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Old Town Key West Rentals

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Hilltop Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 4
Max Occupancy 4

Hilltop Hideaway is near the top of Solares Hill, the highest point in Key West, a mere 15 feet above sea level. ("Hilltop" is a word the locals use loosely in Key West!) This meticulously cared for two-bedroom, one full bath condo is near the center...

Blackbeard's Treasure

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

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 seafaring history, is a major understatement. The 1950's era art deco Steamplant...

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...

Serenity Now

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

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 an unforgettable Key West experience. The residence-aptly dubbed "Serenity Now"-provides privacy, contemporary...

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

MARCH STILL AVAILABLE!

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...

Island Time

Monthly and Seasonal Rentals
4 Bedrooms
2 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

Everyone and everything in Key West goes at its own speed, a wonderfully decelerated, human-friendly pace. Locals call it "island time." It's no accident that this beautifully restored 19th century home with four bedrooms and two full baths is named "Island Time" in honor of that...

The Sanctuary

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

END OF SEASON 2019 Still Open! Can be rented as a 3BR (for reduced rate) or 5 Bedroom - See Below!

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...

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