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 1 - 12 of 56 rentals matching your search criteria
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Old Town

Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

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Old Town

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

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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.

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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.

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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.

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Old Town

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

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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.

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Old Town

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

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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!

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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

**** 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!

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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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