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
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
3 Bedrooms
2 Baths
5 Guests
Welcome to a golfer’s paradise at Spa Oasis!
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
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
4 Guests
Nautical Dreams is the perfect spot for whatever you desire - parties or peace and quiet in a Key West vacation home.
30 Day RentalPoolGrillWasher/DryerGated Community
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
3 Bedrooms
2 Baths
8 Guests
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2.5 Baths
6 Guests
Rooftop community just steps away from Duval Street to great restaurants, shopping and entertainment.
The pool will be completely shut down during July 8-19 due to pool resurfacing and repair of pool skimmers
30 Day RentalPoolWasher/DryerGated CommunityElevatorPets Allowed
2 Bedrooms
2.5 Baths
6 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 events.
Daily - Weekly / PoolGrillWasher/DryerGated Community
1 Bedroom
1 Bath
4 Guests
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
5 Guests
It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.
Daily - Weekly / PoolGrillWasher/DryerGated Community
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 Allowed
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