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
2.5 Baths
6 Guests
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
Daily - Weekly / PoolWasher/DryerGated Community
3 Bedrooms
4.5 Baths
8 Guests
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless private Conch home.
30 Day RentalPoolGrillWasher/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
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
2 Bedrooms
1.5 Baths
4 Guests
Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!
30 Day RentalGrillWasher/Dryer
1 Bedroom
1 Bath
2 Guests
As you step through the natural wooden gate onto the brick pathway, you will be embraced by this private garden oasis.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
6 Guests
Key West is all about the beach and the ocean! Located right by Smathers Beach, this tastefully decorated rental might just be the answer!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
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/DryerPets Allowed
1 Bedroom
1 Bath
2 Guests
NEWTON'S NEST (Monthly Rental)
30 Day RentalPoolWasher/Dryer
2 Bedrooms
2.5 Baths
6 Guests
Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle townhome within easy walking distance to everything!
Daily - Weekly / PoolWasher/DryerGated CommunityElevator
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
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