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!
1 Bedroom
2 Baths
2 Guests
Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.
30 Day RentalPoolWasher/Dryer
2 Bedrooms
1 Bath
5 Guests
Looking for a peaceful retreat yet close to everything? Ideally located on Southard Street, within walking distance to the beach at Fort Zachary Taylor State Park, Duval Street and Mallory Square, Bayview Harbor is the spot you’ve been looking for.
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
1 Bath
4 Guests
You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods.
Daily - Weekly / PoolGrillWasher/DryerGated Community
3 Bedrooms
2 Baths
5 Guests
Welcome to a golfer’s paradise at Spa Oasis!
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
1 Bedroom
1 Bath
4 Guests
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
2 Bedrooms
2.5 Baths
6 Guests
Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle townhome within easy walking distance to everything!
Daily - Weekly / PoolWasher/DryerGated CommunityElevator
2 Bedrooms
1 Bath
4 Guests
Be one of the first to stay in this totally updated vacation home in the popular gated community of the Truman Annex. This 2-bedroom 1 bath second floor Shipyard condo has new floors, fresh paint, all new furnishings, artwork, linens and towels.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.
Daily - Weekly / PoolWasher/DryerGated Community
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
2 Bedrooms
2 Baths
4 Guests
Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
5 Guests
Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Nautical Dreams is the perfect spot for whatever you desire - parties or peace and quiet in a Key West vacation home.
30 Day RentalPoolGrillWasher/DryerGated Community
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