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!

Displaying 1 - 12 of 77 rentals matching your search criteria
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Beach House Condo

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.

Shipyard Treasure

Type

  • Condo
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.

Casa Grande

Type

  • Home
5 Bedrooms
5.5 Baths
12 Guests
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!

Paradise Place

Type

  • Condo
1 Bedroom
1 Bath
4 Guests
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach

Tradewinds

Type

  • Condo
3 Bedrooms
2 Baths
6 Guests
A quick jaunt across the street takes you to Key West’s longest beach. A few blocks away you’ll discover dining and shopping galore on famous Duval Street. A short bike ride and you're at the Historic Seaport.

La Casita

Type

  • Home
2 Bedrooms
1 Bath
4 Guests
The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street.

A Barefoot Retreat

Type

  • Condo
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.

Key West Casa

Type

  • Townhouse
3 Bedrooms
2 Baths
6 Guests
This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.

Boat House

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.

Sundown Refuge

Type

  • Condo
2 Bedrooms
2 Baths
5 Guests
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

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