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Key West Vacation Rentals

Book Key West’s Best Vacation Rentals

Rent Key West 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

La Brisa #403E Ocean Vista

Condo
Bedrooms 2
2 Bathrooms

La Brisa Beach Condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation.

Southard Street - Queen Conch

House
Bedrooms 4
4 Bathrooms

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.

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.

Colony Poolside

House
One Bedroom
One Bathroom
Colony Poolside is a charming one bedroom bungalow located near the Historic Key West cemetery. This one level cottage has an open living/dining area, full kitchen and spacious bedroom with king size bed. Located on a compound with a large shared pool.

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. 

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.

Whitehead House

House
Bedrooms 3
2 Bathrooms

Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West.

Map View

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