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
2.5 Baths
4 Guests
A beautifully designed yet comfortable private home that you may never want to leave, only to go outside to your private pool and secluded space to hang out - that's the Verandah!
30 Day RentalPoolGrillWasher/Dryer
3 Bedrooms
2.5 Baths
6 Guests
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
1 Bath
4 Guests
Looking for the perfect home away from home? No need to look any further!
No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!
30 Day RentalGrillWasher/Dryer
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
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
2.5 Baths
4 Guests
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
1.5 Baths
4 Guests
Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Located right around the corner from Banana Cafe and Duval Street ,but still offering plenty of privacy, this cozy cottage with fully fenced yard makes a perfect rental for a small family or few friends trying to make the best of Key West!
Daily - Weekly / GrillWasher/DryerPets Allowed
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 Allowed
2 Bedrooms
1 Bath
4 Guests
Finding a perfect property for your family vacation is easier said than done, but this contemporary condo at Truman Annex might just be the one.
Daily - Weekly / PoolWasher/DryerGated Community
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