Where to Stay in Key West

Most popularly known for Ernest Hemingway, the legendary American Novelist, who fell in love with the island and called it home, Key West is a four-mile-long and two-mile-wide island city in the Florida Keys archipelago. One of the most exclusive places in the United States of America, the island city is characterized by its laid-back atmosphere, artistic scene, and Concho-style houses.

More famous for its coral reefs than its beaches, Key West has an excellent number of recreational activities, water sports, and historic sights. Closer to Cuba than to Miami, the city benefits from a diverse ethnicity. Welcoming national and international visitors over a couple of centuries, Key West is a place to unwind and rediscover yourself. Scattered with quirky gravestones that read things like “I told you I was sick,” “I’m just resting my eyes,” and “Died from not forwarding that text message to 10 people,” the Key West Cemetery correctly sums up the city’s humorous and free-spirited character.

Let us now explore some of the popular neighborhoods in this wonderful island city so you can select where to stay in Key West on your visit.

Mallory Square

Mallory Square, Key West

Source: GagliardiImages / shutterstock

Mallory Square

The epicenter of Key West’s social and commercial activities, Mallory Square has welcomed visitors from all around the island and the world since the beginning of the 1820s. With numerous restaurants, museums, theatres, shops scattered around the square, this neighborhood is within an arm’s reach of several iconic landmarks on the island. The biggest draw of this area, however, is the sunset scene that unveils itself every evening at the historic Mallory Dock. Hundreds of spectators gather at the dock to see one of the most exquisite sunsets in the world, but that’s not all – acrobat performers, sword swallowers, musicians, flame tossing jugglers, and performers with their trained birds and animals gather together to make the evening even more exciting. Arrive here a couple of hours before sunset to experience the whole phenomenon.

Good for: All kinds of travelers.
Other Highlights: Key West Aquarium, Key West Shipwreck Museum, Fury Water Adventures Key West, Ripley’s Believe It or Not! Odditorium, and Audubon House & Tropical Gardens.

Hotel Recommendations:

  • Pier House Resort & Spa – Featuring a full-service spa and wellness center, an outdoor pool, and a private beach with instant access, Pier House Resort & Spa offers lavish guestrooms with exemplary amenities such as rain-style showers, tea/coffee maker, cable TV, and ensuite bathroom. Guests can choose one of the many restaurants and bars to enjoy their meal and cocktails. Perfect for all kinds of luxury travelers.
  • Margaritaville Key West Resort & Marina – This waterfront hotel located next to Key West Aquarium boasts an outdoor heated pool, a state-of-the-art fitness center, on-site water-sports facilities, and wonderfully-designed stylish guestrooms. Guests can enjoy a view of the pool or the marina from the comfort of their room. Great for all kinds of travelers.
  • Simonton Court Historic Inn & Cottages – An adult-only property with 4 on-site pools, a well-manicured garden area, a daily maid service, and a concierge, Simonton Court Historic Inn & Cottages is within minutes of many notable attractions on the island, including Mallory Square and Ernest Hemingway Home and Museum. Suitable for all kinds of travelers.

Old Town/ Key West Historic District

Key West Historic District

Source: Fotoluminate LLC / shutterstock

Key West Historic District

Key West Historic District, popularly known as the Old Town, is a designated U.S. historic district and is home to over 187 momentous buildings and 1 historic structure. Home of the island’s central business district and the highest concentration of tourist sites, the neighborhood approximately covers the western section of the island. Some of the notable landmarks and attractions in the area include Key West Aquarium, the Armory, and the legendary Sloppy Joe’s. The only public aquarium on the island and one of the oldest in Florida, Key West Aquarium comprises alligators, sharks, giant hermit crabs, and stingrays. Sloppy Joe’s, on the other hand, is the famous American Bar which was frequented by the likes of Ernest Hemingway and Havana Joe and is now listed on National Register of Historic Places.

