Key West’s neighborhoods are as diverse as the people who call the island home. To help you make the most of your time in Key West, we’re breaking down the most frequented neighborhoods, from iconic Old Town to charming Bahama Village. Before you know it, you’ll be so versed in Key West, you just might be mistaken for a local. Here’s a rundown of the neighborhoods of Key West, with highlights of each to give you a feel for the area.
Old Town / Historic District / Historic Seaport
Comprising roughly the western half of the island, Key West’s Historic District is where a majority of the tourist attractions are located. Points of interest include Mallory Square, Duval Street, the famous Historic Seaport and boardwalk, Ernest Hemingway House, Key West Lighthouse, iconic bars like Captain Tony’s Saloon and Sloppy Joe’s, and impressive turn-of-the-century architecture. Guests of 24 North Hotel can enjoy a ride to Old Town aboard our air-conditioned shuttle - just show the driver your key!
Within Old Town, you’ll also find the ‘Truman Annex’ enclave, an upscale neighborhood on the northwest shore renamed for President Harry Truman who spent winters at his ‘Little White House’ on Front Street. Luxury mansions in the Italian and Greek Revival architectural styles and Southern Cottage-style homes line the beautifully manicured streets. Just outside the gate of the Annex is Fort Zachary Taylor State Park.
New Town (east of 1st Street and Flagler) is where most locals live, and there are great ways to enjoy the laid-back neighborhood. You’ll find Smathers Beach, Key West’s largest public beach, off S. Roosevelt Boulevard, as well as the Fort East Martello Museum. The Historic Charter Boat Row lies right on the edge of New Town, and boasts the largest fishing fleet in Key West. Rent out a charter for snorkeling, dolphin watching, or fishing, or walk along the pier and check out the ships. 24 North Hotel is also situated right in New Town!
The 16-block area southwest of Old Town is known for its Florida Conch architecture, good eats, and interesting history which began when the Bahamians and people of the Caribbean settled there in the 1800s. The neighborhood hosts The Bahama Village Goombay Festival each year during Fantasy Fest, which celebrates Caribbean culture with music, marching band parades, dancing, and jerk chicken. Bahama Village is also home to some of the most unique eateries on the island. Check out the free-roaming chickens and cats when you dine at Blue Heaven, make your own cocktail at Rams Head Southernmost DIY Bloody Mary bar, or enjoy great tapas and sangria at Santiago’s Bodega.
Midtown / White Street Gallery District
“The Local’s Duval” lies at the heart of the island, from White to First Street and North Roosevelt Boulevard to Flagler Avenue. Midtown is almost all residential, but the assortment of businesses, bookshops, restaurants, and art galleries, as well as the proximity to the beach, Duval Street, and New Town, make this neighborhood one of the most coveted destinations on the island.
Casa Marina District
This exclusive residential district just south of Old Town was once considered the “country side” of the island. The mid-century modern homes and Mediterranean mansions give the Casa Marina District its charm, while its waterfront restaurants, gardens, and parks make for an excellent place to relax overlooking the Atlantic Ocean.
Nestled in between Old Town and New Town on Key West’s northern shore, is the small residential area known as The Meadows. The wide, tree-lined streets of the neighborhood are a great place for a stroll, and bordering avenues like White Street, Truman Avenue, and Eisenhower Drive have some top-notch restaurants, art galleries, bakeries, and shops.
Planning a stay in Key West? Check out rates at 24 North Hotel. We have an on-site Starbucks, shuttle service to Old Town every hour, and our pool area is one of the best on the island. See our special offers - including special rates for Florida residents!