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
2.5 Baths
6 Guests
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
In a small gated community this perfect cottage with a large private deck to allow all the privacy you would need to grill, dine and lounge.
30 Day RentalPoolGrillWasher/DryerGated Community
1 Bedroom
2 Baths
2 Guests
This unique 1 bedroom, 2 bath cottage is about to become your home away from home!
Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE!
30 Day RentalPoolWasher/Dryerfitness centergolftennispets not allowed
1 Bedroom
1.5 Baths
4 Guests
Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental
Daily - Weekly / PoolGrillGated Communityfitness centergolftennispets not allowed
2 Bedrooms
1 Bath
5 Guests
Enjoy your morning coffee, afternoon cocktail or freshly grilled fresh catch on the outside patio when taking a break from exploring Key West!
Daily - Weekly / PoolGrillWasher/DryerGated Communityfitness centergolftennis
2 Bedrooms
1.5 Baths
4 Guests
Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport.
30 Day RentalGrillWasher/Dryerfitness centergolftennis
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!
Daily - Weekly / PoolWasher/DryerGated CommunityElevatorfitness centergolfpets not allowed
2 Bedrooms
1 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.
30 Day RentalPoolWasher/Dryer
2 Bedrooms
2.5 Baths
6 Guests
This beautiful vacation rental is located in the heart of Old Town, close to everything Key West has to offer!
Daily - Weekly / PoolWasher/DryerGated CommunityElevatorfitness centergolfpets not allowed
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
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
1.5 Baths
6 Guests
Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off.
30 Day RentalPoolWasher/DryerGated CommunityPets AllowedPet Considered
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