Old Town Key West Rentals

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Our Old Town Key West rentals include both short term and monthly rentals ranging from modest studio cottages to large 5 and 6 bedroom homes. You'll find rentals in some of Old Town's most popular communities including Truman Annex, Duval Square and Windward Park. We even have pet-friendly rentals in Old Town.

Old Town Key West, on the western half of the island, is filled with rich history and contains many of our most popular attractions including the Hemingway House, Southernmost Point, Key West Lighthouse, Fort Zachary Taylor State Park, Museum of History, Mallory Square and the famous Duval Street.

Search by travel dates and filter by amenities to quickly see availability and pricing. Don't hesitate to reach out to our experienced local team with questions or for help finding and booking the perfect rental in Old Town Key West!

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Displaying 37 - 48 of 56 rentals matching your search criteria
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Old Town

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

Recently remodeled, tastefully decorated. This rental is hard to beat!

Pets Not AllowedWasher/DryerPoolGated Community
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Old Town

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

Pets Not AllowedWasher/DryerPoolGated Community
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Old Town

After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home!

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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
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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
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Old Town

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

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental
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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
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Old Town

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

Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!

Pets Not AllowedWasher/DryerPoolGated Community
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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
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Old Town

Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!

Pets AllowedWasher/DryerGrillPoolMonthly Rental
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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.

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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.

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