Find hotels in Old Town Key West, Key West from $207

While Old Town Key West is generally considered the prime location for visitors, other areas offer similar convenience and character for specific preferences.

For those seeking a slightly more residential feel with easy access to Old Town's attractions, the Truman Annex neighborhood is an excellent choice. Situated at the western end of Old Town, it's a gated community known for its beautifully maintained homes, manicured gardens, and a quieter atmosphere. It's close to attractions like the Harry S. Truman Little White House and Fort Zachary Taylor Historic State Park, offering a blend of history and natural beauty. This area is particularly well-suited for couples seeking a peaceful retreat while remaining within a short walk or bike ride of Duval Street.

Another option for travelers who appreciate a balance of tranquility and accessibility is the area just east of Old Town, often referred to as the Casa Marina neighborhood. This area is characterized by its grander homes, larger lots, and a relaxed, upscale feel. It's home to some of Key West's most luxurious accommodations and provides easy access to the less crowded beaches on the south side of the island.

For highly-rated hotels in Old Town Key West, travelers consistently recommend The Gardens Hotel, Southernmost House, The Reach Key West, Curio Collection by Hilton, Casa Marina Key West, Curio Collection by Hilton, and Southernmost Beach Resort and Guesthouses.

The 4-star Gardens Hotel, with an outstanding 9.8 rating, is celebrated for its beautiful, clean rooms and friendly staff. Guests enjoy the wonderful breakfast and the beautiful garden surroundings. It is also conveniently located near Simonton Beach and the Key West Butterfly and Nature Conservatory.

Another excellent choice is the 4-star Southernmost House, rated 9.4. This hotel is praised for its helpful staff, beautiful and clean rooms, and amazing pool. Its great location places it very close to the Key West Butterfly and Nature Conservatory and within easy reach of Mallory Square.

The 4-star The Reach Key West, Curio Collection by Hilton, with an 8.4 rating, offers nice and clean rooms and an excellent location. Guests appreciate the friendly staff and the wonderful pool. It is located very close to Simonton Beach and the Key West Butterfly and Nature Conservatory.

Casa Marina Key West, Curio Collection by Hilton, a 4-star hotel with an 8.4 rating, provides beautiful and spacious rooms. Travelers frequently mention the friendly staff and the great amenities, including a pool. This hotel is also close to Simonton Beach and the Key West Butterfly and Nature Conservatory.

Finally, the 4-star Southernmost Beach Resort and Guesthouses, rated 8.8, features nice and clean rooms and helpful staff. Guests often praise the great location and excellent service. It is ideally situated near the Key West Butterfly and Nature Conservatory and Simonton Beach.

For family-friendly hotels in Old Town Key West, consider the Santa Maria Suites, Casa Marina Key West, Curio Collection by Hilton, The Reach Key West, Curio Collection by Hilton, Southernmost Beach Resort and Guesthouses, and Southwinds Motel.

The 4-star Santa Maria Suites, with an exceptional 9.6 rating, is highly praised for its spacious and beautiful rooms. Families will appreciate amenities such as a sofa bed, free cribs, and a resort-inclusive outdoor pool with sun loungers and a poolside bar. It is conveniently located near Simonton Beach and the Key West Butterfly and Nature Conservatory.

Another excellent option is the 4-star Casa Marina Key West, Curio Collection by Hilton, rated 8.4. This hotel offers connecting rooms, sofa beds, a pool, and free cribs, along with on-site babysitting services and child-friendly window designs. Guests frequently highlight the friendly staff, great location, and beautiful, large rooms. It is close to Simonton Beach and the MLK Community Pool & Community Center.

The 4-star The Reach Key West, Curio Collection by Hilton, also rated 8.4, provides amenities like child-friendly window designs, connecting rooms, free cribs, and sofa beds. Guests consistently mention the friendly staff, nice and clean rooms, and excellent location. The hotel is situated near Simonton Beach and the Key West Butterfly and Nature Conservatory.

The 4-star Southernmost Beach Resort and Guesthouses, with an 8.8 rating, is a great choice offering a pool, child-friendly window designs, and free cribs, along with beach and ocean views. Located very close to the Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center, guests often praise the friendly staff and clean rooms.

As another option, the Southwinds Motel, rated 8.8, offers amenities such as sofa beds, free cribs, a gated pool, highchairs for children, and complimentary continental breakfast. Travelers appreciate the comfortable and clean rooms, friendly staff, and convenient location near Simonton Beach and the Key West Butterfly and Nature Conservatory.

