock, Kayaks and Pool

Description: Affordable clean, comfortable cottages just 20 miles from Key West. Located on the oceanfront. Housekeeping cottage with full… More

Bedrooms: 4
Sleeps: 18

*Rates: nightly-weekend, From: 200  to  200 

*Rates Subject to Change

 

Waterfront Home with Pool in Exclusive, Private Neighborhood in Lower Sugarloaf Vacation House Rental: 319597

Waterfront Home with Pool in Exclusive, Private Neighborhood in Lower Sugarloaf

Description: Luxury, 2300 sq. ft. pool home with large porch, overlooking canal and partial open-water view. Three bedrooms and two baths. One… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 6000  to  6000 

*Rates Subject to Change

 

Old Town Truman & Duval Townhome Vacation House Rental: 320640

Old Town Truman & Duval Townhome

Description: Large secluded Old Town Conch-Style town home is located on Truman Avenue just one block from Duval Street. First floor has a… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Beautiful Waterfront Single Family Home - 5 miles from Key West Vacation House Rental: 322888

Beautiful Waterfront Single Family Home - 5 miles from Key West

Description: This is a beautiful Spanish style home on a clean swimming canal 9 miles from Duval Street, Key West. Our home is just 4 houses from… More

Bedrooms: 3
Sleeps: 6

*Rates: extra-night, From: 150  to  150 

*Rates Subject to Change

 

Real World MTV House---Not Just a House Your Own Private Resort Vacation House Rental: 326563

Real World MTV House---Not Just a House Your Own Private Resort

Description: This isn't just a house, this is your own private mini resort in Key West, Florida. THERE IS NO OTHER PROPERTY THAT COMPARES TO THIS… More

Bedrooms: 7
Sleeps: 20

*Rates: monthly, From: 30000  to  30000 

*Rates Subject to Change

 

Modern Luxury and Privacy Just Steps from Duval Vacation House Rental: 326701

Modern Luxury and Privacy Just Steps from Duval

Description: Would you enjoy truly modern luxury within walking distance to Key West's best restaurants, clubs, and art galleries? If so, this is… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 2500  to  2500 

*Rates Subject to Change

 

Ocean Retreat Vacation Townhome Rental: 327107

Ocean Retreat

Description: Private Home One of the nicest rentals in Key West. Close to Ocean and beach. Access to large private association pool. Three blocks… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2900  to  4400 

*Rates Subject to Change

 

Ocean Paradise Vacation House Rental: 327109

Ocean Paradise

Description: This is a One Week Minimum Stay!!! Three bedroom four bath private home. Heated Pool with massage water jets and special colored… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 4400  to  5900 

*Rates Subject to Change

 

Pool, Dock, Sandy Beach, Privacy, Open Water Estate Vacation House Rental: 327552

Pool, Dock, Sandy Beach, Privacy, Open Water Estate

Description: Unique estate property that has it all. Dockage, sandy beach, shopping, scuba diving, off shore fishing, back country tarpon… More

Bedrooms: 7
Sleeps: 14

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Pink Iguana - Beautiful Fairway View...Location...Location Vacation Townhome Rental: 328375

Pink Iguana - Beautiful Fairway View...Location...Location

Description: The neighborhood is beaming with colorful Conch style, white picket fenced homes, lush tropical plants, resort style tranquil pools,… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Very Private Location, American Caribbean, with Tropical Water Views Vacation House Rental: 328944

Very Private Location, American Caribbean, with Tropical Water Views

Description: Beautiful Florida Key Vacation Home, The American Caribbean , on Mile Marker 26 on Ram Rod Key, Florida Very Private Location!… More

Bedrooms: 3
Sleeps: 7

*Rates: extra-night, From: 250  to  250 

*Rates Subject to Change

 

Dock Your Boat at Canal Front Home / Ocean Side of Ramrod Key Vacation House Rental: 329055

Dock Your Boat at Canal Front Home / Ocean Side of Ramrod Key

Description: Take your boat from the dock for Quick and easy access to the Ocean, Snorkeling/Diving at Looe Key, and the Fishing in the warm… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2500  to  2500 

*Rates Subject to Change

 

Casa Colonial Island Luxury in Key West Vacation House Rental: 329361

Casa Colonial Island Luxury in Key West

Description: Casa Colonial is Key West Luxury at its best! Nestled in a quite residential neighborhood, this amazing three story colonial house… More

Bedrooms: 3
Sleeps: 7

*Rates: monthly, From: 10500  to  10500 

*Rates Subject to Change

 

Mojitoville: Pet-Friendly Old Town Cottage W/ Private Pool Vacation House Rental: 330102

Mojitoville: Pet-Friendly Old Town Cottage W/ Private Pool

Description: The historic cottage features two bedrooms, one with king pillow top bed , 27 inch flat screen CATV and the other with queen pillow… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 4000  to  4000 

*Rates Subject to Change

 

Key West La Brisa Condominuim Vacation Condo Rental: 330812

Key West La Brisa Condominuim

Description: www. keywestlabrisacondo.com La Brisa Condominium is located on S. Roosevelt Blvd. across the largest beach in Key West, Smathers… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Located on Key West golf course, newly decorated & modern, fully furnished Vacation Townhome Rental: 331171

Located on Key West golf course, newly decorated & modern, fully furnished

Description: 3 Bedrooms/2 Bath also roll away couch so sleeps 8 comfortably. Large Deck with Screened in porch. BBQ Grill, Washer/Dryer,… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 3250  to  3250 

*Rates Subject to Change

 

Simonton Studio, an Old Town get-away for 2. New Pricing Vacation Studio Rental: 332511

Simonton Studio, an Old Town get-away for 2. New Pricing

Description: This Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West.… More

Bedrooms: 0
Sleeps: 2

*Rates: weekly, From: 675  to  1500 

*Rates Subject to Change

 

Luxury Key West Home Vacation House Rental: 332855

Luxury Key West Home

Description: Completely Renovated Luxury Conch Home In Old Town. Fabulous Pool And Manicured Grounds. Double Lot. Hardwood Floors, High Ceilings,… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 12000  to  20000 

*Rates Subject to Change

 

Great Fishing & Snorkeling Area in Paradise Vacation House Rental: 334096

Great Fishing & Snorkeling Area in Paradise

Description: Lovely 2 bedroom/ 2 bath home in paradise with tropical plants. This location is a boaters dream. It is secluded off main highway.… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 3800  to  3800 

*Rates Subject to Change

 

Canalfront Home On A Quiet Street, Only Minutes From Key West. Vacation House Rental: 334334

Canalfront Home On A Quiet Street, Only Minutes From Key West.

Description: Situated on one of the quietest streets on Lower Sugarloaf Key, this home is the perfect vacation getaway. It's canalfront location… More

Bedrooms: 3
Sleeps: 10

*Rates: monthly, From: 3500  to  3500 

*Rates Subject to Change

 

Lovely waterfront stilt home on a canal with Atlantic and Gulf of Mexico access Vacation House Rental: 335179

Lovely waterfront stilt home on a canal with Atlantic and Gulf of Mexico access

Description: Beautiful 2 bedroom 2 bath canal front home in the Florida Keys! A 35ft waterfront complete with whips, dock posts, cleats, and a… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Hollinsed House - Key West Old Town - Great Location!! Vacation Studio Rental: 335841

Hollinsed House - Key West Old Town - Great Location!!

Description: Beauty and economy in the heart of Old Town Key West! Ideally located just one block from famous Duval Street, this ground floor… More

Bedrooms: 0
Sleeps: 2

*Rates: nightly-weekend, From: 148  to  228 

*Rates Subject to Change

 

Quiet waterfront condo with boat slip, beach and pool! One of a kind! Vacation Condo Rental: 335989

Quiet waterfront condo with boat slip, beach and pool! One of a kind!

Description: Beautiful condo centrally located in Key West. Huge master suite overlooking beach and pool. Second bedroom has private entrance.… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 3500  to  4500 

*Rates Subject to Change

 

Deluxe 3 BR Villa at Fort Zach Beach in Historic Old Town Key West Sleeps 1 - 16 Vacation Villa Rental: 336442

Deluxe 3 BR Villa at Fort Zach Beach in Historic Old Town Key West Sleeps 1 - 16

Description: Please include your phone numbers with your inquiry (required), even if you are overseas... Since there are three completely self… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 2800  to  2800 

*Rates Subject to Change

 

Private Estate Waterfront Paradise with Dock & Heated Pool Vacation House Rental: 336563

Private Estate Waterfront Paradise with Dock & Heated Pool

Description: Magnificent sunsets and views from a isolated eco-friendly environment. Located on quiet Big Torch Key just 30 minutes from Key… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Lovely, private, Conch home in lush tropical garden setting Vacation House Rental: 336821

Lovely, private, Conch home in lush tropical garden setting

Description: Lovely, private, conch home in a lush, tropical garden setting located less than 10 min. walk to Smathers ocean beach. Here you can… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 7500  to  8000 

*Rates Subject to Change

 

Designer Dream 2BR/2BA with Heated Pool and Concierge Vacation House Rental: 337059

Designer Dream 2BR/2BA with Heated Pool and Concierge

Description: Charming house in Old town near the cemetery and 3 blocks from Duval. Just one 1 block from Seven Fish! Complete renovation in 2006… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Charming, downtown, walking distance to all activities, quiet, gated community Vacation Condo Rental: 337570

Charming, downtown, walking distance to all activities, quiet, gated community

Description: Crocodile Ranch is a 2 bedroom 1 bath, lower level, renovated 'Shipyard' home located in the Truman Annex. This is a perfect… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1100  to  1600 

*Rates Subject to Change

 

Live like the locals in Key West Vacation House Rental: 337968

Live like the locals in Key West

Description: Located in a private compound, this home features a lovely shared garden along with a side patio area. This two story home has tile… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3500  to  3500 

*Rates Subject to Change

 

Big Pine Key Tropical Paradise Vacation House Rental: 338868

Big Pine Key Tropical Paradise

Description: This is a very charming, cozy place to spend your relaxing keys vacation. On a beautiful swimming canal, with dockage and great… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Large Waterfront House with a Nice Dock for Your Boat Vacation House Rental: 339439

Large Waterfront House with a Nice Dock for Your Boat

Description: This is a beautiful 6 year old house in front of the water where you can: 1. Park your boat on the dock and go to the Gulf (25 min)… More

Bedrooms: 3
Sleeps: 12

*Rates: weekly, From: 1500  to  1500 

*Rates Subject to Change

 

Tropical and Elegant Key West House Vacation … Rental: 339863

Tropical and Elegant Key West House

Description: The house is the essence of Key West elegant and tropical in the same breath of sea air as the beach is only minutes away as is… More

Bedrooms: 1
Sleeps: 8

*Rates: weekend, From: 2100  to  2100 

*Rates Subject to Change

 

Sunshine Luxury Suite with 2 Free Bikes & Garage Vacation Condo Rental: 340691

Sunshine Luxury Suite with 2 Free Bikes & Garage

Description: My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1000  to  1000 

*Rates Subject to Change

 

Perfect Spot for 2 Near Key West ~ Some Open Water Views & Free Wi-Fi Vacation Apartment Rental: 341202

Perfect Spot for 2 Near Key West ~ Some Open Water Views & Free Wi-Fi

Description: Located just outside of Key West...Some open water views from this clean and comfortable 2 bedroom/1 bath canal front apartment in… More

Bedrooms: 2
Sleeps: 2

*Rates: monthly, From: 1895  to  2795 

*Rates Subject to Change

 

Truman Annex Three Story Townhouse ~ Private..Yet Close To Mallory Sq & Duval St Vacation Townhome Rental: 341240

Truman Annex Three Story Townhouse ~ Private..Yet Close To Mallory Sq & Duval St

Description: 'ABALONE' ~ This antique, Bostonian style Foundry Townhome is located just steps away from “Truman’s Little White House”. Vaulted… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1800  to  1800 

*Rates Subject to Change

 

Fantastic Pool Home on Deep Water Canal in Summerland Key Vacation House Rental: 341950

Fantastic Pool Home on Deep Water Canal in Summerland Key

Description: This home has a split floor plan with 5 bedrooms and 3 full bathrooms - Great layout for multiple families visiting together. This… More

Bedrooms: 5
Sleeps: 12

*Rates: monthly, From: 4500  to  4500 

*Rates Subject to Change

 

Casa De Vino - 3 bedroom town home with resort pool Vacation Townhome Rental: 342717

Casa De Vino - 3 bedroom town home with resort pool

Description: Fine yet affordable accommodation located in the gated community of Coral Hammock known for its well manicured lush tropical… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 1395  to  1995 

*Rates Subject to Change

 

Charming Key West townhome with all the comforts of home. Vacation Townhome Rental: 342727

Charming Key West townhome with all the comforts of home.

Description: This townhome is located in the award-winning community The Truman Annex. The Truman Annex encompasses stately homes, luxury… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4800  to  4800 

*Rates Subject to Change

 

Quiet, elegant, Key West Condo close to the Ocean Vacation Condo Rental: 342925

Quiet, elegant, Key West Condo close to the Ocean

Description: This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1085  to  1365 

*Rates Subject to Change

 

Gorgeous Waterfront Townhome Vacation Townhome Rental: 343165

Gorgeous Waterfront Townhome

Description: This luxurious 4 level waterfront townhome is located on Garrison Bight in Old Town Key West. The home features high ceilings, maple… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Windsor Townhome Vacation Townhome Rental: 343167

Windsor Townhome

Description: Luxury & Sophistication are apparent as you enter this deluxe townhome, centrally located in a quiet Old Town neighborhood only 4… More

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekend, From: 445  to  445 

*Rates Subject to Change

 

Tropical, Cozy, & Fun Vacation Home on a clean private Gulf Swimming Canal! Vacation Mobile_home Rental: 344464

Tropical, Cozy, & Fun Vacation Home on a clean private Gulf Swimming Canal!

Description: This great 2 bedroom mobile home is situated in a terrific private community 'off the main tourist path' with your own personal dock… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 1500  to  2200 

*Rates Subject to Change

 

Ballyhoo Shores - Open Water Oasis Vacation House Rental: 344495

Ballyhoo Shores - Open Water Oasis

Description: Ballyhoo Shores is located at MM17 on Sugarloaf Sound. Luxury and spectacular sunsets await you in this West Indies style retreat.… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 6000  to  6000 

*Rates Subject to Change

 

One of a kind estate in the heart of old town Key West! Vacation Townhome Rental: 346785

One of a kind estate in the heart of old town Key West!

Description: Experience the uniqueness of Key West by staying at one of Key West Hideaways one of a kind vacation rentals. When you're ready to… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekend, From: 438  to  438 

*Rates Subject to Change

 

Incredible, peaceful, Florida Keys getaway home with an exclusive private beach! Vacation Estate Rental: 346961

Incredible, peaceful, Florida Keys getaway home with an exclusive private beach!

