Monthly Rentals
45 properties available
Upscale island living is epitomized with this beautiful home, CAYO CALYPSO. This modern home is well appointed, spacious and comfortable. CAYO CALYPSO offers a relaxing tropical theme and prime location near the Beach. Enjoy easy walks to Higgs Beach and pier, community playgrounds, Salute Ristorante or Smathers Beach. Comfortable accommodations in
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)
Cayo Calypso
Private Home
3
bedrooms
3
baths
8
guests
4.9
(29)
The moment you arrive at this midtown mansion, you’ll know your time in Key West is going to be special. The circular driveway and covered portico provide a grand entrance, which set the stage for what awaits you inside. At over 3,900 square feet, ISLAND OPULENCE is one of the largest private residences in Key West. This impressive ranch-style home
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 Opulence
Private Home
4
bedrooms
4
baths
1
half-baths
11
guests
In the Historic Seaport area of Old Town, there is a house that will behold your eye. At first glance you'll see that HEAVENLY ZEN is beautifully maintained with carefully tended landscaping; however, nothing will prepare you for what is inside. As you walk in, you will feel an immediate sense of peace and relaxation. All of the spaces in this meti
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)
Heavenly Zen
Private Home
4
bedrooms
3
baths
8
guests
5
(46)
You have many choices when choosing where to stay in Key West, but the most unique way to get an authentic Key West experience is by spending your vacation in a classic conch cottage smack dab in the heart of Old Town. You know what they say - “In a world full of apples, be a pineapple.” Whether you’re on a writer’s retreat or simply need an escap
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 Poetic Pineapple
Private Home
2
bedrooms
2
baths
4
guests
5
(6)
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
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
3
bedrooms
2
baths
10
guests
5
(5)
CASA AVILA combines a rich history with a desirable Old Town location. Located two blocks from both the waterfront and Duval Street, this beautiful home is considered one of Old Town's original Grande Dames and proudly displays a historical preservation star. CASA AVILA was Key West's first prominent art gallery and one of the original homes in Old
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)
Casa Avila
Private Home
3
bedrooms
3
baths
8
guests
5
(2)
Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen large enough for a whole team of chefs to prepare dinner, CASA OLIVIANA has it all.THE LIVING AREA...The aforementioned living room is truly big enough for the whole family. The only d
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)
Casa Oliviana
Private Home
6
bedrooms
5
baths
12
guests
5
(33)
According to the classic song, the best remedy for a belly ache is to "put de lime in de coconut and drink 'em bot' up." Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME & THE COCONUT and let us handle de rest! THE LIME & THE COCONUT is a compound of t
The Lime & The Coconut
Compound
6
bedrooms
6
baths
2
half-baths
16
guests
4.9
(87)
If you’re looking for a Florida Keys home that rivals the seaside homes found in ‘Coastal Living’ magazine, look no further! COASTAL LOVING is an inviting two-story private home that offers a relaxing vacation setting and comfortable accommodations. This easy living home combines a classic Key West design with the finest modern updates and convenie
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)
Coastal Loving
Private Home
4
bedrooms
3
baths
8
guests
5
(8)
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
3
bedrooms
3
baths
1
half-baths
8
guests
5
(5)
A home designed to impress the most discerning travelers, LAYOVER IN PARADISE is an oasis of comfort sure to meet the expectations of those accustomed to first class treatment. LAYOVER IN PARADISE is a newly constructed private home in the Casa Marina neighborhood that offers three spacious private suites, each with a large en-suite bathroom - and
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)
Layover In Paradise
Private Home
3
bedrooms
3
baths
8
guests
5
(7)
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
3
bedrooms
3
baths
1
half-baths
10
guests
5
(11)
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