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Community Pool ~ Vacation Rentals ~ Key West ~ Amenities

Rental condos in Key West offer guests exclusive access to the community pool where families and children can spend a day lounging poolside or playing water games. Heated community pools are a popular amenity and a great addition to any vacation rental in Key West when you find the beach is bustling with too many travelers or you have small children that you'd like to keep an eye on. Work on your tan while you enjoy the latest best-seller at your rental's community pool. Comfortable beach chairs and tables with umbrellas where you can enjoy a picnic are on hand to help complete your day.

Your search has found 59 homes
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Showing homes 1 - 25 of 59

OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
1 bath
 

IBIS (monthly rental): Ibis is a wonderful 1 bedroom 1 bath home that shares the pool and laundry facilities in The Colony Suites compound. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. Live like a local and find out why we call Key West our island paradise.



OLD TOWN 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1 bath
 

EMMA'S ESCAPE (monthly rental): Beautiful and spacious 2 bedroom 1 bath ground-level condo located in historic Old Town's Bahama Village neighborhood. Emma’s Escape is one of four condos that share the large landscaped backyard, complete with jacuzzi, pool and tiki hut. Live like a local and you will know why we call it Paradise.



GOLF COURSE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
2.5 baths
 

BIRD'S NEST (monthly rental): Come to Key West, where the sun always shines! Stay in a beautiful 2 bedroom 2.5 bath townhome in the gated Key West Golf Club community. Stroll in quiet solitude through the manicured grounds, relax by the pool, play a round of golf. You're close to it all - beaches, downtown, the airport and some of Key West locals' favorite bars/restaurants.



OLD TOWN 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1 bath
 

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
1.5 baths
$1,300 -
$2,610

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.



OCEAN SIDE 2 Bed Home - Monthly Key West, FL 2 bedrooms
2.5 baths
 

A DOCKSIDE VILLA - Beautiful, 2 bedroom 2.5 bath townhome with spectacular views of Florida Bay and your own dock just steps from your door. Enjoy one of Key West’s rare waterfront communities located in walking distance to Garrison Bight. Enjoy all that Key West has to offer in this picture perfect setting.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$220 -
$2,188

FLORIDA PALM: 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.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$1,600 -
$3,190

ISLAND SPICE: Lovely 2 bedroom, 2.5 bath townhome, located in the historic Foundry building of Truman Annex. Exposed brick inside and out gives you an Old Town cozy feel, yet this newly updated home has a trendy tropical flair. Enjoy your secluded front patio for cocktails and BBQ. And when you are ready to party in a crowd, Duval Street is a mere 2 blocks away.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

CONCH ESCAPE (monthly rental): 2 bedroom 2 bath cottage in a quiet Old Town neighborhood, this property has a renovated kitchen and other recent updates making it comfortable and inviting. Enjoy a cocktail on the private deck in your own backyard, or stroll over the the pool shared by an intimate group of neighbors.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$220 -
$2,188

PAPAYA PLACE: This spacious 2 bedroom 2 bath condominium at 1800 Atlantic offers a wonderful relaxing view of the nature preserve next door and the ocean beyond. Well-equipped with all the modern conveniences. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing you to be lost in the tropical breezes.



GOLF COURSE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1.5 baths
 

LAKEVIEW (monthly rental): Come to Key West where the sun always shines!! Stay in a beautiful 2 bedroom 1.5 bath bungalow in the gated Key West Golf Club community. Stroll the lushly landscaped grounds, relax in the pool, play a round of golf, and when you venture out, you will be close to it all - beaches, downtown and some of our favorite local restaurants.



GOLF COURSE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1 bath
 

CORNER PLACE (monthly rental): Come to Key West where the sun always shines! Stay in a beautiful 2 bedroom 1 bath home in the gated Key West Golf Club community where you can stroll through lushly landscaped grounds, relax at the pool, tone up in the fitness center, or sip a cocktail on your screened porch, thankful to be in Paradise.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$345 -
$3,369

KEY WEST CROWN JEWEL: We know that you will enjoy staying in our little bit of Paradise. This is a 2 bedroom, 2 bath Penthouse condominium with 1350 square feet of living space. Located on the Atlantic Ocean with magnificent views from every room. A short bike ride downtown and you are in the midst of what has made Duval Street infamous: bars, restaurants, and galleries galore.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
1 bath
 

