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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

Havana Lane

House
Bedrooms 2
2 Bathrooms

Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends.

Southard Rooster Conch Suite - R

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.

Bali Hideaway

Studio/Efficiency
Bedrooms 0.5
One Bathroom

Perfect for two, this Bali-style studio cottage has it all:  comfort, privacy and location.

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. 

Duval Square Penthouse

Condo
Bedrooms 4
4.5 Bathrooms

Freshly renovated in January 2019- and ready for you! 

Duval Square Penthouse has enough luxurious square footage for your whole crew to gather, relax, and make lasting memories together. 

Namaste

House
One Bedroom
2 Bathrooms

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds: relaxing and taking advantage of all that Key West has to offer.

Casa de Cuba

House
Bedrooms 3
2 Bathrooms

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat.

Duval Square Retreat

Condo
Bedrooms 2
2.5 Bathrooms

Located in the heart of Old Town, Duval Square is a charming brick-paved and tree-lined courtyard complex located at the quieter end of Duval Street. The residential units are located upstairs, while quaint shops and restaurants occupy the courtyard below.

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.

Map View

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