Description: As the sun rises in the east the soft clouds, like the cotton candy of endless childhood summers, illuminate with a thousand… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Beautiful, Quiet Summerland Key Getaway!!!! On a Private Airstrip!!! Low Rate! Vacation House Rental: 351816

Beautiful, Quiet Summerland Key Getaway!!!! On a Private Airstrip!!! Low Rate!

Description: Located on South Airport Drive in Summerland Key, Florida... Approximately 25 miles north of Key West 25 miles south of Marathon.… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 1200  to  1200 

*Rates Subject to Change

 

Stock Island Waterfront Condo with a Boat Slip Vacation Condo Rental: 352086

Stock Island Waterfront Condo with a Boat Slip

Description: Like Old Key West Your waterfront vacation place is in the most unique mixed use marina community in the Keys. Watch the fishing… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 1550  to  1550 

*Rates Subject to Change

 

Cozy cottage with a wonderful outdoor covered screened porch and private garden Vacation Cottage Rental: 353644

Cozy cottage with a wonderful outdoor covered screened porch and private garden

Description: Cozy Cottage with a wonderful outdoor covered screened porch, private garden, and bricked driveway. The interior is newly painted,… More

Bedrooms: 1
Sleeps: 4

*Rates: monthly, From: 3000  to  3000 

*Rates Subject to Change

 

Waterfront Big Pine Key Paradise Vacation House Rental: 353829

Waterfront Big Pine Key Paradise

Description: Our 2 bedroom/2 bath vacation rental sleeps 6 and is located in the exclusive Doctors Arm area of Big Pine Key, in the lower keys,… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3000  to  3500 

*Rates Subject to Change

 

The Best 2 BR Truman/Shipyard, Fort Zach Beach, Mallory, Duval Vacation Condo Rental: 353906

The Best 2 BR Truman/Shipyard, Fort Zach Beach, Mallory, Duval

Description: Fantastic 1st floor (garden level) condo in the best location in Key West! Holiday Dance is an end unit (extra windows and light) in… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Canal Front, Boat lift, Sunny and Large, Master Suite, HDTV, Fully Furnished Vacation House Rental: 355187

Canal Front, Boat lift, Sunny and Large, Master Suite, HDTV, Fully Furnished

Description: Welcome to the tropical island of Key West, Florida, the perfect destination for travelers looking for relaxation and comfort, or… More

Bedrooms: 3
Sleeps: 12

*Rates: monthly, From: 6000  to  6000 

*Rates Subject to Change

 

Wonderful Open Water Views of Cudjoe Bay and Sunsets Vacation House Rental: 356520

Wonderful Open Water Views of Cudjoe Bay and Sunsets

Description: Awesome sparkling open water views from this home located on a large corner lot in Cudjoe Key with great concrete dock. Large yard… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3500  to  4500 

*Rates Subject to Change

 

Lowest rates for Luxury home with pool in Key West, quiet, close to everything Vacation Condo Rental: 356987

Lowest rates for Luxury home with pool in Key West, quiet, close to everything

Description: This condo is located in Coral Hammock one of the newest gated communities in Key West. Located at 'mile marker 5' across from the… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 955  to  955 

*Rates Subject to Change

 

Charming Caretaker's Apartment in Old Town Vacation … Rental: 359005

Charming Caretaker's Apartment in Old Town

Description: This caretaker's apartment is in Old Town Key West, removed from the noise but close to all the attractions. Four blocks from Duval,… More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 665  to  665 

*Rates Subject to Change

 

Carefree, Tropical, Breezy, Casual, Quiet, Peaceful Vacation House Rental: 359521

Carefree, Tropical, Breezy, Casual, Quiet, Peaceful

Description: Immaculate 3 BR/2BA vacation rental home on Cudjoe Key, south of MM23 Oceanside, a quick 20 minute trip into Key West. Fully… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2400  to  3500 

*Rates Subject to Change

 

Cheerful Truman Annex Home Vacation Townhome Rental: 359528

Cheerful Truman Annex Home

Description: A beautifully furnished and comfortable town home, located within the prestigious President`s Walk at Truman Annex. The first floor… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 350  to  385 

*Rates Subject to Change

 

Barry Beach - Keys Cottage on Pine Channel W/Heated Pool Vacation House Rental: 359795

Barry Beach - Keys Cottage on Pine Channel W/Heated Pool

Description: This cottage was built in 1965 and still looks original on the outside, but has been updated inside for your comfort. The ground… More

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Charming Little Gem with Big Waterfront Location Vacation Mobile_home Rental: 360752

Charming Little Gem with Big Waterfront Location

Description: This wonderfully updated mobile unit is located in a great location and neighborhood that is close to the open water in the Gulf.… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2000  to  2500 

*Rates Subject to Change

 

Your Waterfront Paradise ** Autumn Special** Vacation House Rental: 361012

Your Waterfront Paradise ** Autumn Special**

Description: If There is Magic in the World, it Can Be Found at My Waterfront Oasis in Big Pine Key. Whether You Are in Search of a Cozy Romantic… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3100  to  3300 

*Rates Subject to Change

 

Boli Townhouse - a Key West Luxury Rental Vacation Townhome Rental: 364315

Boli Townhouse - a Key West Luxury Rental

Description: Boli Townhouse is located in the Truman Annex, a gated community in downtown old Key West. The Boli Townhouse is a two bedroom (a… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 5500  to  7200 

*Rates Subject to Change

 

Key West Waterfront Rental Vacation House Rental: 365011

Key West Waterfront Rental

Description: Welcome to Our Vacation Home! This property has been our Family Vacation home since we built it in 1978 and we are Happy to share it… More

Bedrooms: 9
Sleeps: 16

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Bahama Royal - 3 Bedroom with Pool Vacation House Rental: 365603

Bahama Royal - 3 Bedroom with Pool

Description: This home has all the charm of Key West with all the comforts needed for a great vacation. The house was been renovated. We saved… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 6500  to  7500 

*Rates Subject to Change

 

Ocean Breeze Suites Vacation Condo Rental: 367100

Ocean Breeze Suites

Description: The Galleon Resort in Key West is a Perfect Resort for You, Your Guests and Your Family. The unit is spacious and very beautiful.… More

Bedrooms: 3
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

New Potter's Cottage -Private Pool, Quiet, Yet Steps Off Duval Vacation House Rental: 367117

New Potter's Cottage -Private Pool, Quiet, Yet Steps Off Duval

Description: Key West Potter's Cottage. New owners for 2011. The property has been updated with new furniture, new beds, painted and decorated.… More

Bedrooms: 2
Sleeps: 5

*Rates: nightly-weekend, From: 300  to  330 

*Rates Subject to Change

 

Spacious Luxury Home with Pool Vacation House Rental: 368235

Spacious Luxury Home with Pool

Description: Comfortable home with over 2800 feet of living area on a canal with ocean or gulf access. Enjoy the Caribbean breezes and sunset… More

Bedrooms: 5
Sleeps: 10

*Rates: weekly, From: 1500  to  2000 

*Rates Subject to Change

 

Caribbean Soul Vacation House Rental: 368346

Caribbean Soul

Description: Fabulous Old Town Key West home just blocks from the famous Southernmost Point, Hemingway House, Duval Street, Lighthouse, Beaches &… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5500  to  9000 

*Rates Subject to Change

 

SUNNY STAY a quiet relaxing getaway overlooking gorgeous resort pool. Vacation Townhome Rental: 368347

SUNNY STAY a quiet relaxing getaway overlooking gorgeous resort pool.

Description: Located in the gated community of Coral Hammock lush with beautifullly maintained tropical vegetation and just a fews miles from Old… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekend, From: 185  to  275 

*Rates Subject to Change

 

Turquoise Mermaid ~ Old Town Key West Vacation Condo Rental: 368424

Turquoise Mermaid ~ Old Town Key West

Description: VACATION... like a local in Old Town Key West just a few short blocks from the Historic Seaport area where you will find waterfront… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 3000  to  6500 

*Rates Subject to Change

 

Breathtaking Waterfront Home, Dock, Open Water & 2 Canals! Vacation House Rental: 369579

Breathtaking Waterfront Home, Dock, Open Water & 2 Canals!

Description: Change Your Whole Latitude. Parrot Heads Welcome! 24 miles from Margaritaville. Close to interactive Dolphin Research Center. Fish… More

Bedrooms: 2
Sleeps: 8

*Rates: extra-night, From: 250  to  350 

*Rates Subject to Change

 

'Mango Gardens' Charming, Walking Distance to Duval, and Historic Seaport Area Vacation House Rental: 369876

'Mango Gardens' Charming, Walking Distance to Duval, and Historic Seaport Area

Description: Mango Gardens is a charming historic remodeled home located in Old Town, Key West. Private and spacious home has hardwood floors… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 4000  to  6825 

*Rates Subject to Change

 

Charming, quiet, Old Town, walking distance to everything Vacation Cottage Rental: 369947

Charming, quiet, Old Town, walking distance to everything

Description: PALM COURT - The Cottage: Sleeps Four - Our cottage is tastefully furnished with a mixture of antiques, oriental rugs and original… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

South Asian Retreat in a Key West Conch Cottage - Namaste Key West Vacation Cottage Rental: 373062

South Asian Retreat in a Key West Conch Cottage - Namaste Key West

Description: Key West has all of the charms of being away from the world, yet with all of the worldly conveniences near at hand. Located in the… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2500  to  4000 

*Rates Subject to Change

 

Tom's Parrot Perch: CURRENTLY UNDERGOING A GUT RENOVATION!! Vacation Condo Rental: 375693

Tom's Parrot Perch: CURRENTLY UNDERGOING A GUT RENOVATION!!

Description: Located only two minutes from the airport and five minutes from downtown the area truly offers the best of both worlds, close to… More

Bedrooms: 2
Sleeps: 6

*Rates: extra-night, From: 270  to  380 

*Rates Subject to Change

 

Luxury and Spacious Cuban Club Condo located on Duval Steet Vacation Condo Rental: 377448

Luxury and Spacious Cuban Club Condo located on Duval Steet

Description: We know that you will enjoy staying in this oasis of comfort in the paradise of Key West. Our Cuban Club Condo is a 1500sq ft, 20ft… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

My Condo by the Beach with Ocean View Vacation Condo Rental: 379068

My Condo by the Beach with Ocean View

Description: The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen… More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 950  to  1500 

*Rates Subject to Change

 

Affordable Luxury Beachfront Condo with Olympic Pool, Tennis Courts, Spa Vacation Condo Rental: 379354

Affordable Luxury Beachfront Condo with Olympic Pool, Tennis Courts, Spa

Description: Enjoy all the amenities at 1800 Atlantic Condominiums without breaking the bank! Our island view condo sleeps 4-6 and has everything… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1100  to  1100 

*Rates Subject to Change

 

Quietly Relax and Feel the Comfort at 'Casa Jose' Vacation House Rental: 379927

Quietly Relax and Feel the Comfort at 'Casa Jose'

Description: Come to our house and find a completely renovated 2 BR/2 BA stilt house that overlooks a 40 ft. lap pool and 75 ft. canal front for… More

Bedrooms: 2
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Big Pine Escape in Quiet Doctors Arm Vacation House Rental: 380700

Big Pine Escape in Quiet Doctors Arm

Description: The property has direct access to either the Atlantic Ocean or the Gulf in minutes, providing some of the finest blue water fishing… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2500  to  2500 

*Rates Subject to Change

 

Enjoy Your Own Mini Resort with Private Beach Vacation House Rental: 380818

Enjoy Your Own Mini Resort with Private Beach

Description: Enjoy your own private mini resort with its own private beach. Tremendous fun and peacefulness are both available. Wonderful views… More

Bedrooms: 4
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Truman Annex Key West D & D's Paradise Vacation Condo Rental: 382707

Truman Annex Key West D & D's Paradise

Description: This two bedroom fully-furnished condominium is located in Truman Annex, a private and quiet gated community of Private homes and… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Palm Court is located in historic Old Town Key West, just two blocks from Duval Vacation Bungalow Rental: 385057

Palm Court is located in historic Old Town Key West, just two blocks from Duval

Description: Our Guest Suite is a one-bedroom suite with queen-size bed and a living room with sleeper sofa for an extra guest. It is furnished… More

Bedrooms: 1
Sleeps: 3

*Rates: nightly-weekend, From: 199  to  199 

*Rates Subject to Change

 

Beach Club Penthouse Vacation Condo Rental: 385102

Beach Club Penthouse

Description: Enjoy the sights and scents of the Atlantic Ocean from this stunning penthouse located in the Key West Beach Club. Stylishly… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3500  to  7500 

*Rates Subject to Change

 

Southernmost Belle a Grand home in Historic Old Town Key West Vacation House Rental: 387301

Southernmost Belle a Grand home in Historic Old Town Key West

Description: Grand historic home in historic seaport area of Old Town Key West. Tucked behind a canopy of palms & fencing this home has a unique… More

Bedrooms: 5
Sleeps: 10

*Rates: nightly-weekend, From: 600  to  1000 

*Rates Subject to Change

 

Luxurious Garden Home Paradise with Pool in Midtown Key West Vacation House Rental: 388391

Luxurious Garden Home Paradise with Pool in Midtown Key West

Description: Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3000  to  4600 

*Rates Subject to Change

 

'CONCH CASA GRANDE @ TRUMAN ANNEX': Grand 7BR/7BA Home, 6 Master Suites... Vacation House Rental: 390171

'CONCH CASA GRANDE @ TRUMAN ANNEX': Grand 7BR/7BA Home, 6 Master Suites...

Description: Conch Casa Grande might well be the largest home available for vacation rental in the Truman Annex, which is appealing to anyone who… More

Bedrooms: 7
Sleeps: 12

*Rates: monthly, From: 24000  to  40000 

*Rates Subject to Change

 

“AZURE AFTERNOON @ OCEANSIDE MARINA': 3BR/2BA Oceanfront Condo, Pool & Spa... Vacation House Rental: 390173

“AZURE AFTERNOON @ OCEANSIDE MARINA': 3BR/2BA Oceanfront Condo, Pool & Spa...

Description: Your spacious oceanfront balcony will be a front row seat for a panorama of azure blue ocean and sky. With direct views of the ocean… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5000  to  9250 

*Rates Subject to Change

 

“FALLING WATER @ THE SEAPORT': Luxury 5BR/4.5BA Compound, Pool & Hot Tub... Vacation House Rental: 390174

“FALLING WATER @ THE SEAPORT': Luxury 5BR/4.5BA Compound, Pool & Hot Tub...

