Last Updated on April 16, 2021 by Katrina

Photo credit: Pier House Resort & Spa

With its quirky-island personality, Key West offers one of the quintessential Florida experiences. About 168 miles from Miami, the island is the tip of the Florida Keys. It holds plenty of cultural and pop-culture history, thanks to the lore of Ernest Hemingway, Tennessee Williams, Jimmy Buffet and more. But it also offers a vibrant present-tense culture. That’s largely due to fun-loving bars and the nightly entertainment during the sunset at Mallory Square. No doubt, experiencing the best of this laidback island ambience sometimes comes at a premium. But these five places to stay offer an abundance of both amenities and charm. Here are the best hotels in Key West.

Pier House Resort & Spa (1 Duval St.; 305-296-4600) Duval Street

This 142-room, six-building resort is a classic, thanks to its shutter-style aesthetics and serious place in Key West history. Jimmy Buffet played his first gig here, Bob Marley once played here, and Truman Capote wintered here. “The luxury resort maintains an authentic Old Key West attitude with help from local art and the Chart Room Bar, which continues to serve free popcorn and steers clear of any neon slushie drinks,” says Travel+Leisure. “Some rooms are a bit dated in their decor—there’s still a surprising amount of rattan here,” says Condé Nast Traveler. “But suites have patios or balconies, making them ideal for enjoying a Key West sunset.”

Ocean Key Resort & Spa (0 Duval St.; 305-809-8072) Mallory Square

This contemporary waterfront resort is super-close to the harbor, Duval Street, and Mallory Square. And the hotel offers its own great sunset view from the aptly named Sunset Pier restaurant. “Each of the boutique hotel’s 100 rooms has a private balcony overlooking either historic Duval Street or the ocean,” says Travel+Leisure, “letting guests be a part of the action on their own terms.” One Tripadvisor user says the Ocean Key is “a beautiful hotel in a perfect location, and staff is awesome.” But consider asking for a room away from the bustling restaurant if you want quiet.

Sunset Key Cottages (245 Front St., 305-292-5300) Sunset Key

Accessible only by boat, this 27-acre key right off Key West is comprised of 32 Victorian-style cottages with full kitchens, big verandas, and a private beach. “All nestled in jasmine-scented gardens and surrounded by unbroken water views, the residences are as picturesque as they are grounded in convenience,” says Timeout. Cottages have up to four bedrooms and all come with one big perk. You’ll get pastries and fruit delivered to your porch each morning. “You feel like you’re on your own private island,” says one Google user.

Southernmost Beach Resort (508 South St., 800-354-4455) Southernmost Point

The name alone tells you where to find this lush six-acre resort on Key West. But it doesn’t express how chill the place feels. South of most of the action on Duval Street,” says Condé Nast Traveler, and “it’s a great option for sanctuary-seeking couples or families with kids.” One Google reviewer points out the mix of Victorian and Colonial buildings offers distinctly different experiences: “Half the hotel is the quality of motel while other half is nicer style hotel.” Still, Southern Living calls the resort “sweet serenity … kick back in one of the oceanfront hammocks.” Tip: Consider renting a golf cart for exploring beyond the resort.

Hyatt Centric Key West Resort & Spa (601 Front St.; 305-809-1234) Mallory Square

Located between Mallory Square and the Southernmost Point buoy, this 120-room branch of the big brand offers easy access to the big sights, but also conventional resort perks. “The resort is quite large, with a man-made beach, pool, restaurants and bars,” says one Google reviewer. “You can really sit back and relax here, with a beautiful view of the Gulf.” One Tripadvisor user liked that “the hotel has all the amenities my family was looking for—on-site Jet Ski rental, electric car or golf cart rental for exploring the town, great pool, marina with multiple private boating options, and great restaurants.”

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