Key West Vacation Rentals

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Displaying 13 - 24 of 65 rentals matching your search criteria

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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/DryerPoolGated 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

Perfect for large families or groups of friends, this property offers great amenities including a private pool, open floor plan, 2 kitchens and a large laundry room, right downtown Key West.

Outdoor ShowerPets Not AllowedWasher/DryerGrillPool

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

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!

Pets Not AllowedWasher/DryerPoolGated 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

Stock Island

Coral Breeze is a two bedroom town home located in the gated community at the Key West Golf Club on Stock Island. This modern and comfortable home is perfect for a couple or small family looking to stay for a month in Key West.

Pets AllowedWasher/DryerGrillPoolGated CommunityMonthly 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

Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!

Pets AllowedWasher/DryerGrillPoolMonthly Rental

Mid Town

Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.

Pets AllowedWasher/DryerGrillPoolMonthly Rental

Mid Town

Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.

Pets AllowedWasher/DryerGrillPoolMonthly Rental

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