Best Hotels in Key West Historic District

Top Hotels in Key West Historic District

This guide to the best luxury, 5-star, and design-forward hotels in Key West Historic District is manually curated by our editorial team based on first-hand research, verified guest reviews, location analysis, and overall service quality. Each hotel is selected to meet high standards of comfort, authenticity, and guest experience.

Paradise Inn - Adult Exclusive
Hotels
Key West, FL, USA

Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles. A complimentary continental breakfast is served in the lobby. The suites at Paradise Inn - Adult Exclusive include a sitting area with cable TV. A microwave, refrigerator, and coffee facilities are furnished in each accommodations. Free WiFi is provided. Enjoy complimentary wine and cheese hour on site at Paradise Inn - Adult Exclusive. Additional amenities include an outdoor pool with a fountain feature and an outdoor hot tub. The hotel is happy to arrange sightseeing tours. Higgs Beach and the Key West Aquarium are 5 minutes' drive from Paradise Inn - Adult Exclusive. The Key West Museum-Art & History is a 15-minute walk away.

Guest Reviews:

- "Great place to stay. Clean, comfy, quiet but close to everything!" - "Good Times!" - "Will come back" - "Absolutely wonderful. Sad we were there for only one night." - "It was my birthday weekend and I had an amazing time.." - "Great hideaway near center of town" - "Great location." - "Great." - "Can't rate the property, but the office staff member and management were fantastic."

The Mermaid & The Alligator
Hotels
Key West, FL, USA

Featuring an outdoor swimming pool, a garden as well as a shared lounge, The Mermaid & The Alligator is located in the center of Key West, a 11-minute walk from South Beach. The property is close to several well-known attractions, one mile from Key West Aquarium, a 19-minute walk from Mallory Dock and 1.1 miles from Mallory Square. Offering free WiFi throughout the property, the non-smoking hotel has a hot tub. The hotel has a sun terrace. Popular points of interest near The Mermaid & The Alligator include Ernest Hemingway Home and Museum, Duval Street and Southernmost Point. Key West International Airport is 1.9 miles from the property.

Guest Reviews:

- "One of bed B&B we have ever stayed in." - "We will come again!!!" - "Key West in Summer is good to miss the big winter crowds" - "I’d stay there again. It’s a quiet place close to everything but not too close. It’s adorable , the breakfast was good a" - "It was very good."

The Conch House Heritage Inn
Hotels

This adult-only Conch House Heritage Inn offers accommodations in Key West with breakfast included and complimentary mimosas. Every room at this bed and breakfast is air conditioned and is fitted with a flat-screen TV. The rooms come with a private bathroom equipped with a shower. For your comfort, you will find bath robes and free toiletries. A TV is featured. You will find luggage storage space at the property. Ernest Hemingway Home and Museum is 1312 feet from The Conch House Heritage Inn, while Duval Street is 1640 feet away.

Guest Reviews:

- "It was like being home away from home." - "A wonderful visit to Key Wedt!!" - "We really enjoyed our stay - it was a highlight of our trip to The Keys." - "Good value, charming accommodation in a brilliant location." - "all great but a 711 Breakfsat"

Ella's Cottages - Key West Historic Inns
Hotels
Key West, FL, USA

Offering a heated outdoor pool, this boutique Ella's Cottages is located in Old Town Key West 2 minutes' walk from Duval Street. Free WiFi and a poolside continental breakfast are provided. A flat-screen cable TV, an en suite, and hardwood floors and furnishings are standard in all rooms and suites. All rooms have a mini fridge. Both rooms and suites include access to a tropical garden. The guest house is 1476 feet from Ernest Hemingway Home and Museum and 15 minutes' walk from the Sunset Pier. Higgs Beach is 1.2 mi away.

Guest Reviews:

- "Hot, relaxing and a lot of laughs" - "Pleasant and peaceful" - "Wonderful family time" - "Historic charm and pampering" - "Wonderful property, quaint rooms and friendly staff" - "wonderful" - "Perfect quiet spot but still super close to all the old town locations and restaurants. Would 100% recommend" - "Could not have had a better time than we had" - "Just perfect, we are going come back" - "Ella’s Cottages was walkable to so much! Beautiful property."

Winslow's Bungalows - Key West Historic Inns
Hotels
Key West, FL, USA

Located in Key West, Florida, Winslow's Bungalows features 3 swimming pools, free WiFi access, and complimentary continental breakfast. The Southernmost Point is just 0.6 mi away, and Duval Street is 2461 feet from the inn. A flat-screen cable TV comes standard in each room at Winslow's Bungalows. All rooms feature a small refrigerator. Each private bathroom also comes with a hairdryer and free toiletries. Paths through landscaped gardens and a sun terrace with lounge chairs can be enjoyed at Winslow's Bungalows. Other facilities offered include 3 outdoor pools, hammocks and swings. On-site parking is available for a surcharge. Smathers Beach and Fort Zachary Taylor State Park are an 8-minute drive from Winslow's Bungalows. Guests will be just 8 minutes’ walk from The Ernest Hemingway Home and Museum and 10 minutes' walk from Key West Butterfly and Nature Conservatory.

