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

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

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Old Town

Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.

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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

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

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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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

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

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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

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

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

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.

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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/DryerGrillPoolGated Community
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