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!
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 CommunityTennisPets Not Allowed
1 Bedroom
1 Bath
2 Guests
NEWTON'S NEST (Monthly Rental)
30 Day RentalPoolWasher/Dryer
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
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
Looking for the perfect home away from home? No need to look any further!
Step into this fantastic condo and the first thing you'll want to do is take off your shoes; feels just like home.
Daily - Weekly / PoolWasher/DryerGated CommunityFitness CenterGolfTennis
2 Bedrooms
2 Baths
4 Guests
The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops!
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
1.5 Baths
4 Guests
Perfect view from your screened porch to watch golfers play the first hole on the Rees Jones designed Key West Golf Course.
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.
30 Day RentalPoolGrillWasher/Dryer
1 Bedroom
2 Baths
2 Guests
This unique 1 bedroom, 2 bath cottage is about to become your home away from home!
Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE!
30 Day RentalPoolWasher/DryerFitness CenterGolfTennisPets Not Allowed
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
2 Bedrooms
1.5 Baths
6 Guests
Screened porches up and down for you to enjoy the the extra living space in this lovely townhome.
30 Day RentalPoolGrillWasher/DryerGated Community
1 Bedroom
1 Bath
4 Guests
Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets AllowedFitness CenterGolfTennisPet Considered
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