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

Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.

Pets Not AllowedWasher/DryerPoolMonthly Rental
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Old Town

Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!

Pets Not AllowedWasher/DryerPoolGated Community
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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
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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

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

When a name says it all you know you have made the perfect choice for your Key West island escape.

Pets Not AllowedWasher/DryerPoolGated Community
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Old Town

A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.

Pets AllowedPets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly 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

“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.

Pets Not AllowedWasher/DryerPoolGated Community
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Old Town

A beautiful three-story home with private pool, off street parking, and attractive decor, Ecco Domani is a wonderful Key West escape that you will want to come home to year after year.

Pets AllowedWasher/DryerGrillPoolMonthly Rental
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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
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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
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