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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

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!

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.

Townhomes on Windsor #6

House
Bedrooms 3
3.5 Bathrooms

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft.

Beach Club #304

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 as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom condo.

Cayo Hueso Cottage

House
Bedrooms 2
3 Bathrooms

28 DAY MINIMUM RENTAL

Cayo Hueso Cottage is found on a quiet street in the Heart of Old Town. Set amid plumerias and palm trees, the property is conveniently located near favorite restaurants like Mangia Mangia, Michael's, Azur, 5 Brothers and Date & Thyme.

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.

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. 

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.

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

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