Description: From the street, you would never guess what lies beyond the gate: a dazzling residential compound with three custom-designed… More

Bedrooms: 5
Sleeps: 10

*Rates: monthly, From: 14000  to  22000 

*Rates Subject to Change

 

'OLD TOWN OASIS @ TRUMAN ANNEX': Spacious 2BR/2BA Oceanfront Condo w/Pool Vacation Condo Rental: 390175

'OLD TOWN OASIS @ TRUMAN ANNEX': Spacious 2BR/2BA Oceanfront Condo w/Pool

Description: What if you could stay right on the dock in Old Town but with the quiet and solitude of an exclusive gated community? The Green… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 6000  to  10500 

*Rates Subject to Change

 

'COLORFUL CONCH @ THE SANCTUARY': Immaculate 4BR/3BA Private Home, Pool... Vacation House Rental: 390176

'COLORFUL CONCH @ THE SANCTUARY': Immaculate 4BR/3BA Private Home, Pool...

Description: This beautiful private home has everything you could want in a vacation home. It has been meticulously furnished and maintained… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 5000  to  11000 

*Rates Subject to Change

 

“WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA PenthouseCondo... Vacation Condo Rental: 390177

“WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA PenthouseCondo...

Description: Directly facing the Gulf of Mexico right next to Mallory Square, this beautiful penthouse condo is the perfect place to spend your… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 8500  to  14000 

*Rates Subject to Change

 

“THE AVIARY NEST @ ARONOVITZ LANE': 2BR/2BA Cottage in Old Town, Pool... Vacation House Rental: 390178

“THE AVIARY NEST @ ARONOVITZ LANE': 2BR/2BA Cottage in Old Town, Pool...

Description: This charming conch cottage is located on 404 Aronovitz Lane, a little cul-de-sac just off Angela Street half a block from Duval.… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4400  to  8500 

*Rates Subject to Change

 

'VILLA MODERNE @ VONPHISTER': 4BR/4BA Luxury Home with Pool by Beach... Vacation House Rental: 390179

'VILLA MODERNE @ VONPHISTER': 4BR/4BA Luxury Home with Pool by Beach...

Description: 'Villa Moderne @ Vonphister' is located just a block from White Street in a quiet neighborhood away from the crowds, but just a few… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 7700  to  14000 

*Rates Subject to Change

 

'SUNSET DREAMS @ FLORIDA BAY': Luxury 3BR/2BA Waterfront Condo by Marina... Vacation Condo Rental: 390180

'SUNSET DREAMS @ FLORIDA BAY': Luxury 3BR/2BA Waterfront Condo by Marina...

Description: 'Sunset Dreams' has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4000  to  8000 

*Rates Subject to Change

 

'CIELO TROPICALE @ CASA EAST': 4BR/4BA Pavilion-Style Home with Pool.. Vacation House Rental: 390181

'CIELO TROPICALE @ CASA EAST': 4BR/4BA Pavilion-Style Home with Pool..

Description: On a quiet street just a couple blocks from Old Town is 'Ceilo Tropicale', a stunning home completely hidden from view by large… More

Bedrooms: 4
Sleeps: 10

*Rates: monthly, From: 8000  to  16000 

*Rates Subject to Change

 

'SOUTHERN STAR' @ WILLIAM STREET' Historic 3BR/3BA Home with Pool... Vacation House Rental: 390182

'SOUTHERN STAR' @ WILLIAM STREET' Historic 3BR/3BA Home with Pool...

Description: Half a block from the Historic Seaport on William Street is a home that was recently recognized by the Historic Florida Key… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 6600  to  14000 

*Rates Subject to Change

 

'AZURE MORNING' @ OCEANSIDE MARINA': Lavish 3BR/2BA Oceanfront Condo w/Pool Vacation Condo Rental: 390183

'AZURE MORNING' @ OCEANSIDE MARINA': Lavish 3BR/2BA Oceanfront Condo w/Pool

Description: Imagine waking up every morning to the sun rising over the azure blue Atlantic Ocean. That's what you will experience with this… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 5000  to  9850 

*Rates Subject to Change

 

'THE CORAL HOUSE @ THE SEAPORT': Lush 4BR/3.5BA Private Home w/Pool & Spa... Vacation House Rental: 390184

'THE CORAL HOUSE @ THE SEAPORT': Lush 4BR/3.5BA Private Home w/Pool & Spa...

Description: 'The Coral House' is a historic home situated in the heart of Old Town, near the Historic Seaport. You'll be just steps from… More

Bedrooms: 4
Sleeps: 10

*Rates: monthly, From: 9000  to  16000 

*Rates Subject to Change

 

'SOUTHERNMOST BELLE @ THE ANNEX': Historic 7BR/5BA Home, Wide Porches & Pool Vacation House Rental: 390185

'SOUTHERNMOST BELLE @ THE ANNEX': Historic 7BR/5BA Home, Wide Porches & Pool

Description: 'Southernmost Belle' is unique among vacation homes in Key West. First of all, is the location: This lavish mansion is located at… More

Bedrooms: 7
Sleeps: 14

*Rates: monthly, From: 27000  to  45000 

*Rates Subject to Change

 

“FAT NANCY'S VILLA @ THE CLUB”: Bright & Airy 2BR/2BA Townhome near The Pool Vacation House Rental: 390186

“FAT NANCY'S VILLA @ THE CLUB”: Bright & Airy 2BR/2BA Townhome near The Pool

Description: “Fat Nancy's Villa” is a two-story town home located at the Key West Golf Club, just a block from the community's large resort style… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3500  to  5000 

*Rates Subject to Change

 

“CASA PARADISO @ THE CLUB': Elegant 2BR/1.5BA Home near Community Pool...... Vacation Villa Rental: 390187

“CASA PARADISO @ THE CLUB': Elegant 2BR/1.5BA Home near Community Pool......

Description: 'CasaParadiso' is an elegant two-story town home located at the Key West Golf Club, directly across the street from the community's… More

Bedrooms: 2
Sleeps: 5

*Rates: monthly, From: 2000  to  5000 

*Rates Subject to Change

 

'WATER'S EDGE @ GULFVIEW POINTE': Waterfront 4BR/2.5BA Home, Private Pool... Vacation House Rental: 390188

'WATER'S EDGE @ GULFVIEW POINTE': Waterfront 4BR/2.5BA Home, Private Pool...

Description: On the north shore of Key West is an exclusive gated community of 25 homes that sit on the former Monroe County Fairground. Gulfview… More

Bedrooms: 4
Sleeps: 10

*Rates: monthly, From: 5500  to  12000 

*Rates Subject to Change

 

'CONCH CASITA 3 @ ELIZABETH': Immaculate 2BR/1BA Conch Cottage in Old Town... Vacation Cottage Rental: 390189

'CONCH CASITA 3 @ ELIZABETH': Immaculate 2BR/1BA Conch Cottage in Old Town...

Description: You will never find this perfect little cottage (or its sister cottage, 'Conch Casita 2') without directions, even though it is… More

Bedrooms: 1
Sleeps: 4

*Rates: monthly, From: 2800  to  4800 

*Rates Subject to Change

 

'TROPICAL JEWEL @ ELIZABETH': 2BR/2BA Restored Conch Cottage @ The Seaport... Vacation House Rental: 390191

'TROPICAL JEWEL @ ELIZABETH': 2BR/2BA Restored Conch Cottage @ The Seaport...

Description: If ever a home was a precious jewel, it is this immaculate restoration located on 320 Elizabeth Street just two blocks from the… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 6000  to  10000 

*Rates Subject to Change

 

“MAISON TROPICALE @ FRANCES': Lush 3BR/3BA Old Town Home,Pool & Spa... Vacation House Rental: 390192

“MAISON TROPICALE @ FRANCES': Lush 3BR/3BA Old Town Home,Pool & Spa...

Description: Imagine a traditional conch home stunningly restored, then decorated in a post-modern style with vivid colors and sophisticated… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 7700  to  15000 

*Rates Subject to Change

 

“BONEFISH HIDEAWAY @ SUGARLOAF': 3BR 2BA Waterfront Home, Jacuzzi, 60’ Dock... Vacation House Rental: 390193

“BONEFISH HIDEAWAY @ SUGARLOAF': 3BR 2BA Waterfront Home, Jacuzzi, 60’ Dock...

Description: Located on the south side of Sugarloaf Key, “Bonefish Hideaway' is a home that is perfect for the family that wants to be away from… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4500  to  6000 

*Rates Subject to Change

 

'PORTSIDE MANSION @ THE SEAPORT': 6BR 6.5BA Compound @ Historic Seaport... Vacation House Rental: 390194

'PORTSIDE MANSION @ THE SEAPORT': 6BR 6.5BA Compound @ Historic Seaport...

Description: In the heart of Old Town, just a half block from the Historic Seaport Harbor, is a very exclusive and unique residence: Two homes… More

Bedrooms: 6
Sleeps: 12

*Rates: monthly, From: 16000  to  29000 

*Rates Subject to Change

 

'CASA FELIZ @ WHITE': Lushly Furnished 3BR/3.5BA Private Home in Old Town... Vacation House Rental: 390195

'CASA FELIZ @ WHITE': Lushly Furnished 3BR/3.5BA Private Home in Old Town...

Description: If you want to experience Key West at its historic best, Casa Feliz is the perfect choice for your stay. A wide porch graces the… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 6600  to  14000 

*Rates Subject to Change

 

“ANGEL CONCH @ ANGELA STREET': Heavenly 3BR/2.5BA Home with Pool & Jacuzzi... Vacation House Rental: 390197

“ANGEL CONCH @ ANGELA STREET': Heavenly 3BR/2.5BA Home with Pool & Jacuzzi...

Description: In a neighborhood with some of the nicest homes in town, this exquisitely detailed home on Angela Street stands out. As you come… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 6000  to  12000 

*Rates Subject to Change

 

'SUNSET DREAMS 2 @ FLORIDA BAY': Luxurious 2BR/2BA Waterfront Condo... Vacation Condo Rental: 390198

'SUNSET DREAMS 2 @ FLORIDA BAY': Luxurious 2BR/2BA Waterfront Condo...

Description: 'Sunset Dreams 2' has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2800  to  7700 

*Rates Subject to Change

 

'ARTIST'S GALLERY @ WHITE': Immacualte 2BR/2BA Condo near Higgs Beach... Vacation Condo Rental: 390199

'ARTIST'S GALLERY @ WHITE': Immacualte 2BR/2BA Condo near Higgs Beach...

Description: 'Artist's Gallery @ White' is the perfect place to stay if you want to really feel like a 'local'. Located in the heart of the White… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2800  to  4800 

*Rates Subject to Change

 

'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Historic Home with Large Pool Vacation House Rental: 390200

'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Historic Home with Large Pool

Description: 'Casa Blanca 1888' has everything you would want for your stay in Old Town Key West. Its central location in historic Old Town at… More

Bedrooms: 4
Sleeps: 10

*Rates: monthly, From: 8000  to  16000 

*Rates Subject to Change

 

“HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Home with Pool & Spa Vacation House Rental: 390201

“HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Home with Pool & Spa

Description: In the Historic Seaport area of Old Town, there is a house that is very attractive from the street, beautifully maintained with… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 8000  to  16000 

*Rates Subject to Change

 

“NOONA'S MANSION-by-the-SEA @ THE ANNEX' 7BR/5.5BA Home with Pool... Vacation House Rental: 390202

“NOONA'S MANSION-by-the-SEA @ THE ANNEX' 7BR/5.5BA Home with Pool...

Description: Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished… More

Bedrooms: 7
Sleeps: 14

*Rates: monthly, From: 27000  to  48000 

*Rates Subject to Change

 

'NATALIE'S BAHAMA CONCH' @ THE SANCTUARY': Lush 3BR/2.5BA Home, Pool... Vacation House Rental: 390203

'NATALIE'S BAHAMA CONCH' @ THE SANCTUARY': Lush 3BR/2.5BA Home, Pool...

Description: 'Natalie's Bahama Conch' is located in the Sanctuary at the Key West Golf Club. Just about everything in the house has been redone,… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 5000  to  9000 

*Rates Subject to Change

 

'LA PROVENCE @ THE SANCTUARY': 2 Master Suites, Spa Pool with Walled Yard... Vacation House Rental: 390204

'LA PROVENCE @ THE SANCTUARY': 2 Master Suites, Spa Pool with Walled Yard...

Description: 'La Provence' is a bright and airy private home located in The Sanctuary, a quiet gated enclave set within the already gated grounds… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3500  to  6900 

*Rates Subject to Change

 

'EDEN @ THE ANNEX': 2BR/1.5BA Luxury Townhom next to Mallory Square.. Vacation House Rental: 390205

'EDEN @ THE ANNEX': 2BR/1.5BA Luxury Townhom next to Mallory Square..

Description: 'Eden @ The Annex' is a charming townhome in Truman Annex, a gated community located in the very heart of Old Town Key West. You'll… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4800  to  8250 

*Rates Subject to Change

 

'KOI HOUSE @ UPTOWN KEY WEST': 5 BR/5BA Compound, Courtyard & Koi Pond & Pool Vacation House Rental: 390206

'KOI HOUSE @ UPTOWN KEY WEST': 5 BR/5BA Compound, Courtyard & Koi Pond & Pool

Description: Located on a quiet little cul-de-sac not far from the Southernmost Point in the Uptown part of Key West, you will find Koi House, a… More

Bedrooms: 5
Sleeps: 12

*Rates: monthly, From: 8800  to  19000 

*Rates Subject to Change

 

'POOLSIDE RETREAT @ THE POOL': Poolside Luxury Villa with 2 Master Suites... Vacation Villa Rental: 390207

'POOLSIDE RETREAT @ THE POOL': Poolside Luxury Villa with 2 Master Suites...

Description: Poolside Retreat is a private two-story villa nestled in the lush tropical landscaping that surrounds the gorgeous resort-style… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3300  to  5950 

*Rates Subject to Change

 

'PARADISE PERFECTED @ THE SANCTUARY': Elegant 3BR/2.5BA Luxury Home... Vacation House Rental: 390208

'PARADISE PERFECTED @ THE SANCTUARY': Elegant 3BR/2.5BA Luxury Home...

Description: Choosing a vacation home is always a challenge. It sometimes seems like the owners have decorated the home with the best that the… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 4000  to  9000 

*Rates Subject to Change

 

“PENTHOUSE @ THE STEAMPLANT': Luxurious 3BR/3.5BA Condo w/ Private Pool... Vacation Condo Rental: 390209

“PENTHOUSE @ THE STEAMPLANT': Luxurious 3BR/3.5BA Condo w/ Private Pool...

Description: There is nothing else like this home in all of Key West: Card-only access to your assigned spaces in the parking garage, a private… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 8000  to  15000 

*Rates Subject to Change

 

'FLAMINGO DREAMS @ GRINNELL': Pristine 3BR/2BA Conch Home in Old Town... Vacation House Rental: 390211

'FLAMINGO DREAMS @ GRINNELL': Pristine 3BR/2BA Conch Home in Old Town...

