4-5 Bedroom Monthly Rentals
18 properties available
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
SOUTHERN STAR is a modern Key West home nestled in the quiet Meadows neighborhood of Old Town that combines the island way and the sweet life of the South. With wide porches, a breezy interior, cathedral ceilings, and an apparent southern charm, it's easy to see where this home gets its name. In addition to its distinct southern features, this home
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
SPIRIT OF KEY WEST was originally built in 1893 and features that authentic Key West charm found in other historic properties such as Hemingway’s House, Asa Tift’s manor and Truman’s Little White House. The vaulted ceilings and Dade County Pine walls harken back to a time when the cigar industry was booming and Key West featured more millionaires p
SOUTHERNMOST BLISS is a historic Key West eyebrow home that recently underwent a complete renovation, and the result is nothing short of pure bliss. This home was designed to combine the best of classic Key West with luxurious modern comfort. SOUTHERNMOST BLISS features 3 bedrooms in the main house and a 4th bedroom in the Guest House, each with it
Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather
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
Like many highlights of Key West, THE ADMIRAL'S ESTATE celebrates a rich history of the island while embracing a modern restoration. THE ADMIRAL'S ESTATE is a true historic Key West home, originally built for a high-ranking Naval Officer in the early 1900s. This impressive estate is armed with two living areas, a top-of-the-line gourmet kitchen, cl
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
Spanning an exclusive corner lot in the desirable Midtown neighborhood of Key West is a stunning compound-style home designed as the ultimate vacation destination for a family or group of friends seeking privacy and quiet only a short bike ride or walk from the bustling downtown Old Town area of Key West. In addition to four spacious bedrooms, this
Travelers from around the world would agree spending a month in Key West is truly a magical experience, especially when you find two classic conch homes made into one. This cozy compound perfectly captures the magic of the island, with its beautiful Dade County Pine walls, tropical decor, and the plunge pool waiting just outside. MARGARET’S MAGIC
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
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