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
3 Guests
Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops.
30 Day RentalPoolGrillPets AllowedPet Considered
2 Bedrooms
2.5 Baths
6 Guests
After a long day cool off in the private pool, enjoy cold Margarita on the covered porch and cook up some fresh catch on the grill! Welcome to your dream vacation home!
Daily - Weekly / PoolGrillWasher/DryerPets Allowedoutdoor showerfitness centergolftennisPet Considered
3 Bedrooms
3 Baths
8 Guests
Ideal for a family vacation or group of friends looking for a rental on a budget. Located very close to some great Key West restaurants this property is a steal!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityPets AllowedPet Considered
2 Bedrooms
1 Bath
4 Guests
Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
1.5 Baths
5 Guests
Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation!
Daily - Weekly / PoolGrillWasher/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 Allowedfitness centergolftennisPet Considered
2 Bedrooms
2.5 Baths
4 Guests
You are so close to the large community pool that you will be able to hear the waterfall in this beautifully landscaped area.
30 Day RentalPoolWasher/DryerGated Communityfitness centergolftennis
2 Bedrooms
2.5 Baths
6 Guests
For those looking for a cozy little getaway on a budget - Coral Garden is the asnwer!
Daily - Weekly / PoolGrillWasher/DryerGated Community
1 Bedroom
2 Baths
2 Guests
If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.
30 Day RentalPoolGrillWasher/DryerPets Allowedoutdoor showerPet Considered
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 AllowedPet Considered
2 Bedrooms
2 Baths
4 Guests
Ocean views from your wrap around balcony and the Olympic sized pool await you at this beautiful home.
30 Day RentalPoolWasher/DryerGated CommunityElevatorfitness centerpets not allowed
3 Bedrooms
2 Baths
6 Guests
Private home with large covered outdoor living area overlooking your private pool w/waterfall.
30 Day RentalPoolGrillWasher/DryerPets AllowedPet Considered
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