Key West Vacation Rentals

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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.

Pets Not AllowedWasher/DryerPoolGated Community

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

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

Old Town

Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle town home within easy walking distance to everything!

Pets Not AllowedWasher/DryerPool

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

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.

Pets AllowedWasher/DryerGrillPoolMonthly Rental

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

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

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

Old Town

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

Pets AllowedWasher/DryerGrillPoolMonthly Rental

Old Town

Searching for an affordable monthly vacation rental in the heart of Key West? Do you plan on spending most of your time enjoying all that Key West has to offer and seeing what if feels like to really live like a local? Then tune into Windchime!

Pets Not AllowedMonthly Rental

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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