You are here

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

Vista Fresco

Condo
Bedrooms 2
2 Bathrooms

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst friendly neighbors. The 1800 Atlantic complex sits on 400 feet of oceanfront property.

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. 

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.

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

Colony Poolside

House
One Bedroom
One Bathroom

Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork.

Villa Serena @ Duval Square

Condo
Bedrooms 2
2.5 Bathrooms

Open the door to Villa Serena and find yourself transported to a peaceful sanctuary.  Recently renovated in February 2018, Villa Serena is the perfect space for your relaxing vacation.

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.

Southard Horse Conch Suite - L

House
One Bedroom
One Bathroom

The Horse Conch is a one bedroom one bathroom suite in a house consisting of three vacation suites. Decorated with tropical color palette and has a queen bed. Accessed from the second floor covered porch that overlooks the shared gardens and pool below.

Canalfront Cottage

House
Bedrooms 2
One Bathroom

28 Day Minimum Rental

Open water access!

Away from the hustle and bustle of Old Town–  behind the coral topped privacy fence– lies this stunning, secluded pied-a-terre overlooking the Riviera canal.

Map View