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
2.5 Baths
6 Guests
Just steps away from Harry Truman's "Little White House" you find your dream come true spacious vacation rental home
Daily - Weekly / PoolWasher/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
6 Bedrooms
5.5 Baths
14 Guests
With an unbeatable location, two pools and all top of the line appliances Duval Compound is a true find among vacation rental properties
Daily - Weekly / PoolGrillWasher/Dryerfitness centerpets not allowed
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 AllowedPet Considered
2 Bedrooms
1 Bath
4 Guests
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevatorfitness centertennispets not allowed
2 Bedrooms
2 Baths
4 Guests
It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool.
30 Day RentalPoolGrillWasher/DryerPets Allowedfitness centertennisPet Considered
2 Bedrooms
2.5 Baths
6 Guests
Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido!
Daily - Weekly / PoolGrillWasher/DryerPets Allowedoutdoor showerfitness centergolftennisPet Considered
2 Bedrooms
2 Baths
4 Guests
Located in a quiet community of Windward Park, only a short walk to Duval Street, with a large shared pool, Island Wind is a true gem in between our rentals
Welcome to a tropical sun drenched oasis in the heart of Old Town Key West.
Daily - Weekly / PoolGrillWasher/DryerGated Communitypets not allowed
3 Bedrooms
4 Baths
8 Guests
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.
The name says it all!
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals
A two-bedroom, two-bath condo in Truman Annex.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2.5 Baths
4 Guests
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you!
Daily - Weekly / PoolWasher/DryerGated Community
Pages
