4 Star Hotels in Key West

New Town gives you a quieter slice of Key West living away from the tourist crowds. This peaceful residential area offers wide streets for strolling and a glimpse into authentic island life. Nearby Smathers Beach and the Key West Tropical Forest provide natural escapes when you need a break from the bustle. Budget-friendly chain hotels and vacation rentals make this area wallet-friendly for longer stays. Cuban-American eateries and family restaurants offer affordable meals, while shopping plazas with grocery stores help you feel right at home. A car is handy, but free parking is plentiful throughout the neighborhood.

The Key West Historic District lets your inner wanderer loose on pastel-painted streets steeped in salty charm. Ernest Hemingway's old stomping grounds mix with lively bars and the nightly sunset celebration at Mallory Square. History buffs explore the Truman Little White House while party people hit Duval Street for live music and tropical drinks. Fresh seafood and Cuban-influenced cuisine fuel your adventures between historic Victorian B&Bs and boutique inns with tropical courtyards. Getting around is easy—just stroll the narrow brick streets, hop on a narrated trolley tour, or rent a bike to cruise this flat, compact island paradise.

Downtown Key West dazzles with its historic charm and non-stop energy. Wander Duval Street's lively scene, visit Hemingway's famous six-toed cat sanctuary, or catch the sunset celebration at Mallory Square where fire-breathers and musicians perform against stunning Gulf backdrops. The neighborhood's Victorian mansions with gingerbread trim and weathered coral stone churches create a unique tropical atmosphere. The area serves up fresh seafood from casual waterfront joints to upscale restaurants. Most attractions sit within a walkable six-block radius, though you can hop on the Conch Tour Train when your feet need a break. Boutique hotels and historic inns with tropical courtyards offer charming places to crash after experiencing the legendary bar scene.

Truman Annex delivers presidential history with a side of peaceful luxury just steps from Key West's action. Tour the Harry S. Truman Little White House where tropical gardens frame the preserved presidential retreat. Stroll past gleaming naval buildings on manicured grounds or explore maritime treasures at the Mel Fisher Museum. The quiet, tree-lined streets feel worlds away from Duval Street's energy. Elegant vacation rentals occupy restored naval quarters with premium amenities and tropical courtyards. Getting around is best done on foot or by bike through the gated community's uncrowded pathways. When hunger strikes, a short walk takes you to nearby Old Town's restaurants and shops.