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 1 - 7 of 7 rentals matching your search criteria
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Wind Swept

Type

  • Townhouse
2 Bedrooms
1.5 Baths
6 Guests
Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. All that and much more awaits you at Windswept!

A Little Slice Of Paradise

Type

  • Townhouse
2 Bedrooms
1.5 Baths
5 Guests
Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.