Old Town walkability, waterfront resorts, quiet Atlantic blocks, and marina stays
Where to stay in Key West
The right Key West stay depends on what you want outside the room. Old Town puts evenings on foot; the Southernmost area softens the nightlife; New Town and Stock Island offer pools, parking, and space at the cost of central walkability.
Stay picks
Where To Stay
Havana Cabana at Key West
Havana Cabana leans into a playful Cuban-inspired resort atmosphere, with a large pool and an Old Town shuttle for travelers who do not need to stay directly on Duval Street.
Santa Maria Suites Resort
Santa Maria Suites places suite-style rooms and two pools near the quieter end of Duval Street, useful for travelers who want more space while staying within walking distance of Old Town sights.
Hampton Inn
Hampton Inn Key West pairs an oceanfront setting near the airport with a large pool and shuttle access, suiting travelers who prefer a quieter base outside Old Town.
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront offers a New Town waterfront base with a landscaped pool area, suited to travelers who value on-site parking and plan to drive or shuttle into Old Town.
Casa Marina Key West, Curio Collection by Hilton
Casa Marina is a historic oceanfront resort on Key West’s south shore, combining beach access and resort amenities with a location close enough for an easy walk or short ride into Old Town.
The Reach Key West, Curio Collection by Hilton
The Reach offers a polished south-shore resort stay with a private natural-sand beach and walkable access to the quieter end of Duval Street.
Old Town
Best for first-time walkability to Duval, Whitehead Street, the seaport, sunset, and dinner. Historic buildings may have stairs, compact rooms, and limited parking.
Southernmost and upper Duval
Quieter than the busiest blocks, close to the Atlantic edge and Southernmost Point, with a longer walk to Mallory Square and the seaport.
New Town waterfront
Larger resorts, pools, parking, and airport proximity can suit families or relaxation-focused trips, but dinner and Old Town usually require transport.
Stock Island
Marinas, modern hotels, and a working-waterfront mood sit east of Key West. Confirm shuttle frequency or plan on driving, biking, taxi, or rideshare.
Choose the location before the pool
A walkable room changes the whole evening
Old Town parking is scarce and heat changes the feel of even a short walk. Ask exactly where the room sits, whether parking is included, how many stairs are involved, and whether nightlife reaches the property. A resort farther east may deliver a better pool and quieter sleep, but add rides for nearly every historic-site dinner or sunset outing.