Key West Vacation Rentals

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Displaying 13 - 24 of 72 rentals matching your search criteria

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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

**** 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

Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.

Pets Not AllowedWasher/DryerGrillMonthly Rental

Old Town

Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.

Pets Not AllowedWasher/DryerPoolMonthly 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

Ocean Side

Enjoy spectacular ocean views from this lovely rental!

ElevatorHot TubPets Not AllowedWasher/DryerGrillPoolGated Community

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

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

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.

Pets Not AllowedWasher/DryerGrillMonthly Rental

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/DryerPoolGated Community

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

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