Description: In the heart of Old Town is a classic Conch House that has been completely renovated and updated while retaining all of its historic… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 4500  to  11000 

*Rates Subject to Change

 

'PARADISE @ THE BIGHT': Large 5BR/4BA Waterfront Home w/Private Dock... Vacation House Rental: 390212

'PARADISE @ THE BIGHT': Large 5BR/4BA Waterfront Home w/Private Dock...

Description: This beautiful 5 bedroom home is located directly on the water at Garrison Bight, with direct access to Florida Bay. 'Paradise @ The… More

Bedrooms: 5
Sleeps: 12

*Rates: monthly, From: 17500  to  26400 

*Rates Subject to Change

 

“VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex... Vacation Villa Rental: 390213

“VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...

Description: This beautiful townhome is to be found in the Truman Annex, Key West’s most exclusive gated community. You’ll be just around the… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 6000  to  8800 

*Rates Subject to Change

 

Key West 1800 Atlantic - The Grand Vista - 2 bedroom suite Vacation Condo Rental: 390410

Key West 1800 Atlantic - The Grand Vista - 2 bedroom suite

Description: 2 Bedroom 2 bath suite, Totally renovated with flat screen plasma TV"s in both bedrooms and the living room. All brand new furniture… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

1800 Atlantic Key West 2 bedroom Penthouse Vacation Condo Rental: 390411

1800 Atlantic Key West 2 bedroom Penthouse

Description: Great 2 Bedroom 2 bath ocean-view unit on the Top floor with a fantastic views along Smathers Beach. Enjoy the great ocean-breezes… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3500  to  6500 

*Rates Subject to Change

 

Old Town Key West 2 bedroom Cottage with Private Pool Vacation Cottage Rental: 390412

Old Town Key West 2 bedroom Cottage with Private Pool

Description: Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest.… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4500  to  4500 

*Rates Subject to Change

 

2 Bedroom Garden-View Condo at 1800 Atlantic Vacation Condo Rental: 390413

2 Bedroom Garden-View Condo at 1800 Atlantic

Description: Perfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Nassau Suite - Old Town Key West Villa Vacation Villa Rental: 390414

Nassau Suite - Old Town Key West Villa

Description: Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair,… More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 1050  to  1900 

*Rates Subject to Change

 

Little Palm Vacation Cottage Rental: 391119

Little Palm

Description: LITTLE PALM - What an idyllic setting! Picture a new cottage with all the must have's for a great Key West vacation - in a setting… More

Bedrooms: 0
Sleeps: 2

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Island Oasis Vacation House Rental: 391120

Island Oasis

Description: ISLAND OASIS: Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West Hideaway. A… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Treetop Island Treasure, Palm Isle, Just off Duval Vacation Apartment Rental: 391121

Treetop Island Treasure, Palm Isle, Just off Duval

Description: Palm Isle - a room ahead of its time - A truly "green unit". Your room mate or in this case "suite mate" is a giant Sapodilla tree… More

Bedrooms: 0
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

PET FRIENDLY COTTAGE Vacation Cottage Rental: 391123

PET FRIENDLY COTTAGE

Description: Charming cottage comes complete with a kitchenette packed with all the necessities for a great Key West vacation. Nothing's been… More

Bedrooms: 0
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Seaport Suite - WALK EVERYWHERE! Vacation Apartment Rental: 391124

Seaport Suite - WALK EVERYWHERE!

Description: Seaport Suite is available for daily rentals and is located on the second floor of the RE/MAX Southernmost building in Old Town, Key… More

Bedrooms: 4
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Downtown Key West Pool Home Vacation House Rental: 391125

Downtown Key West Pool Home

Description: Jimmy Buffett) stayed at Havana Hideaway and wrote the song Kokomo - according to a very reliable source at the Pink Cab Company!… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Absolutely Paradise Vacation House Rental: 391126

Absolutely Paradise

Description: Located in Old Town Key West tucked off of Simonton Street lies a beautiful home that will entice, entertain, and excite the… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Poolside Paradise Vacation Cottage Rental: 391127

Poolside Paradise

Description: Where else can you find resort style accommodations at motel pricing? Poolside Paradise, one of our most popular properties,… More

Bedrooms: 1
Sleeps: 2

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Southern Cross Vacation House Rental: 391128

Southern Cross

Description: Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Tropical Retreat Vacation Cottage Rental: 391129

Tropical Retreat

Description: Lush gardens surround this lovingly restored two-story Bahamian house. This upstairs suite has two bedrooms each featuring a queen… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Tropical Village Cottage Vacation Cottage Rental: 391130

Tropical Village Cottage

Description: Tropical Village Cottage - is the epitome of modern Key West. This two bedroom, two bath conch cottage overlooks a shared… More

Bedrooms: 2
Sleeps: 5

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Toon Hall Vacation House Rental: 391131

Toon Hall

Description: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning… More

Bedrooms: 3
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Key West Cottage: Bahama House, Key West, FL, 33040 Vacation Cottage Rental: 391132

Key West Cottage: Bahama House, Key West, FL, 33040

Description: The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch cottage. It is a perfect example of… More

Bedrooms: 2
Sleeps: 6

*Rates: extra-night, From: 298  to  298 

*Rates Subject to Change

 

Tropical Hideaway Vacation Cottage Rental: 391133

Tropical Hideaway

Description: Lush gardens surround this lovingly restored two-story Bahamian house. This downstairs suite has one bedrooms with full bath and… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Key West Hidaway Vacation House Rental: 391134

Key West Hidaway

Description: Key West Hideaway: As you approach the front door to 1120 Curry Lane the transformation starts to happen. The small lush tropical… More

Bedrooms: 3
Sleeps: 10

*Rates: monthly, From: 5000  to  7500 

*Rates Subject to Change

 

The Hidden Treasure in old town. Walk to the beach! Vacation Studio Rental: 392129

The Hidden Treasure in old town. Walk to the beach!

Description: Centrally located, our Studio apartment is walking or cycling distance to beaches, shops and entertainment. The studio suit with… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 2500  to  3000 

*Rates Subject to Change

 

$185 A Day Stay Above the Sea 3BR/3BA cool A/C full kitchen large livingroom Vacation Yacht Rental: 392751

$185 A Day Stay Above the Sea 3BR/3BA cool A/C full kitchen large livingroom

Description: Why stay in a boring expensive hotel, this is the best deal in Key West. Have your own private yacht with 3 bedrooms and 3 baths,… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 1295  to  1295 

*Rates Subject to Change

 

Heron's Nest ~ Old Town Condo with treetop views near the Historic Seaport Vacation Condo Rental: 393344

Heron's Nest ~ Old Town Condo with treetop views near the Historic Seaport

Description: Hidden away yet in the middle of it all! Cute & comfortable 2nd story condo perfect for getting away from the cold northern winters.… More

Bedrooms: 2
Sleeps: 5

*Rates: monthly, From: 2500  to  4500 

*Rates Subject to Change

 

CARIBBEAN SOUL ~ Clean, Spacious & Central Vacation … Rental: 395078

CARIBBEAN SOUL ~ Clean, Spacious & Central

Description: Quintessential Key West vacation home leaving nothing more to be desired. Framed by a white picket fence you will be welcomed to… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 5000  to  9000 

*Rates Subject to Change

 

Island Couture ~ Luxury retreat by local Artist with stunning outdoor space Vacation House Rental: 395081

Island Couture ~ Luxury retreat by local Artist with stunning outdoor space

Description: Irresistable & artful 1940's home renovated & decorated by artist Deborah Yates. This is a unique opporuntunity to experiance the… More

Bedrooms: 3
Sleeps: 7

*Rates: monthly, From: 6000  to  9000 

*Rates Subject to Change

 

Double Dutch Vacation House Rental: 395082

Double Dutch

Description: Classic Old Town Key West home boasting rare combination of LOCATION, CHARACTER & SPACE. A meticulous restoration of historic… More

Bedrooms: 4
Sleeps: 10

*Rates: monthly, From: 8500  to  14000 

*Rates Subject to Change

 

The Golden Heron Vacation House Rental: 399320

The Golden Heron

Description: The Key West Golden Heron is a Gold Star Landmark home, walking distance to the beaches, shopping and famous Duval Street, yet… More

Bedrooms: 5
Sleeps: 12

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Canal Front (Deep Water) Tropical Villa Vacation House Rental: 399608

Canal Front (Deep Water) Tropical Villa

Description: Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in Summerland… More

Bedrooms: 2
Sleeps: 8

*Rates: monthly, From: 3000  to  5000 

*Rates Subject to Change

 

Best Value! Beautiful, Waterfront Vacation Home. Vacation House Rental: 399780

Best Value! Beautiful, Waterfront Vacation Home.

Description: Your dream vacation awaits you at this beautiful 2 bedroom, 2 bath waterfront vacation home. This Key West style home features a 35'… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 165  to  165 

*Rates Subject to Change

 

Duval Sea Turtle Vacation House Rental: 40019

Duval Sea Turtle

Description: DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 30  to  435 

*Rates Subject to Change

 

Duval Courtyard Vacation House Rental: 40020

Duval Courtyard

Description: DUVAL COURTYARD - Located just steps from famous Duval Street in the rooftop community of Duval Square, this recently renovated… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 100  to  822.5 

*Rates Subject to Change

 

Caribbean Duval Vacation House Rental: 40022

Caribbean Duval

Description: Nestled above Duval St. in the heart of the Art district, in Duval Square, is this lovely 2 bedroom, 2.5 bath townhouse, “Caribbean… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 75  to  435 

*Rates Subject to Change

 

Brisa del Mar Vacation Condo Rental: 40033

Brisa del Mar

Description: BRISA DEL MAR - This two bedroom, two bath condominium is located ocean front in a gated community with a spectacular view of the… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 85  to  434 

*Rates Subject to Change

 

The Hemingway Vacation House Rental: 40039

The Hemingway

Description: THE HEMINGWAY -- A beautiful two bedroom two bath townhome located in the private, gated community of Truman Annex. An ideal… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 200  to  2610 

*Rates Subject to Change

 

Parrot Perch Vacation Condo Rental: 40042

Parrot Perch

Description: PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex. This property is in a great location and a… More

Bedrooms: 2
Sleeps: 5

*Rates: weekly, From: 500  to  2320 

*Rates Subject to Change

 

Surf Side Vacation Condo Rental: 40052

Surf Side

Description: SURF SIDE - Search no further! This fabulous condominium is directly on the Atlantic Ocean. Located at the end of the building… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 145  to  650 

*Rates Subject to Change

 

Coral Caribe Vacation House Rental: 40061

Coral Caribe

Description: CORAL CARIBE in the Coral Hammock Community. 2 bedroom 2.5 bath shared pool with off street parking. A gated entry, lushly… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 70  to  275 

*Rates Subject to Change

 

Bahamian Reed Vacation House Rental: 40062

Bahamian Reed

Description: Bahamian Reed is a luxury townhome located in the prestigious community of Truman Annex. This property is conveniently located just… More

Bedrooms: 2
Sleeps: 5

*Rates: weekly, From: 500  to  2610 

*Rates Subject to Change

 

Key West Ginger House Vacation House Rental: 40063

Key West Ginger House

Description: KEY WEST GINGER HOUSE - An absolute jewel a few doors from Duval Street. This single family home is named for the breathtaking… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 75  to  413.25 

*Rates Subject to Change

 

Crowner's Jewel Vacation House Rental: 40065

Crowner's Jewel

Description: CROWNER'S JEWEL at the Truman Annex. Experience the finest in Key West living when you stay in this delightful two bedroom two and… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 200  to  2900 

*Rates Subject to Change

 

A Place in Paradise Vacation House Rental: 40067

A Place in Paradise

Description: A Place in Paradise - You will experience true Key West living when you stay in this delightful two bedroom two and one half bath… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 500  to  2900 

*Rates Subject to Change

 

Island Pearl Vacation House Rental: 40068

Island Pearl

Description: ISLAND PEARL -- True island living in this 1 loft bedroom 1 bath cottage located in the heart of Old Town Key West. French doors… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 60  to  391.5 

*Rates Subject to Change

 

Leeward Isle Key West Retreat Vacation House Rental: 40071

Leeward Isle Key West Retreat

Description: LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private parking lot you know you are some… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 75  to  435 

*Rates Subject to Change

 

Southern Wind Vacation House Rental: 40073

Southern Wind

Description: SOUTHERN WIND -- A renovated two bedroom two bath two story home located in the Windward Park compound in the heart of Old Town and… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 75  to  435 

*Rates Subject to Change

 

Egret Cottage Vacation House Rental: 40076

Egret Cottage

Description: EGRET COTTAGE -- The Colony Suites is a charming compound nestled in the heart of Historic Old Town Key West, just three blocks from… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 75  to  384.25 

*Rates Subject to Change

 

On a Deep Water Canal with Open Water Views! - A Gift From the Sea Vacation House Rental: 407393

On a Deep Water Canal with Open Water Views! - A Gift From the Sea

Description: “If you surrender completely to the moments as they pass, you live more richly those moments.” – Anne Morrow Lindbergh A Gift from… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3600  to  3600 

*Rates Subject to Change

 

Quaint Houseboat with wet bar and awesome views - Key West Fishing Vacation Vacation Boat Rental: 411266

Quaint Houseboat with wet bar and awesome views - Key West Fishing Vacation

Description: This charming two bedroom, two bath houseboat is permanently docked at beautiful Sunset Marina in Key West. Just minutes from the… More

Bedrooms: 2
Sleeps: 5

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Charming beach front cottages on offshore Island Vacation Cottage Rental: 412562

Charming beach front cottages on offshore Island

Description: The Captains House is the original house on the 67 acre island settled by Captain Percy Cook in 1923. Cooks Island is a rustic idyll… More

Bedrooms: 3
Sleeps: 5

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

'Sunset Vista' 2 BR/2 BA Canalfront home. Family fun and fisherman's dream! Vacation House Rental: 441340

'Sunset Vista' 2 BR/2 BA Canalfront home. Family fun and fisherman's dream!

