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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Call For Availability and Pricing
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
1½ Baths
Sleeps 5
Type of property: Townhouse
Area: Old Town

LINGER LONGER: Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome in the President's Walk of Truman Annex, a gated community located within Old Town Key West. This property is conveniently situated poolside and just a short walk to the many restaurants, attractions and shopping that make Key West so special.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

ATLANTIC PARADISE -- Imagine the ocean only several yards from your balcony, in a secure gated complex, with all the amenities you could ask for -- Olympic-sized pool, Jacuzzi, tennis courts, covered garage parking.  Make the most of visiting our island Paradise by staying on the ocean within a quick bike ride from the action of Duval Street.


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2 Bedrooms
2 Baths
Sleeps 6
Type of property: Condo
Area: Ocean Side

BRISA DEL MAR: This 2 bedroom, 2 bath condominium is located oceanfront in a gated community with a spectacular view of the Atlantic Ocean. Walk across the street to the beach and rent umbrellas, chairs, kayaks; enjoy a sno-cone after playing volleyball or just sit on your balcony and relax in the tropical breezes with a margarita.  Now, this is livin'...


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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
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

KEY WEST CHARMING: This downstairs 2 bedroom 1 bath Shipyard condo is located in prestigious Truman Annex, a gated community within Old Town Key West. Take advantage of the ideal location and convenience of walking to anything you would want to do while visiting our lovely island. Prepare to be charmed.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse
Area: Stock Island

KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo.  Located in the exclusive Key West Golf Club Community you will enjoy a beautifully manicured landscaped grounds, a fabulous pool with waterfall and access to the fitness facility.


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

LEEWARD ISLE KEY WEST RETREAT: Dwell in the possibility! 2 bedrooms 2 baths in this newly renovated residence. From the moment you park in the private parking lot, you know you are someplace special. A small gated compound with only 13 homes, you will revel in the peace and quiet, while still being located right in the heart of Old Town.


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2 Bedrooms
3 Baths
Sleeps 6
Type of property: Townhouse
Area: Stock Island

CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you. This 2 bedroom 2.5 bath townhome in the gated community of Coral Hammock has all the comforts including flatscreen TVs, washer/dryer, private parking, and convenient to some of our local favorite restaurants, beach and airport.


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

NAUTICAL DREAMS (monthly rental): Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2 bedroom 2 bath home, in a small compound of 8 cottages, opens from each bedroom and the living room onto a grand private deck with ample space for entertaining or relaxing with a book. Walking through this well-established local neighborhood is an added bonus.


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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.


Call For Availability and Pricing
2 Bedrooms
2 Baths
Sleeps 5
Type of property: Condo
Area: Old Town

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in secluded Truman Annex. Lots of open spaces, perfect for entertaining or keeping it low-key and intimate. Easy walking distance to all Key West has to offer.


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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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4 Bedrooms
3½ Baths
Sleeps 8
Type of property: Private 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
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

SUNSET CELEBRATION: 2 bedroom 1 bath Shipyard condo located in Truman Annex, in walking distance of anything you want to explore on our island paradise.  Newly renovated with a bright, tropical flair and fully stocked with all the conveniences of home.    Clean, serene and ready to make your visit to Key West one you'll cherish for years to come.


 

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