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!
2 Bedrooms
1 Bath
3 Guests
This perfect spot offers plenty of private outdoor space within walking distance of great restaurants and shops.
30 Day RentalPoolGrillPets Allowed
2 Bedrooms
1.5 Baths
4 Guests
For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the logical choice!
30 Day RentalPoolWasher/DryerGated CommunityPets 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.
At Easy Livin' the name says it all!
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2.5 Baths
6 Guests
The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.
Daily - Weekly / PoolGrillWasher/DryerGated Community
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
1 Bedroom
1 Bath
2 Guests
NEWTON'S NEST (Monthly Rental)
30 Day RentalPoolWasher/Dryer
1 Bedroom
1 Bath
2 Guests
Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This understated Truman Annex Condo is the place!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.
30 Day RentalPoolWasher/Dryer
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
1 Bath
4 Guests
Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2.5 Baths
6 Guests
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
Daily - Weekly / PoolWasher/DryerGated Community
3 Bedrooms
4.5 Baths
8 Guests
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.
30 Day RentalPoolGrillWasher/Dryer
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