Key West Vacation Rentals
You are here
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
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.
30 Day RentalPoolWasher/Dryer
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West.
Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.
30 Day RentalPoolGrillPets 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
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
1 Bedroom
2 Baths
2 Guests
If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
4 Guests
Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space.
30 Day RentalPoolGrillWasher/DryerPets Allowed
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
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
1.5 Baths
4 Guests
Located above the world-renowned Wyland Gallery of Key West, this roof top getaway is the ideal spot for the sophisticated, discerning traveler.
Daily - Weekly / Washer/Dryer
2 Bedrooms
1.5 Baths
4 Guests
Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.
30 Day RentalGrillWasher/Dryer
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.
30 Day RentalPoolGrillWasher/DryerPets Allowed
Pages
