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Monthly

Take a Long Vacation to Key West 

Rent Key West Vacations manages an amazing variety of Key West Monthly Rentals. Our townhomes, condos, and cottages are located in old town on Duval Square, near Key West’s famous attractions and nightlife. Many of our monthly rentals feature private pools and classic Key West architecture. 

Key West is the perfect place to relax, escape, and enjoy the Florida beach life. Upon arriving in Key West, you’ll immediately feel its energy. The longer you stay, the more you can enjoy.

Stay in Key West for Months!

Age 12 and under.

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Canalfront Cottage

House
Bedrooms 2
One Bathroom

28 Day Minimum Rental

Open water access!

Away from the hustle and bustle of Old Town–  behind the coral topped privacy fence– lies this stunning, secluded pied-a-terre overlooking the Riviera canal.

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Newton Street Hideaway

House
One Bedroom
2 Bathrooms

28 Day Minimum Rental:  Newton Street Hideaway is located in The Meadows of Key West, a lovely, quiet and historic neighborhood known for it's tranquil tree-lined streets and classic architecture.

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Albury Bungalow

House
Bedrooms 2
2 Bathrooms

28 Day Minimum Rental:  A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one bedroom, one bathroom house also boasts a separate cottage bedroom with its own bathroom.

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Angela Cottage

House
Bedrooms 2
2 Bathrooms

28 Day Minimum Rental:  This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a great central location to get to the Historic seaport or new town.

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Duval Square Delight

Condo
Bedrooms 2
2.5 Bathrooms

28 Day Minimum Rental:  Duval Square Delight is located in a quaint town home community just steps from Duval Street. Upstairs there are residential units and a rooftop pool, while downstairs there are shops and restaurants surrounded by cobblestones and mature, tropical landscaping.

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Escape on Fleming

House
Bedrooms 2
One Bathroom

28 Day Minimum Rental:  This comfortable and fresh two bedroom, one bathroom apartment is located in the heart of Old Town Key West.

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La Brisa #303W

Condo
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential condominium is situated opposite the largest beach on the island, while offering the amenities of a resort hotel.

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Sanctuary on Simonton

Condo
Bedrooms 2.5
3 Bathrooms

28 DAY MINIMUM- Dogs allowed, with restrictions

Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect extended-stay getaway.

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Southard Sophistication

House
Bedrooms 2
2 Bathrooms

28 Day Minimum rental:  This restoration of a majestic Key West bungalow is simply incredible. Modernists will love this property. This two bedroom, two bath home has just been completely renovated.

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