Key West Vacation Rentals

Gated Community ~ Key West Vacation Condo Rentals in Florida

Most condo rentals in Key West, FL are located in a premier gated community. The assurance of such privacy is a comfort for all travelers whether you're with a group of friends or traveling with young ones. Our gated community vacation rentals are very popular among guests for their exclusive access to amenities like community pools, hot tub and children's park and yet close to most if not all Key West activities. These extras can go a long way in keeping everyone entertained during any down time you may have during your Key West getaway.
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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

4 PALMS: 2 bedroom 2 bath condominium with sleeper sofa offers your family the peace and tranquility you want while home, within minutes of the hectic lifestyle of downtown. Condo complex offer jacuzzi, pool, BBQ and tennis courts for your vacation pleasure. Located next to Smathers Beach where you can walk to promenade on the Atlantic Ocean witnessing magnificent sunrise.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

Breezy Bungalow - Weekly Rental When a name says it all you know you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and Fench doors open to allow sunshine and seaside breezes to flow openly.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Condo
Area: Old Town

CONCH CONDO: This 2 bedroom 2 bath second-floor condo features a fully-equipped kitchen, home theatre in the living room, plasma TVs in both bedrooms, soaring cathedral ceilings with ceiling fans and central air conditioning. Located in Truman Annex within walking distance of everything Key West has to offer; you have found a true Paradise.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

KEY WEST FOUND:   A striking 2 bedroom, 2.5 bath townhome located in the historic  Foundry building in Truman Annex. This 3-story townhome has all the comforts of home.  Conveniently located within walking distance of all the best of Key West -- tourist attractions, beach, Duval Street, Sunset celebration -- you will never want to leave.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse

THE GALLERY - This is a very unique home where the original owner has kept this little treasure all to herself and now wants to share it with you!  An accomplished artist, the home is filled with her original artwork of favorite things in Key West.  Excellent location in Key West Golf Club with the community pool just outside the back steps with easy access to the clubhouse and library.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL BREEZE:  Enjoy the great location of  this beautiful 2 bedroom 2.5 bath townhome located in the gated rooftop community of Duval Square. This great location is steps away from fantastic restaurants, nightlife, bars and shopping on Duval Street in Old Town Key West.  Check out chaotic Duval Street, then relax  on your private balcony.  Ahhh...


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL SEA TURTLE: This 2 bedroom 2.5 bath townhome with sleeper sofa offers comfort and space for a family of six. Conveniently located in the rooftop townhome community of Duval Square, you are close enough to the eclectic activity of Duval Street, and far enough to enjoy peace and quiet in the privacy of your own home.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Cottage
Area: Old Town

SUNNY DAYS - Monthly rental Key West, beautifully maintained while retaining its original style and structure. Dade County pine is throughout the property, lots of French doors and windows to bring in the sunshine, and lots of privacy within the cottage grounds and within the compound community. 


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4 Bedrooms
3½ Baths
Sleeps 8
Type of property: Home
Area: Old Town

THE DOLPHIN HOUSE: The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between. Plenty of room for friends or family gatherings.  Located in Truman Annex within walking distance of all Key West has to offer.  


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

SPA ON DUVAL: A tropical 2-story, 2 bedroom 2.5bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, specialty shops and the action of Duval Street. Catch the rays on the pool deck or soothe tired muscles in the private jacuzzi on your own deck. Spa On Duval is truly a Key West experience to enjoy.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Condo
Area: Old Town

BEACH HOUSE CONDO:   A beautiful 2 bedroom 2 bath Shipyard condominium, located in the prestigious Truman Annex community. This gated community in Old Town Key West is ideal -- only 2 blocks from bars, restaurants and shopping on famous Duval Street and walking distance to all of the attractions you came here to see.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL ON THE SQUARE (monthly rental):  Located at the Duval Square townhomes directly on Duval but above all the hubbub. The townhomes are built on the second and third story of the complex with community pool overlooking Duval Street. This lovely 2 bedroom 2.5 bath townhome is available for a relaxing, luxurious month in Paradise.


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1 Bedroom
1 Bath
Sleeps 2
Type of property: Condo
Area: Old Town

CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This is the place! Centrally located in Truman Annex, smart, sleek and modern with fully equipped kitchen and high-end electronics within two blocks of anything you'll want to do in our island Paradise.


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3 Bedrooms
4 Baths
Sleeps 8
Type of property: Home
Area: Old Town

EASY LIVIN': The name says it all! This lovely private 3 bedroom home with pool is located in a secluded cul-de-sac in Truman Annex, a gated community located in historic Old Town Key West. Lounge by the pool in peace and tranquility or take a short walk to Duval Street where you will find the restaurants, bars, and shopping you have heard so much about.


 

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