Featured Stays: History on Your Doorstep
To walk this history is to stay in the heart of Old Town — and two of our homes put you right in it.
Villa Josine (4BR/4.5BA, sleeps 8) — a beautifully restored example of a Key West “eyebrow house,” an 1800s style built to keep the upstairs cool long before air conditioning. Fully renovated with designer finishes, it offers four ensuite bedrooms, a quartz-and-Dade-County-pine kitchen, and a private pool framed by a wall of glass doors. Best of all for this story, it sits on Elizabeth Street just a few steps from the historic Key West Cemetery and two blocks from Duval. (Not pet-friendly.) Ideal for: Extended families or groups of up to eight who want a private pool and a true historic home, steps from the cemetery memorial and Duval Street.
Reel Paradise (3BR/2.5BA, sleeps 5) — a private townhouse tucked inside a small gated community in the Historic District, with a shared pool and tropical gardens, a Trex-covered front porch made for afternoon cocktails, a full kitchen, and on-site parking. It is a calm, secure home base for a family or small group exploring the island’s history on foot or by bike. Ideal for: A family or small group seeking a quiet, gated retreat with a shared pool, an easy walk or ride from Old Town’s landmarks.