Key West Vacation Rentals

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Displaying 1 - 12 of 65 rentals matching your search criteria

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Old Town

Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Stock Island

Find serenity in this pleasant and spacious home with tons of Key West charm. Featuring an abundance of back yard space for lounging or entertaining, you will not want to leave this lovely retreat.

Pets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Pets Not AllowedWasher/DryerPoolGated Community

Old Town

Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.

Pets Not AllowedWasher/DryerPoolMonthly Rental

Stock Island

Coral Garden is a two bedroom town home in the quiet gated community of Coral Hammock located on Stock Island. Perfect for families or those who are working from home. Close to all that Key West has to offer.

Pets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

When a name says it all you know you have made the perfect choice for your Key West island escape.

Pets Not AllowedWasher/DryerPoolGated Community

Old Town

Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.

Pets Not AllowedWasher/DryerPoolGated CommunityMonthly Rental

Old Town

Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.

Pets Not AllowedWasher/DryerPoolMonthly Rental

Old Town

Stop searching, Conch Wind is the rental home in Key West you have been hunting for!

Pets Not AllowedWasher/DryerPoolGated Community

Ocean Side

Enjoy spectacular ocean views from this lovely rental!

ElevatorHot TubPets Not AllowedWasher/DryerGrillPoolGated Community

Old Town

Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.

Pets Not AllowedWasher/DryerGrillPoolGated Community

Old Town

Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle town home within easy walking distance to everything!

Pets Not AllowedWasher/DryerPool

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