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Showing 1-25 of 66 Vacation Rentals

William's Loft

Key West, Florida, United States
$2,500
1-305-296-6996
cottage 2 BR 1 BA Sleeps 4

Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. The cottage is... 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

cottage 2 BR 2 BA Sleeps 4

Casa MaƱana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two... more

Waterfront Two-Bedroom Suite

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

Upgrade to luxury with a master king room, second queen room, living room, and water view balcony. Breathe the salt air from a beautiful two-bedroom... more

Ann Street Tranquility

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

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

Duval Roost

Key West, Florida, United States
house 3 BR 4 BA Sleeps 6

This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a private lane. Enter the property through a secure... more

Townhomes on Windsor #4

Key West, Florida, United States
townome 3 BR 4 BA Sleeps 6

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town... more

Louisa House

Key West, Florida, United States
house 4 BR 4 BA Sleeps 10

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually... more

Showing 1-25 of 66 Vacation Rentals

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