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!
3 Bedrooms
3 Baths
8 Guests
Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityPets Allowed
2 Bedrooms
2.5 Baths
6 Guests
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!
Daily - Weekly / PoolWasher/DryerGated CommunityElevator
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
1 Bedroom
1 Bath
2 Guests
NEWTON'S NEST (Monthly Rental)
30 Day RentalPoolWasher/Dryer
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
3 Bedrooms
2.5 Baths
6 Guests
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.
30 Day RentalPoolGrillWasher/DryerPets Allowed
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
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
2 Bedrooms
1.5 Baths
4 Guests
Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport.
30 Day RentalGrillWasher/Dryer
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 Baths
6 Guests
Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
3 Bedrooms
4.5 Baths
8 Guests
In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point.
30 Day RentalPoolGrillWasher/Dryer
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