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Old Town Key West Rentals

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la Palm d'or

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

SPECIAL FALL prices for open time periods between now and year end!

The name of this home-Palm d'or-echoes the Palme d'Or, the highest award at the Cannes Film Festival. In this case, the award goes to the palm tree landscaping of this two-bedroom, two full-bath residence....

Blackbeard's Treasure

Monthly and Seasonal Rentals
3 Bedrooms
3.5 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

SPECIAL FALL prices for open time periods between now and year end!

In addition, save 3% off final negotiated rates if you pay by check.

To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in...

Serenity Now

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

SPECIAL FALL prices for open time periods between now and year end!

Vacation connoisseurs agree that the most important element of a truly memorable trip is the housing you choose. This three-bedroom, two-full-bath home in the heart of Old Town makes the perfect first decision for...

Anchor's Away

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom, two-full-bath conch cottage in Old Town Key West. Recently restored and updated to include amenities such as a heated pool with rainforest waterfall, granite counter tops,...

Amelia Lane

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

Sun, fun, and relaxation are the mainstays of life on the little island of Key West. To enjoy this tropical haven for yourself, the first step is securing the right accommodations. If a single-family home with three bedrooms, two full baths, a sparkling private pool, two...

Amelia by the Sea

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

SPECIAL FALL prices for open time periods between now and year end!

This superbly designed three-bedroom, two-bath conch house named "Amelia By the Sea" is located, as the name suggests, near sandy beaches and the wildly beautiful Atlantic Ocean. It's part of Bahama Village, a 16-block...

Maximo Cabana

Monthly and Seasonal Rentals
3 Bedrooms
3 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

Looking for an ideal vacation? This charming three-bedroom, three-bath home is the perfect getaway spot. The style? A classic Key West eyebrow with two saw-tooth additions and plenty of Dade County pine. The story? The name "Maximo Cabana" commemorates Maximo Diaz, who bought the house in...

Hemingway's Library

Monthly and Seasonal Rentals
3 Bedrooms
2.5 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and proximity...

The Sanctuary

Monthly and Seasonal Rentals
5 Bedrooms
5 Bathrooms
Comfortably Sleeps 10
Max Occupancy 10

SPECIAL FALL prices for open time periods between now and year end!

Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in...

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