Good for: All kinds of travelers.
Other Highlights:
Oldest House & Garden Museum, Mel Fisher Maritime Museum, St. Paul’s Episcopal Church, Mile Marker 0, Key West Cemetery, and Nancy Forrester’s Secret Garden.

Hotel Recommendations:

  • Old Town Manor – The pet-friendly, adult-only Old Town Manor welcomes its guests to enjoy well-appointed rooms which are fitted with modern facilities such as cable TV and DVD Player, free Wi-Fi, coffee machine, and private bathroom. Guests can lounge in the on-site garden or unwind themselves at the sun terrace. Suitable for solo travelers and couples.
  • Courtney’s Place Historic Cottages & Inns – A short walk from the beach, this historic property provides spacious, air-conditioned guestrooms and cottages equipped with up-to-date amenities. An on-site pool, a parking space, and barbecue facilities are available for the guests’ comfort and relaxation. Great for all kinds of travelers, including big groups of up to 8 members.
  • Old Town Suites – A stone’s throw away from the celebrated Ernest Hemingway Home and Museum, Old Town Suites features expansive, self-catering units equipped with tons of facilities. Guests can spend their day at the nearby beach or explore the Key West Butterfly and Nature Conservatory located within a few hundred meters from the property. Perfect for all kinds of travelers, including big groups of up to 5 members.

New Town

24 North Hotel Key West

Source: booking.com

24 North Hotel Key West

Situated North East of the Old Town neighborhood of Key West, New Town, is everything that its historic counterpart isn’t. Nonetheless, it is a good place to explore and stay if you plan to visit the island with your family and stay for a longer duration since the area is highly residential and is filled with typical Florida-style CBS houses, home improvement stores, and a shopping center. Covering the eastern part of Key West Island, this neighborhood allows you stay away from the touristy crowd of Old Town and Mallory Square but still be within a short distance, so you could have a fun evening anytime you want.

Good for: All kinds of travelers.
Other Highlights:
Key West Tropical Forest & Botanical Garden, East Martello Museum, Charterboat Row, and the Florida Keys Overseas Heritage Trail.

Hotel Recommendations:

  • 24 North Hotel Key West – Boasting an outdoor pool with lounge chairs, a sun terrace, and a poolside bar, 24 North Hotel Key West offers luxurious guestrooms and suites, most of which either overlook the pool or the ocean. The 24-hour front desk at the property can help arrange a free shuttle to visit the Old Town. Great for all kinds of travelers.
  • The Gates Hotel Key West – Featuring an outdoor pool with a pool bar, an on-site restaurant, and hourly shuttle service to Key West Historic District, the Gates Hotel Key West offers excellent guestrooms with brilliant amenities such as cable TV, free Wi-Fi, refrigerator, and ensuite bathroom with free toiletries. Suitable for all kinds of travelers.
  • Havana Cabana Key West – A 5 minutes’ drive from Key West International Airport, Havana Cabana Key West spoils its guests with world-class facilities such as an outdoor pool with lounge chairs, a poolside bar, a great fitness center, and free parking. A complimentary breakfast is served daily. Perfect for all kinds of luxury travelers.

Smathers Beach

Smathers Beach, Key West

Source: Tono Balaguer / shutterstock

Smathers Beach

The largest public beach on the island, Smathers Beach is located along the Atlantic Ocean and is roughly half a mile long. Beginning at the iconic Mile Marker Zero, the beach covers the southern part of the island. Welcoming over 150,000 visitors annually, the area is extremely popular and packed during spring break. Made famous by long-distance swimmer Diana Nyad, who swam 110 miles from Havana, Cuba to the Smathers Beach in 2013 and became the first person ever to swim the distance without a shark cage. The coconut tree-lined coastline offers plenty of facilities to visitors, including bathrooms, chairs and umbrellas, picnic areas, food trucks, and jet ski rental shops.

Good for: All kinds of travelers.
Other Highlights:
The Key West Nature Preserve, Fort East Martello Museum, Bayview Park, Southernmost Point, and Edward B. Knight Pier.

