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
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
5 Guests
Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Private cottage that has all the amenities you would require for your stay, private pool, outdoor space for lounging, grill and dining.
One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
4 Guests
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
With an elegant design Leeward Isle Key West Retreat offers a small but luxurious retreat.
Daily - Weekly / PoolWasher/DryerGated Community
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
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 Allowed
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
3 Bedrooms
2 Baths
8 Guests
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.
30 Day RentalPoolGrillWasher/Dryer
2 Bedrooms
2.5 Baths
6 Guests
Located in Duval Square, rooftop community which is just off Duval Street, easy walking distance to it all! You do not even need a car!
Daily - Weekly / PoolWasher/DryerGated CommunityElevator
2 Bedrooms
2 Baths
5 Guests
Enjoy breathtaking sunsets with a glass of wine from your own private porch
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.
Daily - Weekly / PoolGrillWasher/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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