Key West Vacation Rentals

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Displaying 25 - 36 of 72 rentals matching your search criteria

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Stock Island

Located in the Sanctuary of the gated community in the Key West Golf Club, this spacious single-family home welcomes you to the laid-back island life with the ease of everything on one floor.

Hot TubPets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly 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

Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.

Pets Not AllowedWasher/DryerGrillMonthly 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

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

Stock Island

Beautifully decorated spacious 3 bedroom, 3 bathroom with off-street parking for 2 vehicles -- a rare commodity in Key West!

Pets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly 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

Ocean Side

This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean.

Pets Not AllowedWasher/DryerPoolGated CommunityMonthly 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

Old Town

Your perfect escape to Key West awaits you in the Land of Love.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

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.

Pets Not AllowedWasher/DryerGrillPoolGated Community

Old Town

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

Pets Not AllowedWasher/DryerPoolMonthly Rental

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