For excellent spa hotels in Old Town Key West, consider the Casa Marina Key West, Curio Collection by Hilton, the Southernmost Beach Resort and Guesthouses, The Reach Key West, Curio Collection by Hilton, or the Opal Key Resort & Marina, Key West.

The 4-star Casa Marina Key West, Curio Collection by Hilton, with an 8.4 rating, offers a full-service spa with deep tissue massage, body wraps, body scrubs, and facial treatments. They also provide couples treatment rooms and massages on the beach. It is conveniently located about 0.7 miles from the Ernest Hemingway Home and Museum.

Another great option is the 4-star Southernmost Beach Resort and Guesthouses, rated 8.8. This hotel features a full-service spa available daily, offering facial treatments, massage, and couples treatment rooms. It is situated approximately 0.4 miles from the Ernest Hemingway Home and Museum.

The 4-star The Reach Key West, Curio Collection by Hilton, also rated 8.4, provides a full-service spa that includes hot stone massage, deep tissue massage, and a variety of other treatments. The hotel is about 0.5 miles from the Ernest Hemingway Home and Museum.

Finally, the 4-star Opal Key Resort & Marina, Key West, boasting a 9.0 rating, offers an onsite spa and massage services, alongside an outdoor resort-inclusive pool and a poolside bar. It is very close to the Harry S. Truman Little White House, only 0.2 miles away.

Two highly-regarded beach resorts in Old Town Key West that travelers consistently love are the Casa Marina Key West, Curio Collection by Hilton, and The Reach Key West, Curio Collection by Hilton. Another popular option is the Coconut Beach Resort.

The 4-star Casa Marina Key West, Curio Collection by Hilton, rated 8.4, offers a private beach and ocean views, making it ideal for those seeking relaxation by the sea. Guests frequently praise the friendly and amazing staff, the beautiful and big rooms, and the great amenities, including a full-service spa with various treatments such as deep tissue massage and body wraps. It is conveniently located near Simonton Beach, just 0.2 miles away.

Also a 4-star property with an 8.4 rating, The Reach Key West, Curio Collection by Hilton, features a private beach and ocean views. Travelers appreciate the excellent location, friendly staff, and the nice, clean rooms. The resort also boasts an excellent outdoor pool with sun loungers and a poolside bar, great for enjoying the Florida sunshine. It is situated just 0.1 miles from Simonton Beach.

The Coconut Beach Resort, with an impressive 9.0 rating, also offers a private beach and ocean views. Guests often mention the nice pool and the friendly staff. This resort provides an outdoor pool with amenities like pool toys and umbrellas, making it a great choice for families or those looking to relax by the water. It is conveniently located 0.1 miles from Simonton Beach.

For hotels in Old Town Key West that offer complimentary breakfast, consider the Almond Tree Inn Hotel - Adults Only, Orchid Key Inn - Adults Only, The Gardens Hotel, Key West Villas, or The Conch House Heritage Inn.

The 3.5-star Almond Tree Inn Hotel - Adults Only, boasting a great 10.0 rating, provides a free continental breakfast. Guests frequently praise the friendly and helpful staff, comfortable and clean rooms, and the excellent breakfast. Its location is considered perfect, and the outdoor pool is described as nice and clean. It is conveniently located near Simonton Beach and the Key West Butterfly and Nature Conservatory.

Another excellent option is the 3.5-star Orchid Key Inn - Adults Only, rated 9.8. This hotel also offers a free continental breakfast, and guests consistently highlight the friendly and amazing staff, beautiful and clean rooms, and the great breakfast. The convenient location is also a key feature, and it includes an outdoor pool with a poolside bar.

The 4-star The Gardens Hotel, with a 9.8 rating, provides a free cooked breakfast. Travelers appreciate the beautiful and clean rooms, friendly staff, and the wonderful breakfast. The central location is also a major draw, and guests particularly enjoy the beautiful garden surroundings.

Key West Villas, a 3.5-star accommodation rated 9.8, offers a free continental breakfast. Guests frequently comment on the friendly and professional staff, great amenities and facilities, and the enjoyable hot tub. Its location is considered perfect, and it also includes free WiFi.

Finally, The Conch House Heritage Inn, a 3.5-star hotel with a 9.8 rating, includes a free continental breakfast. Guests often praise its great location, wonderful service, and the consistently friendly staff. It also features a private outdoor pool with sun loungers.

For top pet-friendly hotels in Old Town Key West, consider The Gardens Hotel, Winslow's Bungalows - Key West Historic Inns, Ella's Cottages - Key West Historic Inns, Lighthouse Hotel - Key West Historic Inns, and Opal Key Resort & Marina, Key West.