Description: 'Sunset Vista' is a completely updated canal front home located just 4 lots from open water in prestigious Pine Channel Estates. See… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3600  to  3600 

*Rates Subject to Change

 

Villa Paradiso a Peaceful Private Retreat Vacation Villa Rental: 489605

Villa Paradiso a Peaceful Private Retreat

Description: Located in a quiet, tranquil and charming residential area, 4 blocks (5-10 min walk) from the beaches on the south of the island,… More

Bedrooms: 3
Sleeps: 6

*Rates: extra-night, From: 360  to  730 

*Rates Subject to Change

 

Villa Tropicale Vacation House Rental: 56462

Villa Tropicale

Description: Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private… More

Bedrooms: 4
Sleeps: 8

*Rates: nightly-weekday, From: 710  to  1220 

*Rates Subject to Change

 

Casa Margarita Vacation House Rental: 56463

Casa Margarita

Description: Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And the historic seaport… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 430  to  650 

*Rates Subject to Change

 

Shipyard Palms Vacation Condo Rental: 56466

Shipyard Palms

Description: In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard Condominium… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 170  to  340 

*Rates Subject to Change

 

Shipyard Splendor Vacation Condo Rental: 56467

Shipyard Splendor

Description: A lovely condominium located in the Truman Annex Shipyard Condominiums. Location is everything to be walking distance to Fort… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 170  to  340 

*Rates Subject to Change

 

Vista Fresco Vacation Condo Rental: 7013304

Vista Fresco

Description: Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 210  to  380 

*Rates Subject to Change

 

Nautical Dreams Vacation House Rental: 7013689

Nautical Dreams

Description: NAUTICAL DREAMS -- Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2 bedroom home, located in a… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2500  to  5300 

*Rates Subject to Change

 

Island Spice Vacation House Rental: 7013690

Island Spice

Description: ISLAND SPICE -- A lovely 2 bedroom, 2.5 bath townhome, located in the historic Foundry building of the prestigious Truman Annex… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 600  to  3190 

*Rates Subject to Change

 

Verandah Vacation House Rental: 7013694

Verandah

Description: VERANDAH - Tucked away on historic Frances Street lies your island escape… Verandah is a stunning two bedroom two bath home with a… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2800  to  6300 

*Rates Subject to Change

 

South St. Cottage Vacation House Rental: 7028681

South St. Cottage

Description: A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 3200  to  6500 

*Rates Subject to Change

 

Pete's Cottages Vacation House Rental: 7028682

Pete's Cottages

Description: This property has it all! This award winning renovation offers the styling of the original shot gun homes of Key West restored with… More

Bedrooms: 4
Sleeps: 8

*Rates: nightly-weekday, From: 530  to  1450 

*Rates Subject to Change

 

La Brisa #306E Tropical Tuscany Vacation Condo Rental: 7028683

La Brisa #306E Tropical Tuscany

Description: La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  370 

*Rates Subject to Change

 

Florida Palm Vacation Condo Rental: 7028686

Florida Palm

Description: ~~~~~ WAIT A MINUTE - 50% OFF Any new arrival thru October 1, 2011~~~~~ Call today to reserve your vacation in Key West~~~~~ FLORIDA… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 30  to  368.75 

*Rates Subject to Change

 

The Loft at Echo Gardens Vacation Condo Rental: 7030622

The Loft at Echo Gardens

Description: Looking for the perfect Key West get away or corporate retreat? Look no further, here is your opportunity. This little gem is… More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 816.69  to  816.69 

*Rates Subject to Change

 

BMW Fantasy Vacation Condo Rental: 7030623

BMW Fantasy

Description: Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 175  to  250 

*Rates Subject to Change

 

Garden Villa Vacation Condo Rental: 7030624

Garden Villa

Description: A delightful, deluxe one bedroom condo unit in the beautiful Southard Square complex. There's a king size bed in the bedroom and a… More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 816.69  to  816.69 

*Rates Subject to Change

 

Ocean Paradise Vacation Condo Rental: 7030625

Ocean Paradise

Description: 3-night minimum rental. Marvel at the topaz Caribbean view through every window of your vacation paradise at King's Pointe’s… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 175  to  250 

*Rates Subject to Change

 

Shipyard 253 Vacation Condo Rental: 7030626

Shipyard 253

Description: It is an upstairs unti with 2 bedrooms and 1 Bathroom with 1 queen, 2 twins and 1 pullout sofa. There is a balcony on the front and… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1200  to  1500 

*Rates Subject to Change

 

William Street House Vacation House Rental: 7030627

William Street House

Description: Located in Old Town, This home is conveniently located within walking distance to the Seaport, restaurants, and major attractions.… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1516.69  to  1516.69 

*Rates Subject to Change

 

Seaport House Vacation House Rental: 7030631

Seaport House

Description: Located in Old Town, this home is conveniently located within walking distance to the Seaport, restaurants, and major attractions.… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1050  to  1050 

*Rates Subject to Change

 

Shipyard 106-2 Vacation Condo Rental: 7030632

Shipyard 106-2

Description: Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a… More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 1000  to  1500 

*Rates Subject to Change

 

Seaside 33 Vacation Condo Rental: 7030633

Seaside 33

Description: Luxury three level town home in a gated community. The home features 2 master suites, 3 full baths, large rooms, vaulted ceilings,… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1127  to  1127 

*Rates Subject to Change

 

Coral Hammock 36 Vacation Condo Rental: 7030634

Coral Hammock 36

Description: Coral Hammock is one of the newest gated communities with 55 luxury resort homes with a lavish Clubhouse, Pool and lushly landscaped… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 175  to  175 

*Rates Subject to Change

 

The Palms Vacation House Rental: 7030636

The Palms

Description: Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 1283.31  to  1283.31 

*Rates Subject to Change

 

The Pearl in Paradise Vacation House Rental: 7030638

The Pearl in Paradise

Description: Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district.… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1166.69  to  1166.69 

*Rates Subject to Change

 

Eaton Manor Vacation Condo Rental: 7030640

Eaton Manor

Description: Eaton Manor sits on the north side of LaBrisa and provides easy access to Smathers beach, where you can sail, boat, kiteboard,… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1250  to  1750 

*Rates Subject to Change

 

Coral Hammock 34 Vacation Condo Rental: 7030641

Coral Hammock 34

Description: Coral Hammock is one of the newest gated communities with 55 luxury resort homes with a lavish Clubhouse, Pool and lushly landscaped… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 175  to  175 

*Rates Subject to Change

 

205E La Brisa Vacation Condo Rental: 7030644

205E La Brisa

Description: Bright, tropical colors and tile floors provide an island ambience to this two bedroom, two bathroom ocean view condominium. The… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1575  to  1750 

*Rates Subject to Change

 

Boater's Dream Vacation Condo Rental: 7030646

Boater's Dream

Description: Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1061.69  to  1061.69 

*Rates Subject to Change

 

Tropical Hideaway Vacation House Rental: 7030648

Tropical Hideaway

Description: Three bedroom, two bath home with private pool on a canal in Key West! Have all the benefits of being "on the keys". Enjoy water… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 1283.31  to  1283.31 

*Rates Subject to Change

 

Casa Del Aquabella Vacation House Rental: 7031376

Casa Del Aquabella

Description: Art Deco Dream! Key Haven, open water views & canal front home. Totally private on two lots, this unique ground level masterpiece… More

Bedrooms: 4
Sleeps: 10

*Rates: weekly, From: 2450  to  2450 

*Rates Subject to Change

 

Manatee Manor Vacation House Rental: 7031419

Manatee Manor

Description: Close to Old Town, and yet a world Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 1166.69  to  1166.69 

*Rates Subject to Change

 

RVLOT 070 Spanish Main Vacation House Rental: 7034309

RVLOT 070 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 200  to  490 

*Rates Subject to Change

 

RVLOT 124 Spanish Main Vacation House Rental: 7034310

RVLOT 124 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 476  to  595 

*Rates Subject to Change

 

RVLOT 178 Spanish Main Vacation House Rental: 7034312

RVLOT 178 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 420  to  525 

*Rates Subject to Change

 

RVLOT 285 Spanish Main Vacation House Rental: 7034313

RVLOT 285 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 420  to  525 

*Rates Subject to Change

 

RVLOT 290 Spanish Main Vacation House Rental: 7034314

RVLOT 290 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 420  to  525 

*Rates Subject to Change

 

RVLOT 303 Spanish Main Vacation House Rental: 7034315

RVLOT 303 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 525  to  595 

*Rates Subject to Change

 

RVLOT 304 Spanish Main Vacation House Rental: 7034316

RVLOT 304 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 525  to  595 

*Rates Subject to Change

 

RVLOT 305 Spanish Main Vacation House Rental: 7034317

RVLOT 305 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 448  to  560 

*Rates Subject to Change

 

RVLOT 307 Spanish Main Vacation House Rental: 7034318

RVLOT 307 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 280  to  420 

*Rates Subject to Change

 

RVLOT 358 Spanish Main Vacation House Rental: 7034322

RVLOT 358 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 420  to  525 

*Rates Subject to Change

 

RVLOT 377 Spanish Main Vacation House Rental: 7034323

RVLOT 377 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes More

Bedrooms: 0
Sleeps: 2

*Rates: weekly, From: 448  to  560 

*Rates Subject to Change

 

RVLOT 378 Spanish Main Vacation House Rental: 7034324

RVLOT 378 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 2

*Rates: weekly, From: 448  to  560 

*Rates Subject to Change

 

RVLOT 433 Spanish Main Vacation House Rental: 7034325

RVLOT 433 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 420  to  525 

*Rates Subject to Change

 

RVLOT 464 Spanish Main Vacation House Rental: 7034326

RVLOT 464 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 0

*Rates: weekly, From: 450  to  625 

*Rates Subject to Change

 

RVLOT 471 Spanish Main Vacation House Rental: 7034327

RVLOT 471 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Ocean/Bay Front: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 500  to  595 

*Rates Subject to Change

 

RVLOT 509 Spanish Main Vacation House Rental: 7034329

RVLOT 509 Spanish Main

Description: Turnday: Any. Amenities: Dockage, Smoking OK, Pets OK, Pool, Hot Tub/Jacuzzi, Trailer Parking. More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 300  to  540 

*Rates Subject to Change

 

RVLOT 564 Spanish Main Vacation House Rental: 7034331

RVLOT 564 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 476  to  595 

*Rates Subject to Change

 

RVLOT 581 Spanish Main Vacation House Rental: 7034332

RVLOT 581 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 476  to  595 

*Rates Subject to Change

 

RVLOT 588 Spanish Main Vacation House Rental: 7034333

RVLOT 588 Spanish Main

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 476  to  595 

*Rates Subject to Change

 

RVLOT 612 Spanish Main Vacation House Rental: 7034334

RVLOT 612 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 392  to  420 

*Rates Subject to Change

 

RVLOT 636 Spanish Main Vacation House Rental: 7034335

RVLOT 636 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 392  to  490 

*Rates Subject to Change

 

RVLOT 647 Spanish Main Vacation House Rental: 7034336

RVLOT 647 Spanish Main

Description: Turnday: Any. Amenities: Internet: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 0
Sleeps: 6

*Rates: weekly, From: 392  to  490 

*Rates Subject to Change

 

VO061 Vacation House Rental: 7034339

VO061

Description: Turnday: Any. Amenities: Pool: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 840  to  1150 

*Rates Subject to Change

 

VO089 Vacation House Rental: 7034340

VO089

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1000  to  1350 

*Rates Subject to Change

 

VO108 Vacation House Rental: 7034341

VO108

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 5

*Rates: weekly, From: 520  to  750 

*Rates Subject to Change

 

VO128 Vacation House Rental: 7034342

VO128

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 800  to  1200 

*Rates Subject to Change

 

VO130 Vacation House Rental: 7034343

VO130

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 880  to  1200 

*Rates Subject to Change

 

VO182 Vacation House Rental: 7034345

VO182

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Porch/Patio: Yes More

Bedrooms: 1
Sleeps: 6

*Rates: weekly, From: 750  to  899 

*Rates Subject to Change

 

VO184 Vacation House Rental: 7034346

VO184

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 600  to  850 

*Rates Subject to Change

 

VO192 Vacation House Rental: 7034348

VO192

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes Pets OK: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 840  to  1150 

*Rates Subject to Change

 

VO197 Vacation House Rental: 7034350

VO197

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1100  to  1460 

*Rates Subject to Change

 

VO215 Vacation House Rental: 7034352

VO215

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1000  to  1350 

*Rates Subject to Change

 

VO223 Vacation House Rental: 7034354

VO223

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 700  to  1350 

*Rates Subject to Change

 

VO238 Vacation House Rental: 7034356

VO238

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Pets OK: Yes More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 550  to  850 

*Rates Subject to Change

 

VO243 Vacation House Rental: 7034359

VO243

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Porch/Patio: Yes More

Bedrooms: 1
Sleeps: 6

*Rates: weekly, From: 750  to  850 

*Rates Subject to Change

 

VO264 Vacation House Rental: 7034361

VO264

Description: Turnday: Any. Amenities: Dockage: Yes Ocean/Bay Front: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1400  to  1850 

*Rates Subject to Change

 

VO274 Vacation House Rental: 7034363

VO274

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 895  to  1350 

*Rates Subject to Change

 

VO324 Vacation House Rental: 7034369

VO324

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Pets OK: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 600  to  1050 

*Rates Subject to Change

 

VO339 Vacation House Rental: 7034371

VO339

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes Pets OK: Yes More

Bedrooms: 1
Sleeps: 6

*Rates: weekly, From: 560  to  900 

*Rates Subject to Change

 

VO364 Vacation House Rental: 7034372

VO364

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1000  to  1400 

*Rates Subject to Change

 

VO367 Vacation House Rental: 7034374

VO367

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1000  to  1350 

*Rates Subject to Change

 

VO376 Vacation House Rental: 7034375

VO376

Description: Turnday: Any. Amenities: Dockage: Yes Ocean/Bay Front: Yes Pool: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 708  to  985 

*Rates Subject to Change

 

VO379 Vacation House Rental: 7034377

VO379

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 740  to  1025 

*Rates Subject to Change

 

VO385 Vacation House Rental: 7034379

VO385

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1080  to  1450 

*Rates Subject to Change

 

VO389 Vacation House Rental: 7034381

VO389

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1350  to  1500 

*Rates Subject to Change

 

VO420 Vacation House Rental: 7034385

VO420

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 708  to  985 

*Rates Subject to Change

 

VO424 Vacation House Rental: 7034387

VO424

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 725  to  1100 

*Rates Subject to Change

 

VO430 Vacation House Rental: 7034389

VO430

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 628  to  935 

*Rates Subject to Change

 

VO448 Vacation House Rental: 7034394

VO448

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 840  to  1150 

*Rates Subject to Change

 

VO449 Vacation House Rental: 7034395

VO449

Description: Canal Front Dockage - 71 feet Boat Whips & Cleats Bait Table Fresh water hose - dock Electric at dock Central A/C Ceiling Fans - all… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1000  to  1350 

*Rates Subject to Change

 

VO461 Vacation House Rental: 7034397

VO461

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 750  to  1250 

*Rates Subject to Change

 

VO468 Vacation House Rental: 7034399

VO468

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 960  to  1300 

*Rates Subject to Change

 

VO479 Vacation House Rental: 7034401

VO479

Description: Turnday: Any. Amenities: Dockage: Yes Ocean/Bay Front: Yes Internet: Yes Pool: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1200  to  1500 

*Rates Subject to Change

 

VO484 Vacation House Rental: 7034404

VO484

Description: Turnday: Any. Amenities: Dockage: Yes Ocean/Bay Front: Yes Pool: Yes Porch/Patio: Yes Pets OK: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 800  to  1200 

