Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 73 - 75 of 75 rentals matching your search criteria
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Key West Found

Type

  • Townhouse
Old Town
2 Bedrooms
2.5 Baths
6 Guests

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

Bahamian Reed

Type

  • Townhouse
Old Town
2 Bedrooms
1.5 Baths
5 Guests

Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.

A Barefoot Retreat

Type

  • Condominium
Old Town
2 Bedrooms
1 Bath
4 Guests

No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community. This two-bedroom, one bath, second floor condo will feel like your own tropical home the minute you walk through the door.

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