Key West Vacation Rentals

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Displaying 61 - 72 of 72 rentals matching your search criteria

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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

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

Located in Bahama Village, a quaint neighborhood in Old Town Key West, this beautifully renovated conch home is a romantic island getaway. This rental is a guest house situated in the back yard of a private residence.

Pets Not AllowedWasher/DryerPoolMonthly Rental

Stock Island

Coral Breeze is a two bedroom town home located in the gated community at the Key West Golf Club on Stock Island. This modern and comfortable home is perfect for a couple or small family looking to stay for a month in Key West.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

Your perfect escape to Key West awaits you in the Land of Love.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.

Pets Not AllowedWasher/DryerGrillPoolGated Community

Old Town

The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.

Pets Not AllowedWasher/DryerGrillMonthly Rental

Mid Town

Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.

Pets AllowedWasher/DryerGrillPoolMonthly 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 on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Pets Not AllowedWasher/DryerPoolGated 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

Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!

Pets Not AllowedWasher/DryerPool

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