The Top 8 Hotels Near Winslow's Bungalows
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A cluster of historically roofed houses in Key West's old quarter, threaded together by pools and contemporary interiors that don't overwhelm the bones underneath. The Bungalow Bar sits poolside in the kind of unhurried sprawl that makes you forget you came here for a room.
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The Marquesa sits in Old Town among the ghosts of Hemingway and Williams, a pocket of unhurried elegance that has somehow resisted the cruise-ship sprawl consuming the rest of the island. Narrow lanes, courtyard gardens, and the particular quiet of a place where history still matters more than novelty define the experience here.
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The Marker rises from two acres of waterfront as Key West's first new hotel in two decades, a luxury property that somehow earned local blessing by respecting sight lines to the Gulf. Its thoughtful design avoids the cranes and sprawl that typically accompany such development, settling instead into the island's rhythm.
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A rambling cluster of nineteenth-century buildings anchors this Key West property mere steps from the lighthouse and Hemingway's old house, its grounds organized around a banyan tree and pool. The rooms marry tropical prints with contemporary furnishings; Isabel's bar trades in Hemingway cocktails and morning bloody marys, a comfort as reliable as the humid air.
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Sandwiched between the turquoise Atlantic and Duval Street's carnival of bars and shops, this 1950s beachfront institution has traded its dated interiors for a cleaner midcentury-modern aesthetic—all white walls, cobalt trim, and garden views. The newly acquired Victorian guesthouses next door, reserved for adults, suggest the place is finally catching up to its own romantic geography.
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On Stock Island's working waterfront, The Perry Hotel arrives as a carefully composed counterpoint to Key West's tourist sprawl, its modernist lines and considered interiors suggesting something more ambitious than the island's usual offerings. The Marina anchors the place—boats and salt air as much a part of the experience as the rooms themselves.
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A private island accessible only by yacht—formerly a retreat of Harry Truman's—stages an escape from the Overseas Highway's ordinary sprawl into something closer to illusion. The meal here arrives as part of a larger bargain: solitude, salt air, and the knowledge that you've left the mainland behind.
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Midway between Key Largo and Key West, this twenty-four-acre resort offers the self-contained luxury of five pools and a private beach far from the bohemian clutter of the archipelago's southern tip. Nearly two hundred suites and a spa suggest the Keys reimagined as a retreat rather than a waystation.