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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 11 - 15 of 15 results matching your search criteria
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Anne's Hideaway

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

MAY & JUNE STILL OPEN!

For luxurious vacation living, dining, sleeping, and playing, this historic Conch Home on fashionable Southard Street in the heart of Old Town hits the bullseye. It has been totally renovated, keeping its original cottage essence while adding contemporary design updates and...

La Buena Vida

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

MAY STILL OPEN!

Quintessentially Key West in terms of location and architecture, La Buena Vida won't disappoint as your next vacation rental. In fact, you'll be delighted. The location is Old Town's Bahama Village, an artsy and cultural quarter offering some of the best attractions and...

La Isla Vita

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

Here's how to craft a perfect vacation. First, buy tickets to fabulous Key West. Second, shop for flipflops and shorts. Third, reserve La Isla Vita for your stay! This two-story, two-bedroom, three-bath home offers what you'd expect and then some. The "then-some" starts with private off-street...

Solares

Monthly and Seasonal Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

The art of island living involves making efficient use of limited space. This charming first-floor, one-bedroom apartment does just that. It occupies the rear portion of an award-winning 1890s Victorian home on Solares Hill, the highest point of land in Key West. This quiet Old Town...

Campbell Cottage

Monthly and Seasonal Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

Campbell Cottage is the perfect place for living large in an intimate, comfortable one bedroom/one bath cottage. A locked privacy fence surrounds the lushly landscaped Campbell Court compound, which has an enticing Monaco pool at its center. You can step off your front porch onto the...

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