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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

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.

Pete's West Cottage

House
Bedrooms 2
One Bathroom

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. 

Southard Queen Conch Suite

House
Bedrooms 2
2 Bathrooms

Southard Street Downstairs Queen Conch is a two bedroom two bathroom retreat in a house consisting of three vacation suites. Open floor plan with French doors that open to the large shared sunny pool surrounded by beautiful landscaped garden.

Townhomes on Windsor #5

Villa
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.

Ann Street Cottage

House
One Bedroom
1.5 Bathrooms

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage, a charming one bedroom cottage.

Beach Club #408

Condo
Bedrooms 4
3 Bathrooms

Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths.

South St. Cottage

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  South Street Cottage is a bright and sunny "pool home" situated on a quiet street in the coveted and quiet Casa Marina district of Key West.

Southard Rooster Conch Suite

House
One Bedroom
One Bathroom
Rooster 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.

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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