Best Areas to Stay in Key West, Florida

The Key West Historic Seaport District is home to dozens of restaurants, bars, and things to do.

Located at the northwestern edge of the island, Key West’s historic seaport has long been a hub of activity, and nowadays it is considered the tourist heart of the city.

This area, Key West’s birthplace, is home to some of the city’s most important landmarks, such as Mallory Square, Simonton Beach, the Key West Shipwreck Museum, Mel Fisher Maritime Museum, Key West Museum of Art & History, and the Key West Aquarium.

Not far, you’ll find the Truman Little White House, President Harry S Truman’s winter residence, now a museum.

Around the Key West Historic Seaport, there are dozens of restaurants offering some of the freshest seafood in Key West. The area is also known for its many nightlife options, with several bars, cocktail lounges, and nightclubs.

If you’re looking for shopping, The Key West Historic Seaport District is home to some of the best boutiques and art galleries in South Florida.

The boats to Dry Tortugas, as well as other island hopping, charter fishing, boating, and water sports excursions, leave from the Historic Seaport.

The Key West Historic Seaport District is the best area to stay in Key West thanks to its perfect combination of tourist attractions, historical sights, nightlife, shopping, and transportation options.

Duval Street is Key West’s main commercial area.

This 1.25 mile-long street runs north-to-south, from the Gulf of Mexico to the Atlantic Ocean, and gets its name from William Pope Duval, the first territorial governor of Florida.

Considered Key West’s commercial core, this thoroughfare is home to many restaurants, shops, world-famous pubs, and tourist attractions.

At Duval’s north end, you’ll find the Historic Seaport and Mallory Square area. This part of town is known for its vibrant atmosphere and is the tourist heart of the island. The City of Key West and Duval Street share their beginning along this deep harbor waterfront.

Duval Street is also the main nightlife area in Key West, with many tourists engaging in the “Duval Pub Crawl.” Many famous restaurants and bars, including Sloppy Joe’s, Jimmy Buffett’s Margaritaville, Fogarty’s Restaurant, Bar and Bakery, The Flying Monkeys Bar, and The Bull and Whistle, are located along this lively street.

Duval Street is also home to the city’s LGBT Quarter. Many nightlife and accommodation establishments along this street are gay-friendly or gay-owned, and Rainbow flags are easy to spot.

The Hemingway Home and Museum, located on nearby Whitehead Street, was the residence of American writer Ernest Hemingway in the 1930s.

One block west of Duval’s southern terminus is the buoy marker designating the southernmost point in the United States. Nearby, you’ll find the Southernmost House, a Victorian mansion built in 1896.

Duval is the best area to stay in Key West for nightlife.

The Key West Historic District, also known as Old Town Key West is a U.S. historic district encompassing approximately 5400 acres and containing 2489 historic buildings and structures.

Old Town Key West covers roughly all of the western half of the island and it is where the central business district and the majority of the tourist attractions are located.

The north side of the Key West Historic District is dominated by the Historic Seaport, while its western edge is home to the lively Duval Street neighborhood.

As you move east from Duval, Old Town Key West is actually a quiet area, characterized by its historical mansions, palm tree-lined residential streets, and secluded inns and B&Bs.

Other than the attractions near Duval and the Historic Port, Old Town Key West is home to the Basilica of St. Mary Star of the Sea, the Key West Cemetery, the Key West Firehouse Museum, Nancy Forrester’s Secret Garden, and Bayview Park.

Located west of Duval, the Bahama Village covers a 16-block area bounded by Fort, Louisa, Southard, and Whitehead streets.

This diverse neighborhood is known for its Caribbean heritage and gets its name from the first black Bahamian settlers who arrived in Key West in the 19th century. Today, the Village is the place to go for authentic Bahamian cuisine and culture.

The Bahama Village is also famous for its music scene, with island-inspired rhythms like reggae, calypso, junkanoo, and dancehall blasting from its many bars and clubs.

This historic district is also home to a few attractions, including the Key West Hemingway House, the Truman Little White House, and the Key West Old Lighthouse.

About a mile west from the Bahama Village lies Fort Zachary Taylor Historic State Park, a state park with nature trails, a cafe, and a historic fortress. Fort Zachary Taylor Historic State Park Beach is considered one of the finest in Key West and is ideal for swimming, snorkeling, and fishing.

As we mentioned above, Key West is primarily known as a beach destination.

In fact, chances are that if you landed on this post about the best areas to stay in Key West, it’s because you’re traveling to this lovely Florida island to bask in the sun and swim in its incredible white sand and turquoise water beaches.

If that’s the case, you’ll be happy to know that some of the best public beaches on the island of Key West are located on its southern coast.

As you move east from Fort Zachary Taylor Historic State Park Beach you’ll come across Straw Hat Beach, a rocky beach located next to the actual southernmost point ìn the contiguous United States.

Not far lies Dog Beach, a small, secluded beach with palms trees where dogs are allowed to go unleashed. Dog Beach is popular among surfers.

Higgs Memorial Beach, probably the nicest central beach in Key West, includes a couple of piers, plus several monuments documenting the site of an African Refugee Cemetery.

Next to it, Rest Beach is popular for shell searching.

And finally, you have Smathers Beach. The longest and most tranquil beach in Key West, this large stretch of sand offers all kinds of services and is close to some of the best resorts on the island’s south side.

South Key West is the best area for a beach holiday in Key West.

New Town Key West encompasses the whole eastern side of the island, from White Street eastward to the channels separating Key West from Stock Island and Cow Key.

As its name may imply, the New Town was developed in fairly recent times and it is where most of the Kew West locals live, work and shop.

The fact that it is a more local alternative to the (sometimes overly) touristy areas around the Old Town is the main reason to choose New Town as the best area to stay in Key West, especially if you’re after a quiet holiday away from the crowds.

New Town Key West is complete with supermarkets, small shops, local and chain restaurants, and a few malls, and it’s a great alternative if you have a car.

The island’s northeastern edge, close to Stock Island, is home to the Northside Resort. This tourist development has several mid-range and high-end resorts and is close to some local attractions like the Key West Tropical Forest & Botanical Garden and a few marinas where you can rent boats or hire excursions.

Key West’s Southside Resort area is located on the southeastern edge of the island, next to the airport.

This tourist development is home to some big-name chain resorts and a few local hotels and privately-owned apartments.

Some of the attractions in this area include Fort East Martello Museum, an 1800s brick fortress and local history museum, a few beaches, and lagoons. This is also where the airport and the Greyhound Station are located.

Key West International Airport occupies the southern half of the island’s east side. This local airport offers a wide range of domestic connections to the US South and the East Coast.

Located directly east of Key West lies Stock Island.

This lovely island offers a quiet alternative to the crowded streets of the Old Town and it is one of the best areas to stay in Key West if you’re looking for a laid-back holiday.

Safe Harbour Marina, located in the south of Stock Island, a 10-min drive to downtown Key West, offers docking services, boat rentals, recreational facilities, and several restaurants and bars.

Sock Island’s north side is also home to the Key West Tropical Forest & Botanical Garden and the Key West Golf Club.