Hotel Recommendations:

  • Sheraton Suites Key West – A couple of minutes’ walk from the beach, Sheraton Suites Key West is an all-suite hotel with superb, self-catering units set within a serene, tropical atmosphere. Guests can unwind themselves with a refreshing cocktail at the bar located next to the lagoon pool and groove to the tunes of Caribbean music. Perfect for all kinds of luxury travelers, including groups of up to 5 members.
  • Best Western Key Ambassador Resort Inn – Comprising over 7 acres of tropical setting and ultimate hospitality, Best Western Key Ambassador Resort Inn charms its visitors with its heated oceanfront pool that directly overlooks the Atlantic Ocean. Surfing, fishing, and diving are popular recreational activities in the area. Great for all kinds of travelers.
  • Hyatt Residence Club Key West, Windward Pointe – Boasting a year-round outdoor pool and hot tub, this fabulous property offers fully-equipped, self-catering apartment units within a kilometer from Key West International Airport. Complimentary Wi-Fi is available throughout the property. Suitable for families and big groups.

Duval Street

Duval Street, Key West

Source: Fotoluminate LLC / shutterstock

Duval Street

One of the most prominent districts on the island, the street runs north to south from the Gulf of Mexico to the scintillating Atlantic Ocean. Though not more than a mile in area, Duval Street is arguably the main drag of Key West – think an endless diversity of restaurants, mind-blowing shops, and world-famous pubs. Hogs Breath Salon, in service for the last 25 years, is one those legendary water holes that you absolutely can’t miss on your visit to the neighborhood. Alternatively, you could hang out with locals at the century-old Green Parrot bar and enjoy some of the finest touring bands. If you are feeling adventurous, head over to Mel Fisher Maritime Museum to gawk at the motherload unearthed during the discovery of the sunken ship Spanish Galleon Nuestra Senora de Atocha, an event that made Mel Fisher the greatest treasure hunter in the world in 1985.

Good for: All kinds of travelers.
Other Highlights:
The Ernest Hemingway Home and Museum, Key West Lighthouse, The Basilica of St. Mary Star of the Sea, Key West Firehouse Museum, Key West Cemetery, Ripley’s Believe It or Not! Odditorium, and Oldest House & Garden Museum.

Hotel Recommendations:

  • Avalon Bed and Breakfast – Within a 10 minutes’ walking distance from the beach, Avalon Bed and Breakfast is one of the most sought-after properties in Duval Street. The fascinating guestrooms here come with canopy net extra-large double beds, cable TV, and hardwood/parquet floors. A small outdoor pool and the hotel’s proximity to the famous Barefoot Billy’s Watersports makes it a top choice among visitors. Great for all kinds of travelers.
  • Southernmost Point Guest House – A minutes’ stroll from the beach, Southernmost Point Guest House provides its guests with barbecue facilities, a well-manicured garden space with seating area, and an outdoor pool. A complimentary American breakfast is available every morning and, in the evenings, wine is served gratis to adult guests. Suitable for all kinds of travelers
  • Douglas House – A couple of minutes’ walking distance from the Ernest Hemingway Home and Museum, Douglas House is an adult-only, pet-friendly property with excellent guestrooms and suites. Facilities at the hotel include an outdoor pool, a well-maintained tropical garden, and complimentary Wi-Fi. Perfect for all kinds of adult travelers, including big groups of up to 5 members.

Bahama Village

Bahama Village, Key West

Source: Deatonphotos / shutterstock

Bahama Village

Once ill-reputed for its crime rate, Bahama Village is a sub-neighborhood of the larger Old Town district known for its Bahamian ancestry and its popular flea market. Comprising the island’s only public swimming pool, the area covers a 16-block radius and consists of various restaurants, shops, and free animals roaming on the streets (such as chicken families). A former primary black neighborhood, Bahama Village is now home to some of the greatest diners on the island, including La Creperie. The famous flea market can be found at the entrance of Bahama Village on Petronia Street – this is where you should shop for Key West souvenirs.

