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 13 - 24 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.

Pets Not AllowedWasher/DryerPoolGated Community
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Old Town

The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.

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Old Town

Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.

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Old Town

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

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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.

Pets Not AllowedWasher/DryerPoolMonthly Rental
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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

Key Lime Pie is a private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.

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Old Town

Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.

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Old Town

Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.

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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

**** 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!

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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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