Key West Vacation Rentals

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Displaying 61 - 72 of 72 rentals matching your search criteria

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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

Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!

Pets Not AllowedWasher/DryerGrillMonthly Rental

Old Town

Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.

Pets Not AllowedWasher/DryerGrillPoolMonthly Rental

Old Town

Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.

Pets Not AllowedWasher/DryerGrillMonthly Rental

Old Town

Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home with a shared pool on property.

Pets AllowedGrillPoolGated CommunityMonthly Rental

Old Town

Enjoy a carefree vacation in 2 bedroom 1.5 bath, 2-story town home, located on Southard Court in the Truman Annex, downtown Key West. This home is situated right in front of the community pool.

Pets Not AllowedWasher/DryerGrillPoolGated Community

Old Town

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

Pets Not AllowedWasher/DryerGrillPoolGated Community

Ocean Side

This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean.

Pets Not AllowedWasher/DryerPoolGated CommunityMonthly Rental

Old Town

Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.

Pets AllowedWasher/DryerGrillPoolMonthly Rental

Old Town

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

Pets Not AllowedWasher/DryerPoolGated Community

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

Old Town

Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

Pets Not AllowedWasher/DryerPoolGated Community

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