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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

Colony Sunset Suite

Condo
One Bedroom
One Bathroom

Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat.  Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art.

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

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.

Townhomes on Windsor #3

Villa
Bedrooms 3
3.5 Bathrooms

Once you enter this newly renovated and professionally decorated oasis…your vacation begins. This property has been created to meet your every need. The location is simply perfect: just three short blocks from Duval and tucked away on a quiet lane so you can choose your level of activity.

Sanctuary on Simonton

Condo
Bedrooms 2.5
3 Bathrooms

28 DAY MINIMUM- Dogs allowed, with restrictions

Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect extended-stay getaway.

Havana Lane

House
Bedrooms 2
2 Bathrooms

Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends.

La Brisa #206E - Brisa Del Mar

Condo
Bedrooms 2
2 Bathrooms

Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential condominium complex is situated opposite the largest beach on the island, while offering all the amenities of a resort hotel.

Duval Square Penthouse

Condo
Bedrooms 4
4.5 Bathrooms

This huge penthouse condo, located just steps from the action of Duval Street, has been recently upgraded. This four-bedroom, 4.5 bath condo is in the heart of the action at Duval Square, a charming brick-paved and tree-lined courtyard just south of Truman Avenue.

Duval Square Courtyard Condo

Condo
Bedrooms 3
2 Bathrooms

In the heart of Old Town and convenient to just about everything, this condo is set above a quaint brick and tree-lined courtyard that includes shops and restaurants. This three bedroom, two bath unit is in one of the only "stand-alone" buildings in the Duval Square complex.

Map View

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