Above: View from Latitudes restaurant at Sunset Key Cottages, Key West, Florida

Key West Hotels: A Hit and Two Misses

Improbably, Key West was the richest city (per capita) in the United States in the mid-1800s. Locals would salvage the cargoes of ships wrecked on the shallow reefs surrounding much of the island. The most successful salvagers built grand mansions, many of which still stand to this day. Indeed, much of the city’s old center appears as it did a century ago. These neighborhoods are sharply contrasted by the raucous atmosphere of upper Duval Street, reminiscent of Bourbon Street in New Orleans, lined by souvenir shops, kitschy “art galleries” and margarita-fueled watering holes.

But Key West has at least as much to offer in terms of literature and history as it does alcohol and revelry. Ernest Hemingway famously lived there, working on novels such as “A Farewell to Arms” and “To Have and Have Not.” Other major literary figures associated with Key West include Tennessee Williams and Wallace Stevens. Shel Silverstein bought a house on William Street in the 1980s, and Meg Cabot still has a home on the island, as does Judy Blume, who (in nonpandemic times) can often be found in her delightful bookshop, Books & Books. Key West is also home to the Little White House, where Harry Truman spent some 175 days of his presidency, debating major postwar policies such as the Truman Doctrine and the Marshall Plan. (And I always make a pilgrimage to the little white house that served as the original office of Pan American World Airways. The airline ran the country’s first international commercial flights, connecting Key West and Havana. A microbrewery and restaurant now occupy the building.)

Sunset Key Cottages

Main beach at Sunset Key Cottages, Key West, Florida - Photo by Andrew Harper editor

Aside from the inn we currently recommend, The Gardens Hotel, the property in Key West about which I receive the most inquiries is Sunset Key Cottages. This 40-room resort went through phases as a Hilton, a Westin and a Luxury Collection member, and it is now independently owned. I had hoped that its location on 27-acre Sunset Key, an artificial island accessible only via a short ferry ride from Key West, would give the property the feel of a hideaway, removed from the bustle but easy to reach from downtown. Certainly its price indicates that Sunset Key Cottages regards itself as a luxury resort of the highest order.

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Above: View from Latitudes restaurant at Sunset Key Cottages, Key West, Florida

Read More from Our Trip:

Three-Hour Tours: Boating in the Keys Marathon’s Marvelous Turtle Hospital Key West Walking Tours Contrasting Resorts in the Florida Keys Favorite Florida Keys Restaurants