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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

Villa de Palmas

House
Bedrooms 3
3 Bathrooms

28 Day minimum Rental: Tucked away behind a contemporary privacy fence and an attractive cobblestoned driveway is this hidden jewel of a home in mid-town Key West. 

Packer Retreat

House
Bedrooms 3
3.5 Bathrooms

28 Day Minimum rental:  Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district.

La Brisa #303W

Condo
Bedrooms 2
2 Bathrooms

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

Coconut Cabana

House
Bedrooms 3
2 Bathrooms

A quintessential "Old Town Key West" home, located in the Historic District and just one half a block off Duval Street.

Artist's House @ Duval Square

Condo
Bedrooms 2
2.5 Bathrooms

This 2 bedroom, 2.5 bath rooftop town home is located within the quaint community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located right in the heart of old town Key West.

Reynold's Retreat

House
Bedrooms 3
3 Bathrooms

28 Day Minimum rental:  Reynolds Retreat is quintessential Key West living.  Located just a few blocks off Duval Street, Reynolds Retreat is a delightful cottage filled with historic charm and modern convenience.

Duval Square Retreat

Condo
Bedrooms 2
2.5 Bathrooms

Located in the heart of Old Town, Duval Square is a charming brick-paved and tree-lined courtyard complex located at the quieter end of Duval Street. The residential units are located upstairs, while quaint shops and restaurants occupy the courtyard below.

Colony Calypso

House
One Bedroom
One Bathroom

Located in The Colony, a secluded compound just steps from Duval Street, Colony Calypso is a peaceful retreat. Enter the home through the tranquil and inviting living space, accented with sage green walls, new tile floors and pops of color from local artwork and photography.

Escape on Fleming

House
Bedrooms 2
One Bathroom

28 Day Minimum Rental:  This comfortable and fresh two bedroom, one bathroom apartment is located in the heart of Old Town Key West.

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.

Map View