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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 6 - 10 of 15 results matching your search criteria
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Ultimate Pool Cottage

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

This three-bedroom, three-full-bath cottage exudes the kind of at-ease ambiance that tells you you're right where you need to be to have the best vacation ever. The cottage is in the Meadows neighborhood on the grounds of an impressive Key West estate. Like something out of...

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...

La Hacienda

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

MAY STILL OPEN!

Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most distinctive two bedroom/two bath homes. Located on fashionable Southard Street in the heart of Old Town, the first thing you notice as...

Bahamian Rhapsody

Monthly and Seasonal Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

This impeccably renovated property makes the perfect vacation getaway. At first glance, you can confirm its aesthetic appeal and secluded location half a block from Key West's celebrated Duval Street. If two bedrooms, two-and-a-half baths, an outstanding pool and deck area, and dedicated parking meet your...

Azure Hideaway

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

So you've decided to become one of those lucky enough to be vacationing in extraordinary Key West this year! Your next step is to choose just the right residence. With two plus bedrooms, two full baths, and a stellar location, Azure Hideaway could easily be your...

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