Key West Vacation Rentals

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Displaying 61 - 72 of 72 rentals matching your search criteria

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Old Town

Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!

Pets Not AllowedWasher/DryerPoolGated Community

Old Town

Casita de Catherine is a hidden gem! Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West.

Hot TubPets AllowedWasher/DryerGrill

Ocean Side

This great 2 bedroom, 2 bathroom, Key West condo located at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve.

ElevatorHot TubPets Not AllowedWasher/DryerGrillPool

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

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

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

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

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

Ocean Side

Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.

ElevatorHot TubPets Not 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

Stock Island

Welcome to your home away from home in Key West. This lovely town home is located in the Key West Golf Club Community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment.

Pets Not AllowedWasher/DryerGrillPoolGated CommunityMonthly Rental

Old Town

Settled in a small community in Old Town, only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental.

Pets Not AllowedGrillPoolGated Community

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