Key West Vacation Rentals

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Displaying 25 - 36 of 47 rentals matching your search criteria

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Old Town

Perfect for large families or groups of friends, this property offers great amenities including a private pool, open floor plan, 2 kitchens and a large laundry room, right downtown Key West.

Outdoor ShowerPets Not AllowedWasher/DryerGrillPool

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

Casita de Catherine is a hidden gem! Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West.

Hot TubPets AllowedWasher/DryerGrill

Old Town

Situated on Key West's historical Whitehead Street is Spanish Lime Cottage, appropriately named for one of the lime trees in the back yard. Whitehead runs parallel to Duval Street and is right in the heart of Old Town, Key West.

Pets AllowedWasher/DryerGrillMonthly 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

Mid Town

Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.

Pets AllowedWasher/DryerGrillPoolMonthly 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

This spacious home with a large outside deck is tucked away on a quiet lane in the Truman Annex, yet only a short walk to all attractions.

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

Welcome to your home away from home in Key West. This lovely town home is located in the Key West Golf Club Community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment.

Pets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

Settled in a small community in Old Town, only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental.

Pets Not AllowedGrillPoolGated Community

Stock Island

Located in the Sanctuary of the gated community in the Key West Golf Club, this spacious single-family home welcomes you to the laid-back island life with the ease of everything on one floor.

Hot TubPets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

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