Schooner Spirit of Independence

Upscale lodging offering modern rooms with free Wi-Fi, plus 3 outdoor pools & a restaurant. A 9-minute walk from Mallory Square, this upscale, waterfront hotel is 2.5 miles from Smathers Beach. Airy, modern rooms offer private balconies, free Wi-Fi and flat-screen TVs, plus minibars and Keurig coffeemakers. Some provide pool or harbor views. A resort fee includes access to an exercise room and 3 outdoor pools. A relaxed restaurant serves a fusion of Californian and Mexican fare, and there’s a poolside bar. Bike rentals are available.

Pizzeria specializing in New York-style slices, plus salads, sandwiches & gelato.

Guesthouse with low-key rooms & detached conch houses, plus a heated pool & a daily happy hour. This relaxed, art deco-style guesthouse in historic Old Town dates from 1924, and is a mile from The Ernest Hemingway Home and Museum, and a 9-minute walk from Duval Street’s restaurants and bars. Decorated in soft hues, the main guesthouse offers both rooms with en suite bathrooms and rooms with shared facilities. Some provide private porches, and all have free Wi-Fi. Some rooms include flat-screen TVs, microwaves and minifridges. There are also several restored conch houses on the property with rental units, and some have full kitchens. There's a daily complimentary happy hour. Additional amenities include a heated outdoor pool and a hot tub.

Discover a charming Key West gem for sponges and souvenirs, where friendly staff ensure you leave with treasures and good vibes—just bring your patience for the heat!

Upscale resort on the beach offering seafood dining, a spa & an outdoor pool, plus free Wi-Fi. Overlooking the Gulf of Mexico, this upscale waterfront resort is a 5-minute walk from Mallory Square and a mile from the Southernmost point buoy. All the chic, contemporary rooms have balconies and feature flat-screen TVs, iPod docks and pillow-top mattresses, plus minifridges and free Wi-Fi. Upgraded rooms add gulf views and/or additional sitting areas. Amenities include beach access, a heated outdoor pool and a hot tub with a sundeck, and a spa, plus a fitness center, a seafood eatery and a bar. Jet ski rentals and breakfast are available, and there's a business center. Parking is extra.

Longtime open-air hangout for seafood complemented by live music & dockside views.

A lively Key West pub with a charming outdoor patio, serving hearty bar fare and featuring upbeat live music that keeps the good vibes flowing.

Nestled on the Gulf of Mexico, this tropical retreat boasts lush landscaping, four inviting pools, welcoming staff, and cozy rooms with garden or water views.

Cozy, romantic spot serving French-Caribbean fare, signature hog snapper & a broad wine list.

Airy, laid-back rooms & cottages in a hotel offering free Wi-Fi & breakfast, plus an outdoor pool. Set in a gated compound with 5 buildings, 1 of which was built in 1930, this quaint upscale hotel is a block from the shops and restaurants on Duval Street, and a 5-minute walk from the Ernest Hemingway Home and Museum. Airy, relaxed rooms with private bathrooms offer flat-screen TVs, free Wi-Fi and minifridges. Upgraded rooms add en suite bathrooms, coffeemakers and sitting areas, plus patios or porches. Cottages with 1 or 2 bedrooms sleep up to 4 people and have kitchenettes. Complimentary continental breakfast is served by the heated outdoor pool. There's also a shaded courtyard with seating.