*Rates Subject to Change

 

VO517 Vacation House Rental: 7034408

VO517

Description: Turnday: Any. Amenities: Dockage: Yes Ocean/Bay Front: Yes Pool: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 800  to  1100 

*Rates Subject to Change

 

VO597 Vacation House Rental: 7034416

VO597

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 840  to  1150 

*Rates Subject to Change

 

VO606 Vacation House Rental: 7034418

VO606

Description: Turnday: Any. Amenities: Dockage: Yes Internet: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1100  to  1400 

*Rates Subject to Change

 

VO642 Vacation House Rental: 7034420

VO642

Description: Turnday: Any. Amenities: Pool: Yes Ice Maker: Yes Pets OK: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 700  to  900 

*Rates Subject to Change

 

VO644 Vacation House Rental: 7034422

VO644

Description: Turnday: Any. Amenities: Pool: Yes Ice Maker: Yes Pets OK: Yes More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 550  to  650 

*Rates Subject to Change

 

VO651 Vacation House Rental: 7034423

VO651

Description: Turnday: Any. Amenities: Pool: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 560  to  900 

*Rates Subject to Change

 

Casa Monte Vacation House Rental: 7034715

Casa Monte

Description: Ocean front masterpiece for those who want the very best for their vacation home. This multimillion dollar home boasts 4 bedrooms… More

Bedrooms: 4
Sleeps: 8

*Rates: monthly, From: 6900  to  7900 

*Rates Subject to Change

 

Our Island Thing Vacation House Rental: 7034889

Our Island Thing

Description: You'll feel right at home in this 3 bedroom, 2 bath home in Doctor's Arm on Big Pine Key. With a large recreation room for the whole… More

Bedrooms: 4
Sleeps: 9

*Rates: monthly, From: 3500  to  3750 

*Rates Subject to Change

 

Papaya Place Vacation Condo Rental: 7038978

Papaya Place

Description: PAPAYA PLACE pops with color! This great two bedroom two bath condominium at 1800 Atlantic Condominiums offers you a wonderful… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 70  to  531.25 

*Rates Subject to Change

 

At Home Key West Vacation Condo Rental: 7038980

At Home Key West

Description: BEACH HOUSE CONDO – Is a beautiful two bedroom two bath Shipyard condominium with a private Jacuzzi on the back patio. Located in… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 500  to  2610 

*Rates Subject to Change

 

Shipyard 210 - 4 Vacation House Rental: 7042520

Shipyard 210 - 4

Description: The first floor includes a front porch, bedroom, completely remodeled kitchen, remodeled lower bathroom, large open living area, and… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2200  to  3500 

*Rates Subject to Change

 

Conch Wind Vacation House Rental: 7056460

Conch Wind

Description: CONCH WIND - Stop searching,Conch Wind is the property you have been hunting for ! This two story Conch style townhome located in… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 75  to  435 

*Rates Subject to Change

 

Osprey Vacation Condo Rental: 7056462

Osprey

Description: OSPREY - This property is located in the same small community once was known as The Colony Suites, a charming and secluded Key West… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 90  to  250 

*Rates Subject to Change

 

Pelican Landing Bonaire Suite Vacation Condo Rental: 7067235

Pelican Landing Bonaire Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican Landing Bonaire Retreat Vacation Condo Rental: 7067236

Pelican Landing Bonaire Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Andros Retreat Vacation Condo Rental: 7067238

Pelican Landing Andros Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Aruba Retreat Vacation Condo Rental: 7067239

Pelican Landing Aruba Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Dominica Retreat Vacation Condo Rental: 7067240

Pelican Landing Dominica Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing St. Thomas Retreat Vacation Condo Rental: 7067241

Pelican Landing St. Thomas Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 4
Sleeps: 14

*Rates: nightly-weekday, From: 450  to  550 

*Rates Subject to Change

 

Pelican Landing Bermuda Retreat Vacation Condo Rental: 7067242

Pelican Landing Bermuda Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Aruba Suite Vacation Condo Rental: 7067243

Pelican Landing Aruba Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican Landing Aruba Room Vacation Condo Rental: 7067244

Pelican Landing Aruba Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Bonaire Room Vacation Condo Rental: 7067245

Pelican Landing Bonaire Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Dominica Room Vacation Condo Rental: 7067247

Pelican Landing Dominica Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Andros Suite Vacation Condo Rental: 7067248

Pelican Landing Andros Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican Landing Andros Room Vacation Condo Rental: 7067249

Pelican Landing Andros Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Bermuda Suite Vacation Condo Rental: 7067250

Pelican Landing Bermuda Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican Landing Bermuda Room Vacation Condo Rental: 7067251

Pelican Landing Bermuda Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Eleuthera Retreat Vacation Condo Rental: 7067978

Pelican Landing Eleuthera Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Curacao Retreat Vacation Condo Rental: 7067979

Pelican Landing Curacao Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing St. Kitts Retreat Vacation Condo Rental: 7067980

Pelican Landing St. Kitts Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 3
Sleeps: 10

*Rates: nightly-weekday, From: 350  to  450 

*Rates Subject to Change

 

Pelican Landing St.John Retreat Vacation Condo Rental: 7067981

Pelican Landing St.John Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 3
Sleeps: 10

*Rates: nightly-weekday, From: 350  to  450 

*Rates Subject to Change

 

Pelican Landing Flamingo Retreat Vacation Condo Rental: 7067982

Pelican Landing Flamingo Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Curacao Suite Vacation Condo Rental: 7067983

Pelican Landing Curacao Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican landing Eleuthera Suite Vacation Condo Rental: 7067984

Pelican landing Eleuthera Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican landing Eleuthera Room Vacation Condo Rental: 7067985

Pelican landing Eleuthera Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Flamingo Room Vacation Condo Rental: 7067986

Pelican Landing Flamingo Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Flamingo Suite Vacation Condo Rental: 7067992

Pelican Landing Flamingo Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican Landing Florida Retreat Vacation Condo Rental: 7069301

Pelican Landing Florida Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Antigua Retreat Vacation Condo Rental: 7069302

Pelican Landing Antigua Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 2
Sleeps: 8

*Rates: nightly-weekday, From: 250  to  350 

*Rates Subject to Change

 

Pelican Landing Antigua Suite Vacation Condo Rental: 7069303

Pelican Landing Antigua Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican Landing Florida Suite Vacation Condo Rental: 7069308

Pelican Landing Florida Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Pelican Landing Florida Room Vacation Condo Rental: 7069309

Pelican Landing Florida Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing St.Croix Retreat Vacation Condo Rental: 7069341

Pelican Landing St.Croix Retreat

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 4
Sleeps: 12

*Rates: nightly-weekday, From: 450  to  550 

*Rates Subject to Change

 

Cudjoe key's Perfect Getaway Vacation House Rental: 7073245

Cudjoe key's Perfect Getaway

Description: Located in a great neighborhood at 1032 Spanish Main, this home is perfect for your next vacation. This very clean and neat 3… More

Bedrooms: 3
Sleeps: 7

*Rates: weekly, From: 2500  to  2500 

*Rates Subject to Change

 

Summerland Dreamscape Vacation House Rental: 7073286

Summerland Dreamscape

Description: Our newly renovated 4100+ square foot house has 6 bedrooms 4.5 bathrooms houses situated on open water on Summerland Key. This… More

Bedrooms: 6
Sleeps: 1

*Rates: monthly, From: 20000  to  28000 

*Rates Subject to Change

 

Summerland Supreme Vacation House Rental: 7073895

Summerland Supreme

Description: Unique estate property that has it all. Dockage, sandy beach, shopping, scuba diving, off shore fishing, back country tarpon… More

Bedrooms: 7
Sleeps: 14

*Rates: monthly, From: 15000  to  23000 

*Rates Subject to Change

 

Dreaming On Duval Vacation House Rental: 7074434

Dreaming On Duval

Description: There's a new place on Duval Street in historic Key West and it is unique! Dreaming On Duval premieres in early 2010 as the most… More

Bedrooms: 5
Sleeps: 10

*Rates: nightly-weekday, From: 870  to  2000 

*Rates Subject to Change

 

Paradise Harbor Retreat Vacation House Rental: 7074435

Paradise Harbor Retreat

Description: Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 395  to  745 

*Rates Subject to Change

 

Beach Club #104 Vacation Condo Rental: 7074436

Beach Club #104

Description: Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 330  to  480 

*Rates Subject to Change

 

Old Town Beauty Vacation House Rental: 7074501

Old Town Beauty

Description: Wonderful Old town 3 bedroom, 2 full bath home in sunny paradise . It has off street parking, outdoor shower, shared heated pool… More

Bedrooms: 3
Sleeps: 1

*Rates: monthly, From: 6500  to  9000 

*Rates Subject to Change

 

Egret Landing Vacation Condo Rental: 7074503

Egret Landing

Description: Relax in Key West in This Beautiful Condo by the Sea This 2,000-square ft-condo is unique in that it has two large master bedroom… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 3950  to  3950 

*Rates Subject to Change

 

Key West Spectacular Vacation House Rental: 7074504

Key West Spectacular

Description: Our beautiful home is located on the bayside in Big Coppitt Key. Wake up in the morning to stunning views of the bay. The house is… More

Bedrooms: 5
Sleeps: 12

*Rates: weekly, From: 3000  to  5500 

*Rates Subject to Change

 

Pelican Landing Curacao Room Vacation Condo Rental: 7081777

Pelican Landing Curacao Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Dominica Suite Vacation Condo Rental: 7081778

Pelican Landing Dominica Suite

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 200  to  300 

*Rates Subject to Change

 

Key West Cottage Vacation Condo Rental: 7082006

Key West Cottage

Description: Location: Other Key West Properties, Key West, Key West Area, Florida Keys, Florida, USA (Downtown Key West-1 Block from Duval)… More

Bedrooms: 4
Sleeps: 10

*Rates: weekly, From: 6500  to  6500 

*Rates Subject to Change

 

Pelican Landing Antigua Room Vacation Condo Rental: 7082089

Pelican Landing Antigua Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Sunrise Suites Vacation Condo Rental: 7088388

Sunrise Suites

Description: Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 150  to  250 

*Rates Subject to Change

 

Coconut Cottage Vacation House Rental: 7091315

Coconut Cottage

Description: COCONUT COTTAGE -- Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the perfect escape for a couple or… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 2500  to  5100 

*Rates Subject to Change

 

Varela Cottage Vacation House Rental: 7091316

Varela Cottage

Description: VARELA COTTAGE - A true Conch cutie snuggled in Old Town. Varela Cottage is a one bedroom one bath cottage with loft including a 2nd… More

Bedrooms: 1
Sleeps: 4

*Rates: monthly, From: 1800  to  3500 

*Rates Subject to Change

 

Island Breeze Vacation House Rental: 7091317

Island Breeze

Description: ISLAND BREEZE -- Located in the exclusive Sanctuary within the Key West Golf Club, this spacious home allows for lots of visitors… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 3200  to  6600 

*Rates Subject to Change

 

Easy Livin' Vacation House Rental: 7091318

Easy Livin'

Description: EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 2000  to  9200 

*Rates Subject to Change

 

Sunset Lake Vacation Condo Rental: 7091320

Sunset Lake

Description: SUNSET LAKE -- Discover paradise and empty yourself of worries & hurries. Set at the end of a quiet lane, amid tropical landscaping,… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2600  to  5200 

*Rates Subject to Change

 

Ibis Vacation House Rental: 7091322

Ibis

Description: IBIS - Located in The Colony compound, Ibis is a wonderful one bedroom one bath condo, sparkling with new updates. Just a couple of… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 1800  to  3600 

*Rates Subject to Change

 

VO073 Vacation House Rental: 7097252

VO073

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 800  to  1100 

*Rates Subject to Change

 

VO503 Vacation House Rental: 7097254

VO503

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Porch/Patio: Yes More

Bedrooms: 1
Sleeps: 4

*Rates: weekly, From: 500  to  725 

*Rates Subject to Change

 

Pearl of Key West Vacation House Rental: 7107587

Pearl of Key West

Description: The Pearl of Key West is located on Elegant Emma St in prestigious Truman Annex, only a block away from World famous Duval Street… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 4000  to  6500 

*Rates Subject to Change

 

Key West Embrace Vacation Condo Rental: 7107588

Key West Embrace

Description: This 3 bedroom 3 bath condo has a beautiful view of the water and sunsets. You may sleep 7 people in this unit with a king bed both… More

Bedrooms: 3
Sleeps: 7

*Rates: weekly, From: 4000  to  5500 

*Rates Subject to Change

 

Treasure of the Tropics Vacation House Rental: 7107589

Treasure of the Tropics

Description: Sleeps: 8 Bedrooms: 4 Baths: 4 Bedding: 2 Queen, 2 King Description: \t\r When you are seeking one of the Best large home… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 5300  to  7300 

*Rates Subject to Change

 

Private Paradise Vacation House Rental: 7107590

Private Paradise

Description: Sleeps: 8 Bedding: 4 Queen Description: \t\r This Private home is located in the historic Truman Annex of old town Key West, where… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 5500  to  7500 

*Rates Subject to Change

 

Slice of Eden Vacation House Rental: 7107591

Slice of Eden

Description: Bedding: 3 Queen, 1 King Description: \t\r Luxurious water front home located in the heart of downtown Key West within walking… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 4500  to  6500 

*Rates Subject to Change

 

Key West Treasure Vacation House Rental: 7107592

Key West Treasure

Description: Bedding: 1 Queen, 1 King, 2 Twins, Trundle Description: \t\r If you are looking for an exclusive, tropical retreat, look no further!… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 3500  to  6500 

*Rates Subject to Change

 

Elegant Pineapple Vacation House Rental: 7107596

Elegant Pineapple

Description: Sleeps: 10 Bedrooms: 4 Baths: 3.5 Bedding: 2 Queen, 1 King, 2 Twins, Sleeper Sofa Description: \t\r If you are looking for an… More

Bedrooms: 4
Sleeps: 10

*Rates: weekly, From: 5000  to  9000 

*Rates Subject to Change

 

Tropical Temptations Vacation House Rental: 7107598

Tropical Temptations

Description: Sleeps: 8 Bedrooms: 4 Baths: 3.5 Bedding: 2 Queen, 1 King, 2 Twins Description: \t\r Fabulous sunset views, The owner's parents… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 3500  to  5500 

*Rates Subject to Change

 

The Haven Vacation House Rental: 7107599

The Haven

Description: leeps: 6 Bedrooms: Bedding: 2 Queen, 1 King Description: \t\r This 3 bedroom 4 bath home sits on Emma Street in Truman Annex. The… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 6000  to  9000 

*Rates Subject to Change

 

Admirals Private Retreat Vacation House Rental: 7107600

Admirals Private Retreat

Description: Bedding: 3 Queen Description: \t\r This home offers 3 bedrooms and 3 1/2 bathrooms. Located only 2 blocks away from Duval street and… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 4500  to  6500 

