Resort: Casa Marina Key West, Curio Collection by Hilton
After an $80 million top-to-bottom renovation, Casa Marina has reclaimed its place as Key West’s most glamorous resort. Long celebrated as the island’s grande dame, the circa-1920 landmark now feels like the ultimate Florida daydream brought into the present—airy, elegant, and unmistakably Key West.
The soaring lobby sets the tone with restored wooden beams, arched windows, and green-tinted furnishings that hint at the sea beyond. Step outside to 1,100 feet of private beach—the largest on the island—where loungers line the sand and two historic piers frame postcard sunsets.
The guest rooms balance heritage and new-age polish with rattan textures, woven fabrics, and open, sun-washed layouts. Days drift between the dual oceanfront pools, the serene Spa al Mare, and beachfront dining at Dorada Key West, where Baja-Med flavors meet local catch. The Canary Room turns cocktail hour into theater, with island-painted walls and pours featuring a house-exclusive Papa’s Pilar Rum.
Just far enough from Duval Street to feel secluded yet central to the island’s spirit, Casa Marina is where Old Key West sophistication and modern luxury meet—an icon reborn for the next century of sunseekers. —Paul Rubio
Inn: Key West Historic Inns
For travelers drawn to the island’s authentic charm, Key West Historic Inns offers five beautifully preserved properties that keep the past alive without sacrificing comfort. Each inn occupies a distinctive corner of Old Town, tucked along quiet residential streets yet within walking distance of Duval Street and the Historic Seaport. Shady gardens, wraparound porches, and vintage architectural details remind guests that this is the Key West of another time, carefully refreshed for today’s traveler.
The largest of the group, Winslow’s Bungalows, comprises several whitewashed cottages and homes dating back to 1856. Tropical landscaping, hammocks, and hidden pools create a sense of discovery at every turn. Interiors marry retro-chic accents with island ease, while the daily continental breakfast adds to the homey rhythm of the stay.
On Eaton Street, Fitch Lodge captures the essence of Old Key West in a cluster of restored conch houses. Its covert lobby and serene pool attract guests who prefer a neighborhood feel. Among its most coveted rooms is the 800-square-foot Seaquarters, featuring two bedrooms, a kitchen, and a generous living area. Together, these historic inns are a testament to the enduring soul of Key West: storied, welcoming, and unabashedly unique. —P.R.
Rental: Lunara Bay
Key West is known more for its relaxed attitude than its focus on bespoke luxury, but Lunara Bay is here to change that. The waterfront enclave of 26 four-to-eight-bedroom residences, some of which have direct water views, feels more like a private gated community than a vacation rental.
The homes are grand in scale, with lots of public areas for gathering. Indoors, expect cool coastal palettes, furniture you can sink into, and entertainment-ready kitchens. Sliding glass doors open to an outdoor dining patio overlooking a fenced area with a swimming pool, summer kitchen, grill, fire pit, and lots of seating to accommodate a crowd. Indeed, the best way to experience Lunara Bay is with friends and family, so bring your entire crew.
Guest Experience Managers (GEMs) are on hand to stock the fridge and plan fishing trips or
sunset sails. Come dinnertime, they can make restaurant reservations (yes, even the tough ones) or hire a private chef to whip up some fresh Florida lobster or whatever your heart desires. The idea is to make everything seamless so you can sit back and chill out—maybe with the archetypal margarita in hand. —Daphne Nikolopoulos
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