LAND'S END - A rare find tucked away in the Seaport district of Land’s End is an Old Town treasure awaiting your arrival! Nestled in a compound half a block off Caroline Street (yes, the same street of Jimmy Buffett fame!), you will find your own piece of Paradise. Perfect for one or two adventurous souls who enjoy being close to the action.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
1 bath
$1,100 -
$2,320

LAVENDER JUNGLE: Beautiful 2 bedroom 1 bath downstairs Shipyard condo in Truman Annex with back deck that opens to the entrance of Fort Zachary Taylor State Park, one of the nicest beaches on the island. Truman Annex, a secure gated community within Old Town Key West, is within walking distance of all the favorite hotspots on the island.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$225 -
$2,610

CARIBBEAN DUVAL:  Nestled above Duval Street in the heart of the Art district, this lovely 2 bedroom, 2.5 bath townhouse, a spacious 1,300 sq. ft. hideaway, features central A/C and an open floor plan with a half bath on the first floor and a full bath in each bedroom upstairs. Duval Square, a gated, secure rooftop community with pool is centrally located in Old Town Key West.



OLD TOWN 2 Bed Condo - Monthly Key West, FL 2 bedrooms
2 baths
 

SOUTHARD RETREAT (monthly rental): This is a choice location with lush tropical garden and beautiful swimming pool offering a peaceful setting behind the privacy wall, yet just a few blocks from the eclectic activity of Old Town Key West. 2 bedrooms 2 baths located in the Southard Square condominium complex with off-street parking.



GOLF COURSE 3 Bed Home - Monthly Key West, FL 3 bedrooms
3 baths
 

SUNSET LAKE (monthly rental): Discover Paradise and leave your worries back home. This 3 bedroom 3 bath townhome exudes an ambiance of peace and tranquility. Located in the exclusive gated community, Key West Golf Club, you can stroll the grounds, sun at the pool, play a round of golf, or sit on your porch watching the local wildlife congregate at the lake.



OLD TOWN 1 Bedroom Home Key West, FL 1 bedroom
1 bath
$190 -
$2,248

EGRET COTTAGE: Enjoy your own sweet 1 bedroom cottage with private deck in a charming compound nestled in the heart of historic Old Town Key West, two blocks from Duval Street with its incredible art galleries, boutiques, museums, attractions, restaurants, and nightclubs. Close enough when you want it, far enough when you don't.



OCEAN SIDE 3 Bedroom Condo Key West, FL 3 bedrooms
2 baths
$375 -
$4,188

SURF SIDE - Search no further! This fabulous condominium is directly on the Atlantic Ocean. Located at the end of the building closest to the beach, the balcony wraps around offering full ocean views from the 3 bedrooms and the living room. Stylish furnishings, well-equipped kitchen and all the modern conveniences are here for your pleasure.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$250 -
$2,755

ISLAND WIND: Welcome to a tropical sun-drenched oasis in the heart of Old Town. This charming 2 bedroom 2 bath Bahamian-style townhome, with tin roof and white spindled decks reminiscent of Old Key West, is located in award-winning Windward Park, a gated and secure compound. Soothe your weary muscles in your private jacuzzi after taking in the sights all day.



OLD TOWN 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$240 -
$2,755

ARTIST HOUSE: Located within the gated rooftop community of Duval Square, this 2 bedroom 2.5 bath with sleeper sofa and beautifully decorated, is perfectly located so that you can park your car in the private lot and walk downstairs to restaurants, specialty stores, attractions and nightlife of Old Town Key West. When you have had your fill, soak in the jacuzzi on your private deck.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$1,300 -
$2,610

CALYPSO: A beautiful 2 bedroom 2 bath second floor condominium, decorated with a Caribbean flair is located in Truman Annex, a gated community within Old Town Key West. Anything you want to do is within walking distance -- Duval Street, Sunset celebration, Fort Zachary Taylor State Park, bars, restaurants and shopping.



TRUMAN ANNEX 2 Bedroom Condo Key West, Fl 2 bedrooms
1.5 baths
$1,300 -
$2,610

BAHAMIAN REED: A luxury 2-bedroom 1.5 bath townhome located in the prestigious gated community of Truman Annex in walking distance of all the activities in Old Town Key West -- Fort Zachary Taylor State Park and beach, Duval Street and the nightly Sunset Celebration at Mallory Square, shopping, bars and restaurants.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

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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Showing homes 1 - 25 of 59