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Key West Monthly Vacation Rentals

For an extended stay on Key West

Key West Monthly and Seasonal Rentals are the perfect option for an extended stay in Paradise. Historic Hideaways offers numerous options to make your stay hassle-free and filled with the best that Key West and the Florida Keys have to offer. Monthly/Seasonal Rentals have 30 day minimums. Except for Jan - March, they are not restricted to calendar months. So your arrival or departure date can be any day of the month, so long as your reservation is for at least 30 days.  Please keep this in mind when selecting your dates to be sure you meet the minimum stay rule in order to bring up available options. (Due to strict City regulations, no exceptions may be made to the minimum stay.) Discounts are often available for monthlies, especially in off-season or if staying for multiple months…so please ask! Monthly/Seasonal rentals have a cap on utilities such as electric, water, and propane. Please see our FAQ page for other rules & items specifically related to Monthly/Seasonal vacation rentals.

Displaying 1 - 5 of 19 results matching your search criteria
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Paradise Grand

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

Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-bath estate, is all about. The house and private grounds and off-street parking occupy a whole city block of historic Old Town, exceptional spaciousness on the small island of Key West. Copious...

The Sanctuary

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

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 hydro massage spa, graceful waterfall, and outdoor rain shower. Five doors of...

Amelia by the Sea

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

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 historic subsection of Old Town Key West that hosts some of the...

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,...

Hemingway's Library

Monthly and Seasonal Rentals
3 Bedrooms
2 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...

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