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Showing 26-47 of 47 Vacation Rentals

Coconut Cabana

Key West, Florida, United States

An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored... more

House 3 BR 2 BA Sleeps 6

Southard Street - Queen Conch

Key West, Florida, United States

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat.... more

House 4 BR 4 BA Sleeps 14

La Brisa 405E Sea Orchid

Key West, Florida, United States

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South... more

Condo 2 BR 2 BA Sleeps 4

Albury Bungalow

Key West, Florida, United States

A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one bedroom, one bathroom house also boasts a separate cottage bedroom with it's own bathroom. Lounge on the sunny deck around the heated pool or... more

Bungalo 2 BR 2 BA Sleeps 4

Louisa House

Key West, Florida, United States

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom,... more

House 4 BR 4 BA Sleeps 10

La Brisa #206E - Brisa Del Mar

Key West, Florida, United States

This unit is designed to catch the ocean breeze, with the exterior walkway leading to your front door and opening up to the view of the balcony beyond the interior. Featuring two large bedrooms and 2 baths, the interiors provide ample space for a... more

Condo 2 BR 2 BA Sleeps 6

La Brisa #302E Tropical Tranquility

Key West, Florida, United States

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South... more

Condo 1 BR 1 BA Sleeps 2

Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The... more

Condo 1 BR 1 BA Sleeps 4

Beach Club #201

Key West, Florida, United States

This 2 bedroom 2 bath unit features a huge oceanfront balcony accessed from both the living/dining area and master bedroom. It has central heat/air, cable TV, washer/dryer, well-equipped kitchen, 2 baths, security entry and elevator access. There is... more

Condo 2 BR 2 BA Sleeps 6

Duval Square Castaway

Key West, Florida, United States

In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch,... more

Town Home 2 BR 2 BA Sleeps 6

Paradise Harbor Retreat

Key West, Florida, United States

Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best of Florida Keys style, this spacious townhome has 3 bedrooms, 3.5 baths and is situated in a quiet Meadows... more

Town Home 3 BR 4 BA Sleeps 8

Pete's West Cottage

Key West, Florida, United States

This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior with the clean lines of a contemporary home. Each... more

Cottage 2 BR 1 BA Sleeps 4

Beach Club #103

Key West, Florida, United States

Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom unit features a large oceanfront balcony accessed from both the living/dining area and master bedroom. The unit features central heat/air, WIFI, cable TV, washer/dryer, well... more

Condo 2 BR 2 BA Sleeps 6

Casa Atlantica One Bedroom

Key West, Florida, United States

Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled with a mixture of custom made furnishings and unusual objects from all parts of the globe, this... more

Condo 1 BR 1 BA Sleeps 2

Newton Street Hideaway

Key West, Florida, United States

The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is... more

Bungalo 1 BR 2 BA Sleeps 4

South St. Cottage

Key West, Florida, United States

A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large... more

Cottage 2 BR 2 BA Sleeps 6

2 Master suites each with a king bed, The 3rd bedroom has 2 twin beds and there is a queen sleeper sofa in the living room. Large private balcony opens off of all the rooms.... more

Condo 3 BR 3 BA Sleeps 8

Ann Street Tranquility

Key West, Florida, United States

This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces. Across from the Curry Mansion and Old City Hall, around the corner from Duval Street and offering... more

Cottage 1 BR 1 BA Sleeps 2

Villa Tropicale

Key West, Florida, United States

Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are... more

House 4 BR 4 BA Sleeps 8

Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away... more

Cottage 2 BR 2 BA Sleeps 4

Ann Street Cottage

Key West, Florida, United States

This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces. Across from the Curry Mansion and Town Hall, around the corner from Duval Street and offering 'walk to... more

Cottage 1 BR 2 BA Sleeps 4

President's Walk

Key West, Florida, United States

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 beach, this gated community offers lush gardens and a beautiful community pool at your doorstep. For... more

House 2 BR 2 BA Sleeps 4

Showing 26-47 of 47 Vacation Rentals

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