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 RentalPoolGrillWasher/Dryer
3 Bedrooms
3 Baths
6 Guests
Feel the tropical allure of this spacious home in the center-of-it-all community of the historic Truman Annex!
Daily - Weekly / PoolWasher/DryerGated Community
1 Bedroom
1 Bath
2 Guests
NEWTON'S NEST (Monthly Rental)
30 Day RentalPoolWasher/Dryer
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 / PoolGrillWasher/DryerGated CommunityElevator
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
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
2 Bedrooms
2.5 Baths
6 Guests
After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home!
Daily - Weekly / PoolGrillWasher/DryerPets Allowed
2 Bedrooms
2.5 Baths
4 Guests
This spacious home with a large outside deck is tucked away on a quiet lane of Truman Annex, yet only a short walk to all attractions.
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
2 Bedrooms
1.5 Baths
5 Guests
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2.5 Baths
4 Guests
A beautifully designed yet comfortable private home that you may never want to leave, only to go outside to your private pool and secluded space to hang out - that's the Verandah!
30 Day RentalPoolGrillWasher/Dryer
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?
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
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