Key West 3 Bedroom Monthly Home & Condo Rentals
18 properties available
SUNSET POINT has everything you could want in a vacation home: it is close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET POINT with a very large balcony overlooking the Florida Bay and the Gulf of Mexico beyond.THE PRIVATE GATED COMMUNITY...Sunset Marina is a gated communit
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Sunset Point
Condo
$175.00 - $487.00 / per night
3
bedrooms
2
baths
6
guests
5
(23)
You don’t often find new construction in Old Town, the historic district of Key West known for classic conch homes and walkable streets, but recently a spectacular new home was built smack dab in the middle of it all. CASITA OLIVIETTA is a newly built breathtaking home that allows you to enjoy the luxury of brand-new construction in the prime locat
Casita Olivietta
Private Home
$215.00 - $775.00 / per night
3
bedrooms
4
baths
1
half-baths
8
guests
From the moment you arrive to this spectacular Florida Keys home, you will feel all your stresses and worries simply melt away. CAREFREE ON CUDJOE is an expansive waterfront property that evokes the easy-going nature of Keys living and provides an ideal setting for those looking to enjoy a ‘carefree’ vacation. There will certainly not be a shortage
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Carefree on Cudjoe
Private Home
$265.00 - $908.00 / per night
3
bedrooms
3
baths
9
guests
5
(3)
MODERN MAJESTY is a stunning, freshly renovated three-bedroom condo that checks every box for the perfect vacation rental. This large unit is laid out over one floor, meaning you don’t have to worry about stairs. The three bedrooms are luxuriously appointed suites, each with their own en-suite bathroom. The kitchen is as functional as it is beautif
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Modern Majesty
Condo
$325.00 - $935.00 / per night
3
bedrooms
3
baths
1
half-baths
6
guests
5
(4)
THE GILDED PINEAPPLE is a classic Key West home located on one of the most desirable streets in Old Town. This completely renovated, historic home gets its’ name from the elegant, oversized golden door knocker shaped like a pineapple that graces the front door – one of the many subtle touches that adds to the charm. THE GILDED PINEAPPLE features a
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
The Gilded Pineapple
Private Home
$400.00 - $1,110.00 / per night
3
bedrooms
3
baths
6
guests
It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Vil
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Seaport Sensation
Townhome
$275.00 - $865.00 / per night
3
bedrooms
3
baths
1
half-baths
8
guests
5
(1)
In the same way that the island of Key West has captured the hearts of so many, this charming monthly vacation home will capture yours. ISLAND INSPIRATION combines the appearance and charm of a historic Keys home, with all of the modern conveniences you have come to appreciate. This special home is situated on Margaret Street at the edge of where O
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Island Inspiration
Private Home
$275.00 - $913.00 / per night
3
bedrooms
3
baths
1
half-baths
10
guests
5
(11)
Like the mystical flower this home is named after, THE ENCHANTED ROSE is a breathtaking monthly vacation home that stands out from the rest. Situated on Rose Street, in the Beachside district of Key West, just a couple blocks from Smathers Beach, this recently renovated one-story home provides a magical setting for vacationers looking to experience
HOT
29
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
The Enchanted Rose
Private Home
$225.00 - $773.00 / per night
3
bedrooms
2
baths
10
guests
5
(4)
Located on Solares Hill in the heart of Old Town, HAVANA HOUSE captures the simple elegance of Key West's Conch homes of the fifties, when it was still possible to sail to Havana.THE LIVING AREA...The living room of HAVANA HOUSE has a vaulted ceiling, with walls of Dade County Pine. There is a large flat screen TV and comfortable seating for everyo
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Havana House
Private Home
$225.00 - $815.00 / per night
3
bedrooms
2
baths
8
guests
5
(51)
SUNSET DREAMS has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET DREAMS with a large balcony overlooking Florida Bay and the Gulf of Mexico beyond.THE PRIVATE GATED COMMUNITY...Sunset Marina is a gated community
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Sunset Dreams
Condo
$175.00 - $487.00 / per night
3
bedrooms
2
baths
8
guests
5
(12)
SUNDRENCHED REFLECTIONS is very close to Old Town, with access to all the attractions that Key West has to offer. Yet, you'll be in your own world with a large sundrenched balcony overlooking Florida Bay and the Gulf of Mexico beyond. THE PRIVATE GATED COMMUNITY... Sunset Marina is a gated community located on Stock Island, right off the entrance t
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Sundrenched Reflections
Condo
$175.00 - $487.00 / per night
3
bedrooms
2
baths
6
guests
5
(10)
ISLAND BLISS is a classic Old Town Key West home, complete with delicate gingerbread accents, a classic Southern front porch with rocking chairs, and lush, tropical foliage tastefully surrounding the property. This beautiful, historic two-story home has been lovingly cared for and restored with a mix of modern touches and traditional Key West influ
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Island Bliss
Private Home
$250.00 - $720.00 / per night
3
bedrooms
2
baths
8
guests
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