*Rates Subject to Change

 

Angel Palm Palace Vacation House Rental: 7107601

Angel Palm Palace

Description: Bedding: 1 Queen, 1 King, Sleeper Sofa, Trundle Description: \t\r This 3BR 3BA private home is in the exclusive Truman Annex on Emma… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 3500  to  5500 

*Rates Subject to Change

 

Tropical Serenity Vacation House Rental: 7107602

Tropical Serenity

Description: Bedding: 1 Queen, 1 King, 2 Twins convert to King, Sleeper Sofa Description: \t\r Tropical Serenity is located 2 blocks from Duval… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 2500  to  3500 

*Rates Subject to Change

 

Sunkissed Vision Vacation House Rental: 7107603

Sunkissed Vision

Description: Bedding: 2 King, Bunk Beds Description: \t\r View passing ships and sunsets from your own deck or balcony in the most prestigious… More

Bedrooms: 3
Sleeps: 7

*Rates: weekly, From: 3000  to  4500 

*Rates Subject to Change

 

Oceanview Spectacular Vacation House Rental: 7107606

Oceanview Spectacular

Description: Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise has 2000… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 3000  to  5000 

*Rates Subject to Change

 

Calypso Dreams Vacation House Rental: 7107607

Calypso Dreams

Description: Bedding: 2 Queen, 1 King, 2 Twins, 2 Twins convert to King, Sleeper Sofa Description: \t\r This stately home sits on beautiful Noah… More

Bedrooms: 5
Sleeps: 12

*Rates: weekly, From: 9000  to  9000 

*Rates Subject to Change

 

Southernmost Star Vacation House Rental: 7113715

Southernmost Star

Description: A classic 3 story Key West style town home that features 3 Bedrooms 3 1/2 Baths, custom made traditional pine wood floors, Beautiful… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 7000  to  10000 

*Rates Subject to Change

 

Octagon Island Vacation House Rental: 7113746

Octagon Island

Description: The residence was built in 1995. This unique home consists of two octagonal structures linked together and surrounded by airy… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 8800  to  8800 

*Rates Subject to Change

 

Olivia Cottage Vacation House Rental: 7113890

Olivia Cottage

Description: 30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 5000  to  7500 

*Rates Subject to Change

 

Newton Street Hideaway Vacation House Rental: 7113891

Newton Street Hideaway

Description: 30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 3200  to  5100 

*Rates Subject to Change

 

Tropical Serenity Vacation House Rental: 7113892

Tropical Serenity

Description: 30 DAY MINIMUM RENTAL An amazing renovation of mid town historic home with the Washington Street address many desire. This charming… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 4000  to  7000 

*Rates Subject to Change

 

Louisa's Private Courtyard Vacation House Rental: 7113893

Louisa's Private Courtyard

Description: Tucked behind a privacy gate, this garden setting L-shaped home is a perfect escape in the heart of Old Town. Louisa's Private… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 420  to  750 

*Rates Subject to Change

 

Suite Caroline - Mandarin Vacation Condo Rental: 7113895

Suite Caroline - Mandarin

Description: Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 2500  to  4000 

*Rates Subject to Change

 

Suite Caroline - Ginger Vacation Condo Rental: 7113896

Suite Caroline - Ginger

Description: Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 2500  to  4000 

*Rates Subject to Change

 

Suite Caroline - Sunset Vacation Condo Rental: 7113897

Suite Caroline - Sunset

Description: Turnday: Any. Amenities: More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 3000  to  5400 

*Rates Subject to Change

 

Suite Caroline - Splendor Vacation Condo Rental: 7113898

Suite Caroline - Splendor

Description: Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 2500  to  4000 

*Rates Subject to Change

 

Suite Caroline - Serenade Vacation Condo Rental: 7113899

Suite Caroline - Serenade

Description: Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully restored historic property sits… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 2800  to  4400 

*Rates Subject to Change

 

Townhomes on Windsor #1 Vacation House Rental: 7113900

Townhomes on Windsor #1

Description: Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 395  to  745 

*Rates Subject to Change

 

Townhomes on Windsor #2 Vacation House Rental: 7113901

Townhomes on Windsor #2

Description: Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 395  to  745 

*Rates Subject to Change

 

Townhomes on Windsor #3 Vacation House Rental: 7113902

Townhomes on Windsor #3

Description: Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 395  to  745 

*Rates Subject to Change

 

Townhomes on Windsor #4 Vacation House Rental: 7113903

Townhomes on Windsor #4

Description: Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 395  to  745 

*Rates Subject to Change

 

Townhomes on Windsor #5 Vacation House Rental: 7113904

Townhomes on Windsor #5

Description: Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 395  to  745 

*Rates Subject to Change

 

Little Torch Treasure Vacation House Rental: 7114498

Little Torch Treasure

Description: Unique Property that has its own private boat basin and boat ramp. Dockage, shopping, scuba diving, off shore fishing, back county… More

Bedrooms: 6
Sleeps: 12

*Rates: weekly, From: 5000  to  6500 

*Rates Subject to Change

 

Villa Key West Vacation House Rental: 7114710

Villa Key West

Description: Villa Key West is a spectacular oceanfront estate perfect for any occasion. Sit back and enjoy the Florida sunshine and the cool… More

Bedrooms: 6
Sleeps: 14

*Rates: monthly, From: 30000  to  30000 

*Rates Subject to Change

 

Southernmost Oasis Vacation House Rental: 7115765

Southernmost Oasis

Description: 3 bed/ 2 bath A Queen bed in each room Each bathroom complete with its own jacuzzi tub. Meticulously designed and decorated to be… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 6500  to  13000 

*Rates Subject to Change

 

Casa Aqua Vacation Villa Rental: 7116401

Casa Aqua

Description: Virtual Tour: Tour 1 Casa Aqua is a Spanish Mediterranean estate. The mansion, which can be rented separately or with the adjoining… More

Bedrooms: 6
Sleeps: 12

*Rates: nightly-weekday, From: 1372  to  1372 

*Rates Subject to Change

 

Casa Aqua Vacation Villa Rental: 7116402

Casa Aqua

Description: Virtual Tour: Tour 1 Casa Aqua is a Spanish Mediterranean estate. The mansion, which can be rented separately or with the adjoining… More

Bedrooms: 5
Sleeps: 10

*Rates: nightly-weekday, From: 1200  to  1200 

*Rates Subject to Change

 

Old Town Compound Vacation House Rental: 7116997

Old Town Compound

Description: 5 Bedrooms + Convertible bed(s), 4 Baths (Sleeps 10-14) The Captain's House was built in 1870 by the Chavez Family and is listed on… More

Bedrooms: 5
Sleeps: 14

*Rates: weekly, From: 4000  to  4000 

*Rates Subject to Change

 

VO373 Vacation House Rental: 7120267

VO373

Description: Turnday: Any. Amenities: Dockage: Yes Ocean/Bay Front: Yes Pool: Yes Dishwasher: Yes Porch/Patio: Yes Ice Maker: Yes More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1200  to  1450 

*Rates Subject to Change

 

VO382 Vacation House Rental: 7120269

VO382

Description: OCEANFRONT 2Bd/2Ba 35' concrete seawall with dock posts, cleats and swimming ladder, perfect those who love to boat. This resort… More

Bedrooms: 2
Sleeps: 4

*Rates: weekly, From: 1300  to  1600 

*Rates Subject to Change

 

VO411 Vacation House Rental: 7120276

VO411

Description: Beautifully renovated, sparkling clean and bright vacation home featuring 2Bd/2Ba with tile flooring throughout. Main living area… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 680  to  1100 

*Rates Subject to Change

 

Manatee Bay Vacation House Rental: 7123132

Manatee Bay

Description: SPECIAL LOBSTER RATE JULY 23- JULY 30, 2011.Great gulf side boating is at your fingertips and just a short run out to the Atlantic… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2500  to  2800 

*Rates Subject to Change

 

Blue Heron Vacation House Rental: 7123471

Blue Heron

Description: This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2350  to  2500 

*Rates Subject to Change

 

Blue Marlin Vacation House Rental: 7123472

Blue Marlin

Description: Spacious and comfortable for 6 people in this 3 bedroom, 2 bath, Little Torch Key home. Located down a private lane and overlooking… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3500  to  3800 

*Rates Subject to Change

 

Quiet Waters Vacation House Rental: 7123474

Quiet Waters

Description: Brand new in 2007 with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2400  to  2600 

*Rates Subject to Change

 

Coral House Vacation House Rental: 7123476

Coral House

Description: Conveniently located on Ramrod Key, mile marker 28. Close to all the choice restaurants and services that the Florida Keys have to… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3000  to  3500 

*Rates Subject to Change

 

Group Therapy Vacation House Rental: 7123477

Group Therapy

Description: The spacious 2 bedroom 2 bath home is expertly decorated in cool tropical colors. The open water views over Sugarloaf Sound are just… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3900  to  4000 

*Rates Subject to Change

 

Galleon Bay Vacation House Rental: 7123614

Galleon Bay

Description: This home is centrally located 23 miles from Key West and 25 Miles to Marathon. There is so much to do and see just a quick trip… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2500  to  2900 

*Rates Subject to Change

 

Keys Escape Vacation House Rental: 7124411

Keys Escape

Description: Just the spot to unwind and let your hair down. 3 bedrooms and 3 baths plus recreation room for the kids to get away. Open and airy… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 4500  to  5000 

*Rates Subject to Change

 

Duval Breeze Vacation House Rental: 72837

Duval Breeze

Description: DUVAL BREEZE - Enjoy the great location offered by this beautiful 2 bedroom 2.5 bath townhome located in the gated rooftop community… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 30  to  435 

*Rates Subject to Change

 

Key West Found Vacation House Rental: 72839

Key West Found

Description: KEY WEST FOUND – A striking two bedroom, two and half bath townhome located in the historic brick Foundry building within the Truman… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 600  to  3190 

*Rates Subject to Change

 

Villa Soleil Vacation House Rental: 72842

Villa Soleil

Description: VILLA SOLEIL -- Located in the historic Foundry building of Truman Annex, a beautiful gated community in the heart of Old Key West,… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 600  to  3190 

*Rates Subject to Change

 

Bahama Dreaming Vacation House Rental: 72846

Bahama Dreaming

Description: BAHAMA DREAMING is a beautifully renovated Conch house conveniently located in the center of Old Town, one block behind celebrated… More

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekday, From: 130  to  804.75 

*Rates Subject to Change

 

Amelia Home Vacation House Rental: 72848

Amelia Home

Description: AMELIA HOME - A private Key West vacation home that is only four blocks from the Atlantic Ocean and one of Key West's most popular… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 130  to  681.5 

*Rates Subject to Change

 

Tropical Dreaming Vacation House Rental: 72849

Tropical Dreaming

Description: TROPICAL DREAMING -- This tropical 2-bedroom home has been professionally decorated and furnished. There are classic art features,… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 130  to  681.5 

*Rates Subject to Change

 

The Victoria House Vacation House Rental: 72851

The Victoria House

Description: THE VICTORIA HOUSE (Formerly Treetop Villa) - This gracious historical property, dating from the early 20th century, was built by… More

Bedrooms: 5
Sleeps: 12

*Rates: nightly-weekday, From: 375  to  1670 

*Rates Subject to Change

 

Secret Villa Vacation House Rental: 76139

Secret Villa

Description: A hideaway on Freeschool Lane This unique villa is hidden away on the end of the quiet lane just a step away from Duval Street.… More

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekday, From: 450  to  790 

*Rates Subject to Change

 

Colony Cabana Vacation Condo Rental: 76140

Colony Cabana

Description: Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 160  to  313 

*Rates Subject to Change

 

Colony Poolside Vacation Bungalow Rental: 76142

Colony Poolside

Description: Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom… More

Bedrooms: 1
Sleeps: 2

*Rates: nightly-weekday, From: 160  to  313 

*Rates Subject to Change

 

Beach Club #204 Vacation Condo Rental: 76147

Beach Club #204

Description: Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This is one of the most… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 330  to  480 

*Rates Subject to Change

 

Duval Square Retreat Vacation Condo Rental: 76149

Duval Square Retreat

Description: Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and more quiet end of Duval Street.… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 250  to  410 

*Rates Subject to Change

 

Atlantis Vacation House Rental: 77991

Atlantis

Description: Everyday is a great day at Atlantis. Beautiful Big Pine home located just minutes to Bogie Channel. This channel affords direct… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3000  to  3000 

*Rates Subject to Change

 

Linger Longer Vacation House Rental: 82030

Linger Longer

Description: LINGER LONGER -- Enjoy an easy vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome located in the President's Walk… More

Bedrooms: 2
Sleeps: 5

*Rates: weekly, From: 500  to  2610 

*Rates Subject to Change

 

31018 Atlantis Dr Vacation House Rental: 85606

31018 Atlantis Dr

Description: Turnday: Any. Amenities: Dockage: Yes Dishwasher: Yes Porch/Patio: Yes More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3000  to  3000 

*Rates Subject to Change

 

Anne's Hideaway Vacation House Rental: 88157

Anne's Hideaway

Description: ANNE'S HIDEAWAY - Relax and unwind in this historic Conch home with original Key West architecture. Tucked away in a quiet area of… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2200  to  6500 

*Rates Subject to Change

 

Key Lime Pie Vacation House Rental: 88161

Key Lime Pie

Description: KEY LIME PIE - A little slice of paradise located only one block from the historic seaport and close enough to bike to all the sites… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2500  to  5100 

*Rates Subject to Change

 

Artist House Vacation House Rental: 88163

Artist House

Description: ARTIST HOUSE - Welcome to the Artist House located within the gated rooftop community of Duval Square. Beautifully decorated with… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekday, From: 75  to  456.75 

*Rates Subject to Change

 

Sunny Days Vacation House Rental: 88164

Sunny Days

Description: SUNNY DAYS - Beautifully maintained while retaining its original style and structure. Dade County pine is throughout the property… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 1800  to  4300 

*Rates Subject to Change

 

Conch Escape Vacation House Rental: 88166

Conch Escape

Description: CONCH ESCAPE - Monthly Rental Only. Two bedroom, two bath cottage in a quiet Old Town neighborhood. This property has brand new… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2200  to  5400 

*Rates Subject to Change

 

Artist Garden Vacation House Rental: 88167

Artist Garden

Description: ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of the… More

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 600  to  3625 

*Rates Subject to Change

 

Atlantic Blues Vacation House Rental: 88168

Atlantic Blues

Description: ATLANTIC BLUES - Is a stylish example of a Conch cottage, totally renovated with gorgeous hardwood floors, beautiful glass tiles,… More

Bedrooms: 1
Sleeps: 4

*Rates: monthly, From: 2500  to  5100 

*Rates Subject to Change

 

