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

| Courtesy of Oceans Edge Resort and Marina / Expedia
James Callery

Home to world-class diving and fishing, southern Florida is blessed with a diverse selection of places to stay in Key West. There are beachfront retreats aplenty, but if you’re looking for something a little different, why not stay in an Ernest Hemingway favorite? Or perhaps a nautically themed boutique property where you can dock your boat? Whatever you have in mind for your Florida Keys vacation, you’re sure to find your bliss from among this handpicked selection of the best hotels in Key West, all bookable with Culture Trip.

1. Casa Marina Key West, A Waldorf Astoria Resort, for 1920s allure

Resort, Hotel

Luxe-retro king room with crisp linens, white tile floors and sliding doors to patio at Casa Marina Key West
Courtesy of Casa Marina Key West / Expedia.com

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.

2. Oceans Edge Resort and Marina, for saltwater swimming

Resort

A bright and refined living room space with retro style, wall art and prime waterfront views at Oceans Edge, Key West
Courtesy of Oceans Edge Resort and Marina / Expedia

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.

3. The Perry Hotel, for contemporary Florida cool

Chain Hotel

Cavernous lobby space with exposed concrete pillars, wood floors and long couches at Perry Hotel in Key West
Courtesy of the Perry Hotel / Expedia

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.

4. NYAH, for a unique concept hotel

Budget Hotel, Chain Hotel

View from above of pools and deck areas at NYAH in Key West
Courtesy of NYAH / Expedia

NYAH – Not Your Average Hotel – offers a build-your-own-room concept, with the hotel customizing rooms to fit your group size. In other words, no one has to take an uncomfortable fold-out bed. With everyone enjoying a good night’s sleep, the day starts off right, improved with a complimentary continental breakfast. Spend your time cooling off in the three pools or relaxing in the hot tub. It’s also a short walk to the vibrant Duval Street. If you’d like to explore further afield, the adults-only resort offers bike rentals.

5. 24 North Hotel, for aquatic adventures

Budget Hotel, Independent Hotel, Hotel

Comfy king room with sofa, artwork and views of the water at 24 North Hotel in Key West
Courtesy of 24 North Hotel / Expedia

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.

6. The Gates Hotel Key West, for poolside lounging

Independent Hotel

A beachy modern guest room with light woods at the Gates Hotel Key West
Courtesy of the Gates Hotel Key West / Expedia

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.

7. The Saint Hotel Key West, Autograph Collection, for happy hours

Boutique Hotel, Hotel

A blue-and-white toned guest room with two beds and polished wood floors at the Saint Hotel Key West
Courtesy of the Saint Hotel Key West, Autograph Collection / Expedia

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.

8. Parrot Key Hotel and Villas, for relaxing and unwinding

Independent Hotel

The tropical luxe pool area at Parrot Key Hotel and Villas in Key West
Courtesy of Parrot Key Hotel and Villas / Expedia

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.

9. Eden House, for a chalet feel

Boutique Hotel

Cozy guest room with large bed, sofa, wooden walls and ceilings and tile floors at Eden House in Key West
Courtesy of Eden House / Expedia

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.

10. Margaritaville Beach House Key West, for an adventure-seeker's hideaway

Resort, Hotel, Luxury

Large multiform pool and lounge chairs set amid palm trees at Margaritaville Beach House in Key West
Courtesy of Margaritaville Beach House Key West / Expedia

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.

Fancy staying at a plush resort in Key West? Check out our pick of the best resorts to book in Key West, Florida, and book your stay with Culture Trip.

Suzy Pope contributed additional reporting to this article.

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