The Best Hotels to Book in Key West, Florida, for Every Traveler

A palm-lined driveway leads to the entrance of this former retreat for Hollywood’s elite. Perhaps this is the last bastion of Key West’s 1920s allure – the architectural features of the era still shine through in colonnaded walkways, sweeping staircases and timber-beamed ceilings. Perched on the edge of the Old Town, Casa Marina has a private beachfront, lined with lounge chairs and cabanas, and there are two shimmering oceanfront pools to choose from. If you want something a little more active, water sports vendors line the private beach, offering deep-sea fishing, sunset cruises, jet-skiing and bicycle rental, too.

True to its name, Oceans Edge enjoys a plum spot on the shores of the Atlantic Ocean. This bright, neat and refined resort overlooking the marina comes with six heated saltwater pools, and if you’d like a bit more action, you can charter a boat or borrow the complimentary bicycles, kayaks or stand-up paddleboards. When it’s time for grub, head to Yellowfin Bar & Kitchen for Caribbean-tinged dishes. At one point during your stay, hop on the resort’s free shuttle service to explore downtown Key West.

Named after Commodore Matthew C. Perry, a celebrated modernizer of the United States Navy, the Perry Hotel is suitably marine-focused with a 288-slip marina and two waterfront pools surrounded by palms. Diving and fishing spots are also plentiful in the area. When you’re not splashing around, hop on a shuttle bus to explore the Old Town before soaking up evening entertainment at the hotel’s event lawn and stage, which has a packed schedule. Rooms at this pet-friendly hotel feature in-room refrigerators and oversize private balconies.

With its sparkling white façade with baby blue accents and grand fishing mural overlooking the pool, 24 North Hotel screams tropical fun. The theme continues in the bedrooms, with most having pool or ocean views, and when it’s time to venture out, speak to the concierge to arrange an aquatic adventure. How about deep-sea fishing or a seaplane tour? For something a little more chilled, take advantage of the hotel’s underwater library and waterproof books, or head to the Cuban-inspired craft cocktail bar, Republica Bar & Lounge.

You can almost smell the salty air from your light and airy room thanks to the hotel’s waterfront location. Its pool is one of those difficult to move from – the perfect spot for soaking up some sun. If you get hungry, swing by the Blind Pig food truck, where you’ll be served tasty tapas and dishes influenced by Key West’s varied communities. After that, perhaps a drink will be in order. The hotel’s partnership with a local rum distillery means you’ll be kicking back Caribbean-style.

The motto of the Saint Hotel Key West is “play naughty and sleep saintly.” The hotel certainly provides ample opportunity for both. It’s only a short walk from the bar-lined Duval Street, and with relaxing lounge music playing by the pool, it’s perfect for nursing a hangover. That being said, the pool also comes with a butler, where you can order cocktails at your leisure. With a three-hour happy hour each day and the music getting livelier in the evening, the temptation to let your hair down once more might just prove irresistible.

Surrounded by lush palm trees, the white-painted wooden buildings of this downtown Key West property greet you like a warm hug. Rooms are nice and bright, and the lure of four swimming pools is sure to lead to some blissed-out afternoons. Enjoy ocean views from a hammock or under the shade of a parasol. If your energy levels have picked up, hop on the free shuttle bus to the Old Town so that you can tour the museums and do a bit of shopping.

Old meets new at this Art Deco hotel, now almost a century old and run by Mike Eden since the mid-’70s. The rooms have a modern aesthetic, and some come with wood floors and ceilings, bringing a quirky feel that almost resembles a ski lodge. Poke your head out the door, and you’ll be reminded once more of your setting, where tropical plants and spaces to bask in the heat abound. Try the elevated deck or the heated pool, or if you feel up to exploring the area, take advantage of the on-site bike rentals.

A short walk from the palm-lined Smathers Beach, this resort takes inspiration from Key West’s (unfortunate) history of shipwrecks. The resort itself is a beacon of good taste, and whether it’s lounging under a poolside cabana or playing games on the lawn, you won’t struggle to find ways to unwind here.