Key West Vacation Rentals

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Displaying 37 - 48 of 72 rentals matching your search criteria

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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

Old Town

Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!

Pets Not AllowedWasher/DryerPool

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

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

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

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

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Pets Not AllowedWasher/DryerPoolGated Community

Old Town

Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.

Pets Not AllowedWasher/DryerPoolGated CommunityMonthly Rental

Old Town

Situated on Key West's historical Whitehead Street is Spanish Lime Cottage, appropriately named for one of the lime trees in the back yard. Whitehead runs parallel to Duval Street and is right in the heart of Old Town, Key West.

Pets AllowedWasher/DryerGrillMonthly 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

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

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