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Showing 1-25 of 65 Vacation Rentals

Bahamian Reed

Key West, Florida, United States
$250
1-305-296-6996
townhome 2 BR 1 BA Sleeps 5

Bahamian Reed is a two-bedroom, one-and-a-half bathroom townhome located in Truman Annex in Old Town Key West near all the reasons you came to Key... more

Beach House Condo

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 4

Beach House Condo has the perfect back deck to sip a cafe con leche in the morning or read a book in the afternoon. The property has an open floor... more

Duval Breeze

Key West, Florida, United States
house 2 BR 2 BA Sleeps 6

Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval Street in Old Town Key West and a few blocks from the... more

Key West Found

Key West, Florida, United States
townome 2 BR 2 BA Sleeps 6

Key West Found is a striking 2 bedroom, 2.5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3-story... more

Flagler Station

Key West, Florida, United States
$3,200
1-305-296-6996
house 3 BR 2 BA Sleeps 8

Flagler Station is a recently remodeled, refurbished and re-furnished rental that features a spacious living room and dining area, allowing plenty of... more

Shipyard Treasure

Key West, Florida, United States
condo 2 BR 1 BA Sleeps 4

Decorated in casual contemporary style, Shipyard Treasure is centrally located in the Truman Annex, as well as within quick walking distance to all... more

Sunshine on the Rocks

Key West, Florida, United States
$3,500
1-305-296-6996
condo 2 BR 2 BA Sleeps 6

This stunning townhome has spectacular waterfront views of the bay with an ideal location on a secluded peninsula. Sunshine On The Rocks is the... more

Conch Wind

Key West, Florida, United States
house 2 BR 2 BA Sleeps 4

This two-story Conch Style townhome is nestled in a quiet, secure compound, and features plenty of space, beautifully furnished with all attention... more

Casa on Casa

Key West, Florida, United States
$8,500
1-305-296-6996
house 4 BR 3 BA Sleeps 8

So simple yet elegant, intimate yet spacious, Casa on Casa offers a unique Key West experience that will linger in your memory for years to come. As... more

Bloom'n Paradise

Key West, Florida, United States
house 4 BR 4 BA Sleeps 8

Relax in luxury in this beautiful Truman Annex private vacation home in the Florida Keys. Bloom'n Paradise features three bedrooms and three bathrooms... more

Sunset Celebration

Key West, Florida, United States
$1,900
1-305-296-6996
condo 2 BR 1 BA Sleeps 4

Sunset Celebration is a two-bedroom, one-bathroom Shipyard condo located in Truman Annex. New floors, fresh paint, all new furnishings, artwork,... more

Casa Grande

Key West, Florida, United States
$6,175
1-305-296-6996
house 5 BR 5 BA Sleeps 12

Casa Grande was built for hosting large gatherings of family and friends. A private home with an abundance of space for everyone to relax in privacy... more

Papaya Place

Key West, Florida, United States
$300
1-305-296-6996
condo 2 BR 2 BA Sleeps 6

Papaya Place is a great 2-bedroom, 2-bath waterfront Key West rental condo at 1800 Atlantic Condominiums that offers a wonderful relaxing garden view... more

Tranquility

Key West, Florida, United States
cottage 1 BR 1 BA Sleeps 4

Fabulous artwork, fun collectibles, beautiful stained glass all give Tranquility the unique feel that keeps bringing visitors back to Key West. As you... more

Bahama House

Key West, Florida, United States
$595
1-305-296-6996
house 3 BR 3 BA Sleeps 8

Totally gorgeous, Bahama House is conveniently located on a quiet street in the heart of Old Town Key West around the corner from the fabulous shops,... more

Tropical Dreaming

Key West, Florida, United States
$345
1-305-296-6996
house 2 BR 2 BA Sleeps 6

A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of both worlds while... more

Bogey's Retreat

Key West, Florida, United States
$2,100
1-305-296-6996
townome 2 BR 1 BA Sleeps 6

Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows... more

Crowner's Jewel

Key West, Florida, United States
$450
1-305-296-6996
house 2 BR 2 BA Sleeps 6

Experience the finest in vacation home rentals in Key West Florida when you stay at Crowner's Jewel. This rental features lots of space for a family... more

President's Walk

Key West, Florida, United States
house 2 BR 2 BA Sleeps 4

President’s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minutes from Fort Zachary Taylor State Park and its... more

Villa Paradiso

Key West, Florida, United States
house 3 BR 3 BA Sleeps 8

This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three... more

Southard Queen Conch Suite

Key West, Florida, United States
house 2 BR 2 BA Sleeps 6

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation... more

Casa de Cuba

Key West, Florida, United States
cottage 3 BR 2 BA Sleeps 6

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval... more

Ann Street Cottage

Key West, Florida, United States
cottage 1 BR 2 BA Sleeps 4

This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.... more

Vista Fresco

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 6

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400... more

Casa Atlantica One Bedroom

Key West, Florida, United States
condo 1 BR 1 BA Sleeps 2

Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled... more

Showing 1-25 of 65 Vacation Rentals

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