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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

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. 

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.

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.

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.

Dreaming on Duval III

House
Bedrooms 3
3.5 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!

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.

Newton Street Hideaway

House
One Bedroom
2 Bathrooms

28 Day Minimum Rental:  Newton Street Hideaway is located in The Meadows of Key West, a lovely, quiet and historic neighborhood known for it's tranquil tree-lined streets and classic architecture.

Thompson's Court

House
Bedrooms 3
2 Bathrooms

28 Day Minimum rental:  Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-style design with large doors and windows that let in the natural sunshine.  The large living area is decorated in charming vintage wallpaper and bright, tropical colors.

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. 

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.

Map View