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Five boutique hotels.
Five distinct personalities.
One unforgettable Key West.
Key West Historic Inns
Key West has always belonged to those who see life a little differently. Across five hotels, Key West Historic Inns captures that same independent character with places that feel connected to the island rather than simply set within it. Here, historic streets lead home, afternoons find their way to the pool, and the best parts of Key West are never far from the front door. This is a collection shaped by the island itself, made for those who want to know Key West beyond the postcard.
Lively. Social. Effortless Connection.
Three pools, a lively bar, live music, and plenty of room to gather make Winslow’s Bungalows the social side of Key West Historic Inns. Just a block from Duval Street and within walking distance of the island’s restaurants, shops, and nightlife, it’s made for days by the pool that turn into nights out on the town. Colorful, energetic, and always up for a good time, Winslow’s is where Key West comes to life.
Authentic. Comfortable. Timeless.
For travelers who prefer the feeling of a Key West home, Ridley House offers a more residential way to stay. Set in Old Town near the Historic Seaport, this historic estate pairs the character of a private residence with warm, personal hospitality. Comfortable, gracious, and rich with history, Ridley House feels like a place you belong from the moment you arrive.
Private. Unexpected. Unmistakably Key West.
Steps from the Key West Lighthouse and the Ernest Hemingway Home & Museum, Lighthouse Hotel sits at the intersection of some of the island’s most colorful stories. Its connection to Hemingway, Isabel, and a long legacy of welcoming guests gives the hotel a personality all its own. Intimate, storied, and a little unexpected, it’s a stay that could only happen in Key West.
Intimate. Elevated. Romantic.
Made for couples, Ella’s Cottages brings a more romantic side of Key West to life. Set in the heart of Old Town, just a short walk from Duval Street, the cottages pair an intimate setting with the freedom to step out and experience the island together. Full of character and inspired by a love story of its own, Ella’s is made for romantic getaways, long weekends, and time that belongs to just the two of you.
Charming. Walkable. Adventurous.
Fitch Lodge puts the adventurous side of Key West within easy reach. Just a short walk from the Historic Seaport, waterfront dining, and endless ways to get out on the water, it’s an effortless home base for exploring the island. Comfortable, welcoming, and connected to Key West’s maritime side, Fitch Lodge is made for days that start with a plan and often turn into something better.