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!
2 Bedrooms
2 Baths
6 Guests
Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
2 Bedrooms
1.5 Baths
4 Guests
Located above the world-renowned Wyland Gallery of Key West. Wyland Penthouse offers a fantastic front row seat overlooking the famous Duval Street from your private outdoor balcony.
Daily - Weekly / Washer/Dryer
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is a vacation rental home that you will come back to again and again
2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2.5 Baths
6 Guests
Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer!
Daily - Weekly / PoolWasher/DryerGated Community
5 Bedrooms
5.5 Baths
12 Guests
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!
Daily - Weekly / PoolGrillWasher/Dryer
2 Bedrooms
2 Baths
6 Guests
Imagine swimming in the Olympic size pool and enjoying a spectacular view of Atlantic Ocean at the same time!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
2 Bedrooms
1 Bath
4 Guests
Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space.
30 Day RentalPoolWasher/DryerPets Allowed
3 Bedrooms
2 Baths
6 Guests
This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops!
Daily - Weekly / PoolGrillWasher/DryerGated Community
3 Bedrooms
3.5 Baths
7 Guests
Luxury rental with all the amenities you can ask for, Bahama House might just be right right vacation rental for you!
Daily - Weekly / PoolGrillWasher/Dryer
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