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Key West's historic Old Town is located on the waterfront and is arguably the city's most picturesque district. The area is filled with grand mansions and charming cottages, some dating back to the 1800s. Nowadays the waterfront is a popular area with restaurants, bars, museums, and fishing and sailing charters. It also has a good selection of hotels ranging from grand luxury properties to charming guesthouses set in converted historic homes. Our hotel experts have scanned the area to bring you a collection of the best hotels in Key West Historic District chosen on their amenities, service, and design. Whether you want a romantic hideaway, a quaint B&B, or something a little more upmarket — there are options to suit most tastes. So why not browse through our collection to start planning your next trip?
For luxury
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- Winslow's Bungalows is the largest Kimpton hotel on Key West. Chic rooms have bohemian interiors with elegant touches such as summer cane beds and private patios. With three outdoor pools, an atmospheric bar, and verdant gardens — this is a luxurious choice.
For a B&B
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- The Mermaid and The Alligator is an elegant and intimate B&B. Rooms are spacious and stylish with tropical decor, four-poster beds, angled bay windows, and luxury linens. With quiet terraces, a large pool, and bicycles to take to the beach — pick this for a charming home-away-from-home.
- The Conch House Heritage Inn is a pretty clapboard inn with green shutters, quiet terraces, and a large pool. Classically styled rooms have antique furnishings, traditional artworks and pastel hues. Breakfasts are served poolside with freshly-squeezed juices and champagne mimosas. A luxurious B&B.
For a boutique
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- Ella's Cottages is an intimate boutique guesthouse set amongst a lush tropical garden. Stylish rooms and cottages have wooden floors, modern furniture and art, in-room yoga mats, private patios and large rainfall showers. With a gorgeous pool cloistered by banana palms, this is an idyllic stay.
For couples
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- The Paradise Inn is a tranquil bed and breakfast with an outdoor hot tub and fountain fed pool. Lovely rooms are painted in neutral hues and are flooded with natural light. With an adults-only policy and wine and cheese served in the evenings, this is a good option for couples.
Still not sure where to book?