The Best Hotels in Key West Historic District
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
- 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
- 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
- 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
- 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?
- Explore our entire list of the best hotels in Key West.
- Browse through our collection of the best hotels in Key West on the beach or the best hotels in Key West for couples.
- Expand your search to include the best hotels in the Florida Keys.
- Check out all the best places to stay in Florida.
- Alternatively, contact one of our friendly Gurus for advice.
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Winslow's Bungalows Key West 85 rooms from $300
Local exploring - Key West offers frequent festivals to tropical open-air bars, the sliver of an island balances revelry and relaxationGroups - The largest of the Kimpton group on Key West with three pools and spacious rooms and suitesSwimming Pool - Three outdoor poolsSailing - Can be booked nearby.
Check AvailabilityThe largest of the 5 Kimpton hotels on Key West. Chic spacious rooms with artful, bohemian interiors and elegant touches such as summer cane beds and private patios with lush furnishings. The idyllic space has three private pools, an outdoor bar and vibrant gardens. Suitable for groups or couples. See More
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The Mermaid and The Alligator Key West 9 rooms from $268
Romantic Break - Plan a special weekend away with a bottle of Veuve Cliquot Champagne and chocolate-dipped strawberries on arrivalLocal exploring - The shops, galleries, and restaurants of Duval Street are just three streets awayBeach Life - With bicycles to rent, spend an entire day exploring the beaches of Key WestAdult Only
Check AvailabilityAn elegant and intimate B&B in Key West. Rooms are spacious and stylish with tropical decor, four-poster beds, angled bay windows and luxury linens. Enjoy a homemade breakfast on the lush and tropical terrace. On hot days, relax by the pool or grab a bicycle and explore the beaches of Key West. See More
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The Conch House Heritage Inn Key West 10 rooms from $268
Local exploring - The B&B is minutes away from the Key West Historic Seaport, best sightseeing, beaches, water sports and restaurantsFishing - Spend a day on a charter deep sea fishing boatAdult OnlySeaside - Ideal for a seaside holiday.
Check AvailabilityA tropical and elegant inn situated in Old Town Florida Keys. Rooms are classical and coastal with ceiling fans, traditional antique furnishings, artworks and large bathrooms with walk-in showers. Enjoy a delicious breakfast poolside with fresh-squeezed juices and champagne mimosas. A perfect stay. See More
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The Paradise Inn Key West 18 rooms from $319
Diving - It is possible to go scuba diving in the waters surrounding the island.Sailing - Go for a sunset sail on the ocean.Restrictions on children - No children under the age of 18Swimming Pool - Outdoor pool
Check AvailabilityA tranquil adults-only bed and breakfast with outdoor hot tub and fountain fed pool. The exquisitely simple rooms, painted in calming whites and nudes, are flooded with natural light and furnished with an eye for Floridian refinement. Breakfast and wine and cheese happy hour are included. See More
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Ella's Cottages - Key West Historic Inns Key West 22 rooms from $300
Local exploring - The hotel is the perfect base for discovering Key West's rich culture and its beautiful beachesTotal relaxation - Soak up the Florida sun and lounge by the pool with a good bookDiving - Good diving nearby.Kayaking - Available locally.
Check AvailabilityA luxurious and intimate guesthouse set amongst a lush tropical garden. Charming guestrooms and cottages feature soft hues dotted with bright accents, in-room yoga mats, private patios and large rainfall showers. Sunbathe by the pool cloistered by banana palms or roam Key West by bike. Idyllic! See More
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Written by Katie Harris
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