Nightly & Weekly 4-5 Bedrooms
19 properties available
With a sense of gracious royalty, QUEEN OF LOUISA will treat you to an unforgettable stay in Key West. Her ideal location, modern interior, private pool and thoughtful touches throughout will ensure you and your group have everything you could want in a vacation rental. QUEEN OF LOUISA offers cozy bedrooms, a fully stocked kitchen and a fantastic o
If you’ve recently heard the Siren’s call beckoning you to Key West, it might be because you were drawn by the SIREN’S SERENADE luxurious interior, lush private backyard, and dream-like location. The moment you enter the gate, you’ll meet the Siren posed in her tropical garden. You’ll come around the lavish and very private pool area to enter this
Seals & Crofts said it best: ‘Diamond Girl, you sure do shine.’ Formerly known as Seventh Heaven, DIAMOND GIRL is a stunning two-story private home that epitomizes island living, with its’ distinct exterior eyebrow design, ample indoor and outdoor living space, and comfortable accommodations. Once here you’ll quickly realize this peaceful oasis
For a truly over-the-top Key West stay with your entire group, whether that be the whole family or your closest friends, STAR OF THE SEAPORT has the location, amenities, layout, and extra guest service to help host the island trip you envision. STAR OF THE SEAPORT is a luxurious private estate that occupies an expansive space on an iconic street in
The vacation opportunity of a lifetime awaits at GRAND KEY OASIS. This breathtaking one-of-a-kind property is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion that overlooks the exceptional backyard and resort-style private pool. The interior design of this compound will leave you marveling at the
For the ultimate stay in America's Paradise, what could be more perfect for your whole group than AMERICANA TROPICALE? This festive and patriotic home will promise a one-of-a-kind island experience. AMERICANA TROPICALE has 4 spacious bedrooms each complete with its own en-suite bathroom for privacy, a private saltwater pool, a fully equipped kitch
CASA VICTORIA, located in the heart of Old Town just two blocks from Duval Street, is a large 5 bedroom home built with the charm and quirkiness of early 20th century Key West. Dating back to the Cigar Manufacturers' era, CASA VICTORIA exudes the classic Old Town style that makes Key West such a unique vacation experience. This authentic Conch Hous
If your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, y
Tranquility. Peace. Relaxation. You’ll find these traits are in abundance at GARDEN OF EMMA. The open and airy interior of this exquisite Key West home will keep your group connected and present, while being the perfect complement to the tranquil, tropical exterior. The spacious backyard is your very own private oasis, complete with a lagoon-style
Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished estate occupies an entire block, making it the largest single property in the Annex. Formerly referred to as "Plantation Tropicale," with three dwellings, two kitchens (one indoor, one outdoor), a very large pool and enoug
SOUTHERNMOST HOSPITALITY V is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the form
Resembling a French Plantation, PLANTATION TROPICALE is an impressive island estate that occupies an entire corner block of the desirable Casa East neighborhood of Key West. This expansive property features nearly 3,000 square feet of indoor living space, a separate Guest House, beautifully maintained gardens, and a large private pool and cabana –
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