The 4-star Gardens Hotel, with an outstanding 9.8 rating, warmly welcomes pets and provides food and water bowls, specifically for dogs. Guests frequently praise the beautiful and clean rooms, the friendly staff, and the central location. It is also conveniently located near Simonton Beach and Mallory Square.

Another excellent choice is the 4-star Winslow's Bungalows - Key West Historic Inns, rated 9.2. This hotel is pet-friendly, providing food and water bowls, and features an outdoor resort-inclusive pool with a poolside bar and sun loungers. Guests consistently highlight the friendly staff, delicious breakfast, and comfortable rooms, all within a superb and convenient location.

Ella's Cottages - Key West Historic Inns, a 3.5-star hotel with a 9.4 rating, also welcomes pets and offers complimentary continental breakfast. Customers often comment on the friendly staff, comfortable rooms, and central location.

The 3.5-star Lighthouse Hotel - Key West Historic Inns, with a 9.0 rating, is another pet-friendly option that includes free continental breakfast. Guests appreciate the friendly staff, clean rooms, and great location, which is close to the MLK Community Pool & Community Center and Key West Butterfly and Nature Conservatory.

Finally, the 4-star Opal Key Resort & Marina, Key West, rated 9.0, is pet-friendly and specifically welcomes dogs. This resort offers an outdoor resort-inclusive pool with a poolside bar. Its location near Mallory Square is frequently mentioned as superb by guests, who also praise the great staff and spacious rooms.

For top boutique hotels in Old Town Key West, consider the Almond Tree Inn Hotel - Adults Only and the Orchid Key Inn - Adults Only.

The 3.5-star Almond Tree Inn Hotel - Adults Only boasts an exceptional 10.0 rating. Guests frequently praise the friendly and helpful staff, the comfortable and clean rooms, and the great location. This hotel offers a complimentary continental breakfast, an outdoor pool with sun loungers, and a poolside bar. It is conveniently situated just 0.1 miles from the Ernest Hemingway Home and Museum.

Another excellent choice is the 3.5-star Orchid Key Inn - Adults Only, which has a 9.8 rating. Travelers consistently praise the amazing staff, the beautiful and clean rooms, and the convenient location. Similar to the Almond Tree Inn, it provides a free continental breakfast, an inviting outdoor pool, and a poolside bar. It is also just 0.1 miles from the Ernest Hemingway Home and Museum, making it ideal for exploring this popular attraction.

For a romantic getaway in Old Town Key West, consider The Gardens Hotel or Orchid Key Inn - Adults Only.

The 4-star Gardens Hotel, with a superb 9.8 rating, is known for its elegant amenities including private pools, fireplaces, and rainfall showerheads. Guests can enjoy couples dining and a selection of premium bedding and designer toiletries. Its central location places it just 0.2 miles from the Ernest Hemingway Home and Museum.

Another excellent choice for couples is the 3.5-star Orchid Key Inn - Adults Only, also rated 9.8. This hotel offers a complimentary continental breakfast, an outdoor pool with a poolside bar, and free toiletries. It is conveniently located near the Ernest Hemingway Home and Museum, just 0.1 miles away. Guests frequently praise the friendly staff and beautiful, clean rooms.

For excellent hotels in Old Town Key West near the Key West Historic Seaport, consider The Gardens Hotel or H2O Suites - Adults Only.

The 4-star The Gardens Hotel, with an outstanding 9.8 rating, offers a luxurious experience. Guests frequently praise its beautiful and clean rooms, the friendly and kind staff, and its central location. The hotel features a pool, champagne service, and a restaurant with garden views, making it a wonderful retreat.

Another highly-rated option is H2O Suites - Adults Only, a 3.5-star hotel with a 9.8 rating. This hotel is celebrated for its beautiful and clean rooms, excellent staff, and wonderful amenities. It is conveniently located near Simonton Beach and the Key West Butterfly and Nature Conservatory, offering easy access to local attractions.

The best time to go to Old Town Key West is generally from March to May, or during the shoulder seasons of late November to early February.

During the spring months of March to May, the weather is pleasantly warm with lower humidity, making it ideal for exploring the historic streets and enjoying outdoor activities. This period avoids the peak crowds and higher prices of the winter season, offering a more relaxed experience for couples looking for a romantic getaway without the intense summer heat.

The late fall and early winter months, specifically late November to early February, also offer comfortable temperatures and a festive atmosphere. While it's a popular time, especially around holidays, the weather is excellent for walking tours, enjoying the waterfront, and experiencing the unique charm of Old Town.

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Old Town Key West.

Prices for hotels in Old Town Key West often vary, but you can find a great deal from $207 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.