Where to Stay in Key West: Old Town Historic Inns vs Historic Seaport & New Town

Key West is divided down the middle along White Street into two distinct hotel worlds: historic, walkable Old Town on the western half of the island, and modern, car-friendly New Town on the eastern half near the airport and Smathers Beach.

1. Quiet Residential Streets of Old Town (Fleming, Eaton & Simonton)

If you want to step out of your garden gate under bougainvillea and walk to Duval Street, the Hemingway Home, Mallory Square and dozens of restaurants in 5 to 10 minutes without needing a car, stay one to three blocks off Duval for peaceful nights away from bar music. Key West is famous for restored 1880s Victorian mansions turned into boutique inns around tropical lagoon pools, such as Mermaid & The Alligator, Artist House, Lighthouse Court opposite Hemingway's house, Marquesa Hotel with its three pools and Café Marquesa, and The Gardens Hotel.

2. The Historic Seaport & Mallory Square Waterfront

Ideal if you want full-service waterfront resorts with piers, sunset views and instant access to snorkel and sailing boats, led by Ocean Key Resort & Spa (0 Duval Street), Pier House Resort & Spa (with a private Gulf beach), Opal Key Resort & Marina and The Marker Key West Harbor Resort.

3. Southernmost / South Beach (Atlantic End of Duval Street)

Stay on the Atlantic shore for oceanfront pools and beach access at Southernmost Beach Resort, historic 1920 Casa Marina Key West and The Reach.

4. New Town (East Key West) & Stock Island (Best for Car Drivers & Families)

Because Old Town hotel rooms are compact and charge steep nightly parking fees, staying 3 miles east in New Town (North Roosevelt Boulevard or Smathers Beach), or on Stock Island, gets you spacious modern rooms with resort pools (at Margaritaville Beach House, The Capitana, Laureates Key West, or marina-front The Perry Hotel on Stock Island), and most run an hourly shuttle van to Old Town.