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
This charming, clean and nicely decorated vacation rental home is located in Coral Hammock, one of Key West newest communities, very close to restaurants, boating and water adventure!
Daily - Weekly / PoolGrillWasher/DryerGated Community
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 CommunityElevatorfitness centergolfpets not allowed
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own deck or balcony in the Truman Annex’s most prestigious building
Daily - Weekly / PoolGrillWasher/DryerGated Community
3 Bedrooms
2 Baths
6 Guests
Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.
30 Day RentalPoolGrillWasher/DryerPets AllowedPet Considered
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!
Daily - Weekly / PoolWasher/DryerGated Community
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 AllowedPet Considered
3 Bedrooms
3 Baths
6 Guests
Beautifully decorated and spacious home in the community of Truman Annex is awaiting for you!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Imagine swimming in the Olympic size pool and enjoying a spectacular view of Atlantic Ocean at the same time!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevatorfitness centergolfpets not allowed
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
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 Communityfitness centergolftennispets not allowed
2 Bedrooms
1 Bath
4 Guests
Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends
Daily - Weekly / PoolWasher/DryerGated Communityfitness centertennis
3 Bedrooms
2.5 Baths
7 Guests
Location, location, location! Practically overlooking famous Duval Street from large upstairs deck!
Daily - Weekly / PoolGrillWasher/Dryerfitness centertennispets not allowed
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