Guest Reviews:

- "Perfect" - "Loved our stay here at Winslows bungalow" - "I loved it here and will be returning!" - "Good stay with great decor of rooms and grounds." - "Beautiful rooms and beautiful views and the place is so nice we will Definitely be going back !!!!!" - "Beautiful Winslow Property" - "Awesome place to stay" - "all in all very nice, friendly staff, comfortable room and a nice breakfast" - "Better can be .Will be back Asap."

Key West Historic District Hotels with Parking

best hotels in Key West Historic District
8.5
187 reviews
From $399

Ella's Cottages offers hassle-free parking solutions for guests, ensuring a seamless arrival and departure experience. With secure on-site parking, you can rest assured that your vehicle is safe as you explore the vibrant streets of Key West. Enjoy easy transit to local attractions without the stress of finding a spot, allowing you to focus on making the most of your stay in this picturesque destination.

best hotels in Key West Historic District
9.1
31 reviews
From $907

Seamless arrival is a priority at this tranquil retreat, where secure parking options provide peace of mind during your stay. Enjoy hassle-free transit as you explore the attractions of Key West, knowing your vehicle is safely accommodated. The Conch House Heritage Inn ensures that every detail contributes to a smooth experience, allowing you to focus on enjoying your getaway without the stress of parking concerns.

best hotels in Key West Historic District
8.6
1276 reviews
From $318

At Winslow's Bungalows, guests enjoy seamless arrival with convenient on-site parking available for a surcharge, ensuring hassle-free transit throughout their Key West adventure. The well-organized parking facilities provide peace of mind, allowing visitors to explore local attractions without worrying about vehicle security. Enjoy a stress-free experience as you easily access popular spots like Smathers Beach and Duval Street, making your stay as effortless as possible.

best hotels in Key West Historic District
8.4
715 reviews
From $270

For a seamless arrival at Paradise Inn - Adult Exclusive, enjoy hassle-free parking options that ensure your peace of mind. Secure parking facilities provide safe transit for your vehicle, allowing you to focus on relaxation and socializing. Additional services make your first steps into this captivating destination smooth and effortless. Conveniently located near all local attractions, you can park your car and immerse yourself in the vibrant culture of Key West instantly.

Key West Historic District Hotels with Entertainment

best hotels in Key West Historic District
9.3
148 reviews
From $2197

Dive into the vibrant nightlife of Key West at this lively oasis, where every evening is a celebration! With its stunning outdoor swimming pool and a sun terrace perfect for mingling, guests can enjoy a refreshing dip before heading out to explore nearby hotspots like Duval Street and Mallory Square. The Mermaid & The Alligator is your gateway to exhilarating activities, all while offering cozy accommodations and a hot tub to unwind after an unforgettable night of fun!

best hotels in Key West Historic District
9.1
31 reviews
From $907

Dive into the vibrant nightlife of Key West at this adult-only haven that exudes energy and charm. Just steps away from Duval Street, guests can easily explore lively bars, eclectic restaurants, and exciting activities that keep the party going. Each morning starts with a complimentary breakfast and mimosas, setting the tone for an exhilarating day ahead. With a refreshing pool to unwind in, it's the perfect base for social butterflies eager to experience the best of the island's entertainment scene.

best hotels in Key West Historic District
8.4
715 reviews
From $270

Unleash your inner party animal at this vibrant adult-exclusive oasis in Key West! With a lively atmosphere and proximity to electrifying nightlife, guests can dive into an array of activities just moments away. Enjoy complimentary wine and cheese hour while mingling with fellow travelers, then take a dip in the outdoor pool or relax in the hot tub. Embrace the energy of local bars and live music venues, ensuring an unforgettable experience brimming with excitement.

Key West Historic District Pet Friendly Hotels

best hotels in Key West Historic District
8.6
1276 reviews
From $318

Winslow's Bungalows warmly welcomes furry family members, ensuring that no one gets left behind during your Key West getaway. With pet-friendly amenities and nearby scenic walks, both pets and owners can enjoy the beauty of the area together. Relax in spacious accommodations that cater to your pet's needs while enjoying the lush surroundings. This is the perfect destination for families seeking a memorable escape with their beloved pets in tow.

best hotels in Key West Historic District
8.5
187 reviews
From $399

Bringing your furry companions along is a breeze at Ella's Cottages, where every pet is welcomed with open arms. With convenient pet amenities and beautiful nearby walks, your whole family—including pets—can enjoy the charm of Key West together. Experience the joy of creating shared adventures in a setting that understands no family member should be left behind.

Key West Historic District Family Friendly Hotels

best hotels in Key West Historic District
8.5
187 reviews
From $399

At Ella's Cottages, families can unwind in a safe and inviting environment designed with children in mind. The on-site kids' club provides engaging activities, ensuring parents enjoy stress-free bonding time while their little ones are entertained. With spacious accommodations and easy access to nearby attractions, your family will create lasting memories in this charming Key West haven, where comfort and safety come first.

best hotels in Key West Historic District
8.6
1276 reviews
From $318

Families will find a welcoming retreat at Winslow's Bungalows, where safety and fun come together for stress-free bonding. The on-site kids' club allows little ones to engage in supervised activities, giving parents peace of mind. With lush gardens and three swimming pools, children can enjoy endless outdoor play while parents relax knowing their family is secure in this nurturing environment. Create lasting memories in the heart of Key West, where every detail caters to family needs.

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