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 85 - 92 of 92 rentals matching your search criteria
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Cayo Hueso Sunshine

Type

  • Home
2 Bedrooms
3 Baths
6 Guests
French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool.

Windchime

0.5 Bedrooms
1 Bath
2 Guests
Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime!

Tropical Dreaming

Type

  • Home
2 Bedrooms
2.5 Baths
6 Guests
Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido!

Shipyard Treasure

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Finding a perfect property for your family vacation is easier said than done, but this beautiful apartment might just be the one.

Contemporary Condo at Truman Annex - Walk to Beach/Duval Street

Lavender Jungle

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
This gorgeous apartment is located in one of Key West's most attractive, quiet, and convenient neighborhoods, Truman Annex, close to many attractions and also Fort Zachary Taylor Beach

La Casita

2 Bedrooms
1 Bath
4 Guests
LOCATION YOU CAN NOT BEAT! Located right in the heart of Old Town yet on a quiet lane, only steps to Duval Street, Blue Heaven and many other restaurants and little boutiques!

Island Wind

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
Located in a quiet community of Windward Park, only a short walk to Duval Street, with a large shared pool, Island Wind is a true gem in between our rentals

Welcome to a tropical sun drenched oasis in the heart of Old Town Key West.

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