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
1 Bath
4 Guests
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.
30 Day RentalPoolWasher/Dryer
2 Bedrooms
2.5 Baths
4 Guests
Steps away from the large lagoon style pool surrounded w/lush tropical landscape.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
2 Bedrooms
2 Baths
4 Guests
Leeward Isle Key West Retreat – Location is everything! A hidden gem in the heart of Old Town Key West.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.
Daily - Weekly / PoolWasher/DryerGated Community
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
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
3 Bedrooms
3 Baths
8 Guests
Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityPets Allowed
2 Bedrooms
2 Baths
6 Guests
Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
0.5 Bedrooms
1 Bath
2 Guests
Great location, great price! Osprey is the perfect getaway rental for a couple who wants to enjoy everything Key West has to offer!
Daily - Weekly / PoolGated Community
1 Bedroom
2 Baths
2 Guests
Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
5 Guests
Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals
A two-bedroom, two-bath condo in Truman Annex.
Daily - Weekly / PoolWasher/DryerGated Community
3 Bedrooms
2 Baths
6 Guests
Private home with large covered outdoor living area overlooking your private pool w/waterfall.
30 Day RentalPoolGrillWasher/DryerPets Allowed
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