Key West Vacation Rentals

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Displaying 1 - 12 of 72 rentals matching your search criteria

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Old Town

Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!

Outdoor ShowerPets AllowedWasher/DryerGrillPool

Old Town

View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Pets Not AllowedWasher/DryerGrillPoolGated Community

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

Stock Island

Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story town home located in the private gated community of Coral Hammock on Stock Island.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Ocean Side

Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.

ElevatorHot TubPets Not AllowedWasher/DryerGrillPool

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

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

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

Pets Not AllowedWasher/DryerGrillPoolGated Community

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

Stock Island

Situated in the gated community at the Key West Golf Club, Wind Swept is a perfect retreat for a small family or two couples looking for a monthly rental.

Pets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Pets Not AllowedWasher/DryerPoolGated Community

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