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 - 6 of 6 rentals matching your search criteria
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Brisa Del Mar

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Enjoy spectacular ocean views from this lovely rental!

Casita de Catherine

Type

  • Cottage
Old Town
1 Bedroom
1 Bath
3 Guests

Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West. A welcoming outdoor space with a relaxing feel, this rental features a private hot tub and grill for outdoor entertaining.

Tradewinds

Type

  • Condominium
Ocean Side
3 Bedrooms
2 Baths
6 Guests

A quick jaunt across the street takes you to Key West’s longest beach. A few blocks away you’ll discover dining and shopping galore on famous Duval Street. A short bike ride and you're at the Historic Seaport.

Spa Oasis

Type

  • House
Stock Island
3 Bedrooms
2 Baths
6 Guests

Welcome to a golfer’s paradise at Spa Oasis!

Atlantic Paradise

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

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.

Papaya Place

Type

  • Condominium
Ocean Side
2 Bedrooms
2 Baths
6 Guests

Atlantic Ocean is just at your reach when staying at Papaya Place! You can almost hear the waves of the ocean!