Good for: All kinds of travelers.
Other Highlights:
St. Paul’s Episcopal Church, Nancy Forrester’s Secret Garden, The Key West Theater, Mile Marker 0, and Mel Fisher Maritime Museum.

Hotel Recommendations:

  • La Concha Hotel & Spa – Boasting a Tiki Bar, an outdoor pool, a modern fitness center, a rooftop spa and wellness center, and an exclusive wine bar, the historic La Concha Hotel & Spa offers marvelous guestrooms and suites with premium facilities such as extra-large double beds with pillow-top mattresses, 42-inch flat-screen TV with cable and CD Player, and ensuite bathroom with free toiletries. A complimentary American breakfast is served daily. Perfect for all kinds of luxury travelers.
  • Pegasus International Hotel – A short walk from the beach, this classy, Art Deco hotel offers a stunning pool with a huge sun terrace and a hot tub and a 24-hour front desk. Guests at the property enjoy a wonderful stay at one of the splendid rooms equipped with cable TV, free Wi-Fi, and a seating area. Great for all kinds of travelers.
  • Ambrosia Key West – A short walk from the innumerable cafes and art galleries of Duval Street, Ambrosia Key West invites its guests to start their day with a sumptuous hot breakfast and a rejuvenating swim at one of their two swimming pools. This pet-friendly property also has a lush green space and a hot tub. Perfect for all kinds of travelers.

Historic Seaport

Historic Seaport, Key West

Source: Chuck Wagner / shutterstock

Historic Seaport

Historic Seaport, also referred to as Key West Historic Seaport by some, is where you go for an authentic Key West island experience. Characterized by unique bars, one-of-a-kind art galleries and boutiques, historic museums elaborating the island’s history, and, of course, the harbor walk waterfront, the seaport has been a significant global maritime trading base for over a couple of centuries. Home to several historic ships, including the 1939 Schooner Western Union, the area is your perfect base to experience some world-class sailing and diving in Key West. If you have the time and luxury, it is a great idea to book one of the historic yachts for a day’s sailing and then take a catamaran to visit the reefs on the following day.

Good for: All kinds of travelers.
Other Highlights:
Key West Bight, Flagler Station Oversea Railway Historeum, Sebago Watersports, and Reef Relief.

Hotel Recommendations:

  • Seaport Inn – Set in the center of Key West Historic Seaport neighborhood, the Seaport Inn offers well-appointed studios and suites fitted with amenities such as cable TV, free Wi-Fi, barbecue facilities, and a balcony (in selected rooms). Mallory Square and Key West Aquarium are within a walking distance from the property. Suitable for all kinds of travelers.
  • Island City House – Featuring an outdoor pool, a well-manicured garden, and Victorian-style guestrooms, Island City House offers close proximity to Sunrise Pier and Key West Museum of Art & History. The historic hotel also provides laundry and luggage storage facilities and complimentary Wi-Fi. Perfect for all kinds of luxury travelers, including big groups of up to 6 members.
  • The Marker Waterfront Resort – One of the most exclusive oceanfront resorts in Key West, the Marker Waterfront Resort boasts 3 outdoor pools, a state-of-the-art fitness center, a well-equipped business center, an on-site restaurant and bar, and water-sports facilities. The property is a short walk from Key West Sailing Adventure. Great for all kinds of travelers.
Where to stay: Best Hotels in Key West, Florida (FL)
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List of Image Sources

Where to Stay in Key West:

Mallory Square, Key West

  • Mallory Square: GagliardiImages / shutterstock
  • Key West Historic District: Fotoluminate LLC / shutterstock
  • 24 North Hotel Key West: booking.com
  • Smathers Beach: Tono Balaguer / shutterstock
  • Duval Street: Fotoluminate LLC / shutterstock
  • Bahama Village: Deatonphotos / shutterstock
  • Historic Seaport: Chuck Wagner / shutterstock