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50 properties available
While Old Town Key West has its fair share of impressive homes, few can compare to ENVY OF THE ISLAND, a freshly built two-story private home that combines the appearance and charm of a historic Keys home with all of the modern conveniences you have come to appreciate in new construction. This head-turning property boasts five bedrooms - unheard of
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
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
This ultimate Key West dream home is nestled in the highly desirable residential Old Town neighborhood of Solares Hill, just a quick walk from Duval Street and the Historic Seaport areas. No expense has been spared in upgrading and furnishing VILLA OLIVIETTA; the most up-to-date appliances and technology can be found in each room. The comfortable a
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
For many, the artistic island culture of Key West is an intricate piece of its magic. THE ARTISTS' MUSE is an ode to that notion. This home, with its rich history of artists living in residence or visiting as guests, has been recently redesigned to celebrate art, culture, and the upscale island life. A spacious main living and dining area, a brand
THE POLYNESIAN HOUSE is an extraordinarily unique and whimsical home, designed to capture the culture and experience of island life in an upscale private home. Viewing this home from the street, you'll know immediately how the name THE POLYNESIAN HOUSE came to be; The Polynesian-style curved roofs of the two rooms sitting atop this home are the fir
Imagine a traditional conch home in the Solares Hill section of Old Town. MAISON TROPICALE is stunningly restored then decorated in a post-modern style with vivid colors and sophisticated decor. Every room is adorned with colorful art and has been furnished with unique show pieces. This brilliant decor is set against a backdrop of original Dade Cou
MODERN IN THE MEADOWS proves you can blend modern and tropical styles into a beautifully laidback yet chic home. This fabulous monthly rental shines with its high-end upgrades, refined decor and upscale accommodations. Located in the quiet, sought-after Meadows neighborhood you’ll be treated to a month of relaxation in a newly renovated home that f
Located in Truman Annex, a gated community with some of the most impressive homes in Key West, this exceptional home stands out from all the rest. NOONA'S MANSION is nestled in a quiet cul-de-sac facing the ocean on a beautifully landscaped piece of property. This impressive home features six spacious bedrooms, a fully equipped kitchen, a stunning
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
Traveling with a large group requires a special home. To maximize comfort, large common areas are offered both indoor and outdoor. Private bedroom accommodations with en-suite bathrooms and TVs are a must. And don't forget about the location! This home is easily accessible to the favorites of Old Town for when the group (finally) reaches a decision
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