A Suite Paradise Vacation House Rental: 88169

A Suite Paradise

Description: A SUITE PARADISE - This lovely home is truly a tropical hideaway tucked away in a secluded Key West neighborhood yet minutes from… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 3000  to  7300 

*Rates Subject to Change

 

Josephine Vacation House Rental: 88171

Josephine

Description: JOSEPHINE -Tastefully furnished two bedroom two bath private single family home with bedding for four. This property features a… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2000  to  5000 

*Rates Subject to Change

 

Corner Place Vacation House Rental: 88175

Corner Place

Description: CORNER PLACE - Come to Key West where the sun always shines!! Stay in a beautiful two bedroom one bath in the gated Key West Golf… More

Bedrooms: 2
Sleeps: 4

*Rates: monthly, From: 2500  to  3600 

*Rates Subject to Change

 

Casa Flora Vacation House Rental: 88177

Casa Flora

Description: CASA FLORA - This lovely home overlooks the greens at the Key West Golf Club. On the first floor of the home you will find the… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 2600  to  6000 

*Rates Subject to Change

 

Catherine House Vacation House Rental: 89119

Catherine House

Description: This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, or shopping on Duval… More

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekday, From: 270  to  400 

*Rates Subject to Change

 

Canal Front Home, Dock, 3 Bedrm 2 Bath, Relaxing in the Keys Vacation House Rental: 901503

Canal Front Home, Dock, 3 Bedrm 2 Bath, Relaxing in the Keys

Description: The interior of the house has the keys influence in decor and an open floor plan. Great for visiting while in the kitchen, dining… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 3000  to  3000 

*Rates Subject to Change

 

Location, Location, Location! Ocean View, Lagoon Beach Front Vacation House_boat Rental: 903627

Location, Location, Location! Ocean View, Lagoon Beach Front

Description: This 83' Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 2. The property is furnished and includes: linens,… More

Bedrooms: 3
Sleeps: 10

*Rates: extra-night, From: 350  to  350 

*Rates Subject to Change

 

'CONCH CASITA 2 @ ELIZABETH': Charmingly Renovated 1.5BR/1BA Old Town Cottage... Vacation Condo Rental: 904143

'CONCH CASITA 2 @ ELIZABETH': Charmingly Renovated 1.5BR/1BA Old Town Cottage...

Description: This wonderful little cottage is the sister to 'Conch Casita 3' and is right next door. Located on 720 Elizabeth Street, a quiet… More

Bedrooms: 2
Sleeps: 3

*Rates: monthly, From: 2950  to  5500 

*Rates Subject to Change

 

'CASITA CORALINA @ GRINNELL': Charming 2BR/3BA Conch Cottage in Old Town... Vacation House Rental: 904144

'CASITA CORALINA @ GRINNELL': Charming 2BR/3BA Conch Cottage in Old Town...

Description: This precious 2 bedroom cottage with its coral shutters will charm you from the moment you walk in the front gate. The front porch… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 6600  to  9900 

*Rates Subject to Change

 

“GULFSIDE VISTAS @ TRUMAN ANNEX': Luxury Oceanfront 2BR/2.5BA Penthouse Condo... Vacation Condo Rental: 904145

“GULFSIDE VISTAS @ TRUMAN ANNEX': Luxury Oceanfront 2BR/2.5BA Penthouse Condo...

Description: This beautiful penthouse condo is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise… More

Bedrooms: 2
Sleeps: 5

*Rates: monthly, From: 9000  to  17000 

*Rates Subject to Change

 

Dock Your Boat at Your Front Door I Vacation House Rental: 905551

Dock Your Boat at Your Front Door I

Description: As the day dawns over Pine Channel and the spectacular sunrise greets you each morning it will be hard to decide where to have your… More

Bedrooms: 3
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Rock Your World on Open Water! *Special Offers for August & September* Vacation House Rental: 906464

Rock Your World on Open Water! *Special Offers for August & September*

Description: * Serenity now! * Refuge from the ordinary! * Escape the chaos of the overcrowded beach scene! * Unforgettable memories at an… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 2800  to  3500 

*Rates Subject to Change

 

Key West luxury beachside w/ all modern ammenities Vacation Condo Rental: 907224

Key West luxury beachside w/ all modern ammenities

Description: This is one of the best units at 1800 Atlantic Condominiums. You feel as though you are deep in the Caribbean with the tropical… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4499  to  6499 

*Rates Subject to Change

 

Blue Lagoon Vacation Townhome Rental: 908572

Blue Lagoon

Description: Welcome to ''Blue Lagoon'' located in prestigious Truman Annex, in the President's Walk and Southard Street area. This luxurious 3… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2500  to  3500 

*Rates Subject to Change

 

Waterfront Views from Dolphin Watch Vacation House Rental: 908577

Waterfront Views from Dolphin Watch

Description: Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than two blocks… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 4500  to  6500 

*Rates Subject to Change

 

Historic Tropical Beauty Vacation House Rental: 909093

Historic Tropical Beauty

Description: Beautiful open bedroom with wood floors overlooking downstairs & view of the garden. Large bathroom & shower with dual shower heads,… More

Bedrooms: 1
Sleeps: 4

*Rates: monthly, From: 1800  to  4500 

*Rates Subject to Change

 

One of a Kind Luxury Home - Admirals Treasure Vacation House Rental: 910431

One of a Kind Luxury Home - Admirals Treasure

Description: This is a one of a kind luxury home located in prestigious Truman Annex. We offer 4500 square feet that features 4 BR and 4BA, a 30… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 5500  to  7500 

*Rates Subject to Change

 

Upscale and Spacious Waterfront Property Vacation House Rental: 911039

Upscale and Spacious Waterfront Property

Description: Beautiful and spacious property located in Prestigious Sugarloaf Shores Estates. The house offers breathtaking sunset views over the… More

Bedrooms: 2
Sleeps: 8

*Rates: monthly, From: 7100  to  7100 

*Rates Subject to Change

 

One year old home on clean canal with 60 feet of docking space Vacation House Rental: 911492

One year old home on clean canal with 60 feet of docking space

Description: If you like fishing, diving or just relaxing this is the place! Deep water clean canal short ride out to the ocean or back counrty.… More

Bedrooms: 3
Sleeps: 7

*Rates: monthly, From: 2850  to  3200 

*Rates Subject to Change

 

This 2003 Hunter Sailboat Vacation Yacht Rental: 914435

This 2003 Hunter Sailboat

Description: Stay aboard a beautiful sailing yacht with all the amenities of home. I can arrange packages for you to include sailing, diving,… More

Bedrooms: 2
Sleeps: 7

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Old Town Key West Paradise! Vacation House Rental: 914711

Old Town Key West Paradise!

Description: Unwind, kick back, and enjoy the beauty and tranquility of island living in a private home, amidst tropical gardens, close to… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Oceanfront Condominium - Direct Oceanfront at the Coral Reef Vacation Condo Rental: 154612

Oceanfront Condominium - Direct Oceanfront at the Coral Reef

Description: You feel it the moment you arrive. The warm tropical breezes, the blue green water. It's a rhythm. A rhythm set into motion over a… More

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 250  to  390 

*Rates Subject to Change

 

Relaxing, quiet, get-away just blocks from downtown Key West & Beach - MONTHLY Vacation House Rental: 223317

Relaxing, quiet, get-away just blocks from downtown Key West & Beach - MONTHLY

Description: This newly renovated home is perfect for a family or group of friends who want to get away and become 'temporary residents' of the… More

Bedrooms: 3
Sleeps: 8

*Rates: monthly, From: 2700  to  6500 

*Rates Subject to Change

 

Bo's Tropical Get-a-Way at Venture Out in the Florida Keys Vacation House Rental: 234389

Bo's Tropical Get-a-Way at Venture Out in the Florida Keys

Description: Free use of two Ocean Kayaks during your stay. Dock your boat behind the 2 bedroom/2 bathroom nicely decorated rental unit on a deep… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Rose Lane Villa's Villa Porta 1 bedroom, 1/2 block off Duval Vacation Villa Rental: 299236

Rose Lane Villa's Villa Porta 1 bedroom, 1/2 block off Duval

Description: Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekend, From: 149  to  169 

*Rates Subject to Change

 

“THE AVIARY NEST @ ARONOVITZ LANE': 2BR/2BA Cottage in Old Town, Pool... Vacation House Rental: 390178

“THE AVIARY NEST @ ARONOVITZ LANE': 2BR/2BA Cottage in Old Town, Pool...

Description: This charming conch cottage is located on 404 Aronovitz Lane, a little cul-de-sac just off Angela Street half a block from Duval.… More

Bedrooms: 2
Sleeps: 6

*Rates: monthly, From: 4400  to  8500 

*Rates Subject to Change

 

2 Bedroom Garden-View Condo at 1800 Atlantic Vacation Condo Rental: 390413

2 Bedroom Garden-View Condo at 1800 Atlantic

Description: Perfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully… More

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

PET FRIENDLY COTTAGE Vacation Cottage Rental: 391123

PET FRIENDLY COTTAGE

Description: Charming cottage comes complete with a kitchenette packed with all the necessities for a great Key West vacation. Nothing's been… More

Bedrooms: 0
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Tropical Retreat Vacation Cottage Rental: 391129

Tropical Retreat

Description: Lush gardens surround this lovingly restored two-story Bahamian house. This upstairs suite has two bedrooms each featuring a queen… More

Bedrooms: 2
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Tropical Village Cottage Vacation Cottage Rental: 391130

Tropical Village Cottage

Description: Tropical Village Cottage - is the epitome of modern Key West. This two bedroom, two bath conch cottage overlooks a shared… More

Bedrooms: 2
Sleeps: 5

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

Tropical Hideaway Vacation Cottage Rental: 391133

Tropical Hideaway

Description: Lush gardens surround this lovingly restored two-story Bahamian house. This downstairs suite has one bedrooms with full bath and… More

Bedrooms: 1
Sleeps: 4

*Rates: …, From: …  to  … 

*Rates Subject to Change

 

VO182 Vacation House Rental: 7034345

VO182

Description: Turnday: Any. Amenities: Dockage: Yes Pool: Yes Porch/Patio: Yes More

Bedrooms: 1
Sleeps: 6

*Rates: weekly, From: 750  to  899 

*Rates Subject to Change

 

Shipyard 210 - 4 Vacation House Rental: 7042520

Shipyard 210 - 4

Description: The first floor includes a front porch, bedroom, completely remodeled kitchen, remodeled lower bathroom, large open living area, and… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 2200  to  3500 

*Rates Subject to Change

 

Pelican landing Eleuthera Room Vacation Condo Rental: 7067985

Pelican landing Eleuthera Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pelican Landing Curacao Room Vacation Condo Rental: 7081777

Pelican Landing Curacao Room

Description: Come stay at our beautiful waterfront condos. Whether you want a suite for two or a retreat for up to fourteen guests you will enjoy… More

Bedrooms: 1
Sleeps: 4

*Rates: nightly-weekday, From: 100  to  200 

*Rates Subject to Change

 

Pearl of Key West Vacation House Rental: 7107587

Pearl of Key West

Description: The Pearl of Key West is located on Elegant Emma St in prestigious Truman Annex, only a block away from World famous Duval Street… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 4000  to  6500 

*Rates Subject to Change

 

Key West Embrace Vacation Condo Rental: 7107588

Key West Embrace

Description: This 3 bedroom 3 bath condo has a beautiful view of the water and sunsets. You may sleep 7 people in this unit with a king bed both… More

Bedrooms: 3
Sleeps: 7

*Rates: weekly, From: 4000  to  5500 

*Rates Subject to Change

 

Slice of Eden Vacation House Rental: 7107591

Slice of Eden

Description: Bedding: 3 Queen, 1 King Description: \t\r Luxurious water front home located in the heart of downtown Key West within walking… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 4500  to  6500 

*Rates Subject to Change

 

Elegant Pineapple Vacation House Rental: 7107596

Elegant Pineapple

Description: Sleeps: 10 Bedrooms: 4 Baths: 3.5 Bedding: 2 Queen, 1 King, 2 Twins, Sleeper Sofa Description: \t\r If you are looking for an… More

Bedrooms: 4
Sleeps: 10

*Rates: weekly, From: 5000  to  9000 

*Rates Subject to Change

 

Tropical Temptations Vacation House Rental: 7107598

Tropical Temptations

Description: Sleeps: 8 Bedrooms: 4 Baths: 3.5 Bedding: 2 Queen, 1 King, 2 Twins Description: \t\r Fabulous sunset views, The owner's parents… More

Bedrooms: 4
Sleeps: 8

*Rates: weekly, From: 3500  to  5500 

*Rates Subject to Change

 

Admirals Private Retreat Vacation House Rental: 7107600

Admirals Private Retreat

Description: Bedding: 3 Queen Description: \t\r This home offers 3 bedrooms and 3 1/2 bathrooms. Located only 2 blocks away from Duval street and… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 4500  to  6500 

*Rates Subject to Change

 

Angel Palm Palace Vacation House Rental: 7107601

Angel Palm Palace

Description: Bedding: 1 Queen, 1 King, Sleeper Sofa, Trundle Description: \t\r This 3BR 3BA private home is in the exclusive Truman Annex on Emma… More

Bedrooms: 3
Sleeps: 8

*Rates: weekly, From: 3500  to  5500 

*Rates Subject to Change

 

Oceanview Spectacular Vacation House Rental: 7107606

Oceanview Spectacular

Description: Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise has 2000… More

Bedrooms: 3
Sleeps: 6

*Rates: weekly, From: 3000  to  5000 

*Rates Subject to Change

 

Calypso Dreams Vacation House Rental: 7107607

Calypso Dreams

Description: Bedding: 2 Queen, 1 King, 2 Twins, 2 Twins convert to King, Sleeper Sofa Description: \t\r This stately home sits on beautiful Noah… More

Bedrooms: 5
Sleeps: 12

*Rates: weekly, From: 9000  to  9000 

*Rates Subject to Change

 

Southernmost Star Vacation House Rental: 7113715

Southernmost Star

Description: A classic 3 story Key West style town home that features 3 Bedrooms 3 1/2 Baths, custom made traditional pine wood floors, Beautiful… More

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 7000  to  10000 

*Rates Subject to Change

 

Newton Street Hideaway Vacation House Rental: 7113891

Newton Street Hideaway

Description: 30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and… More

Bedrooms: 1
Sleeps: 2

*Rates: monthly, From: 3200  to  5100 

*Rates Subject to Change

 

Villa Key West Vacation House Rental: 7114710

Villa Key West

Description: Villa Key West is a spectacular oceanfront estate perfect for any occasion. Sit back and enjoy the Florida sunshine and the cool… More

Bedrooms: 6
Sleeps: 14

*Rates: monthly, From: 30000  to  30000 

*Rates Subject to Change

 
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