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

Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.

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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

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

This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

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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

Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.

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Old Town

The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.

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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

Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!

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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

**** 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

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.

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Old Town

It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.

Pets Not AllowedWasher/DryerGrillPoolGated Community
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