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Key West Vacation Rentals

Book Key West’s Best Vacation Rentals

Rent Key West Vacations manages the best Key West Vacation Rentals. For over twenty years, we’ve connected with Key West property owners and represented many of Key West’s most historic homes. On this page, you'll find properties with private pools and ocean views. Each rental is unique, so you can easily discover the right place for your group. Browse Cottages, Beach Condos, and Historic Homes at the center of Old Town Key West.

Plan Your Dream Key West Vacation!

The following results matched your search criteria.

List View

CasaBella @ Duval Square

Condo
Bedrooms 2
2.5 Bathrooms

Located just steps from famous Duval street, this two-story town home is located in quaint, cobble stoned Duval Square. You are within the heart of the historic district and can walk almost everywhere. Although close to Duval, the home is a quiet escape from the hustle bustle.

Louisa House

House
Bedrooms 4
3.5 Bathrooms

An absolutely perfect location, just a half a block off Duval Street and within walking distance to amazing restaurants, turquoise beaches and the Southernmost Point in the United States. Louisa House has it all for the perfect Key West vacation.

Ashe Splashe

House
Bedrooms 3
3 Bathrooms

28 DAY MINIMUM RENTAL

From the owners of South of Frances, here is another beautiful, historic restoration project. This lovingly restored home is ready for guests following a complete redo! The attention to detail and master craftsmanship can be seen everywhere in this beautiful home.

Heavenly Zen

House
Bedrooms 4
3.5 Bathrooms

Just a few blocks from Higgs Beach sits Heavenly Zen.

This four-bedroom home was recently renovated in February of 2019. Enter the home through the deep front porch— perfect for relaxing with a cocktail and chatting with the neighbors.

Pete's Cottages

House
Bedrooms 4
2 Bathrooms

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall. 

Dreaming on Duval

House
Bedrooms 5
4.5 Bathrooms

Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval!

Catherine House

House
Bedrooms 2
2 Bathrooms

This charming Key West cottage is just a short walk to a selection of great restaurants, art galleries, and shopping.

Shipyard Palms

Condo
Bedrooms 2
1.5 Bathrooms

In the heart of old town Key West, nestled within the secluded and lush community of private homes and condominiums of Truman Annex, this Shipyard Condominium has convenient access to both the gorgeous Fort Zachary State Park Beach and historic old town Key West. 

Casa Atlantica One Bedroom

Condo
One Bedroom
One Bathroom

Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name:  a home perched on the very edge of the turquoise waters of the Atlantic.  Located on the quiet end of a waterfront townhome community, this property features simply the best views you will f

Beach Club #204

Condo
Bedrooms 2
2 Bathrooms

Unique oceanfront living only 65 feet from the Atlantic!

The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water.  The breathtaking view can be seen as soon as you enter the unit.  

Map View