Key West Vacation Rentals

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Displaying 1 - 12 of 41 rentals matching your search criteria

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Stock Island

This cozy 2 bedroom home is nestled in the center of the Key West Golf Club on a secluded lane.

Pets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

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

Pets AllowedWasher/DryerGrillPool

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

Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!

Outdoor ShowerPets AllowedWasher/DryerGrillPool

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

Stock Island

Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

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

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

View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Pets Not AllowedWasher/DryerGrillPoolGated Community

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

Old Town

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

Pets Not AllowedWasher/DryerGrillPoolMonthly Rental

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