Home to world-class diving and fishing, the island city of Key West, Florida, is blessed with a diverse selection of hotels. There are beachfront retreats aplenty, but if you’re looking for something a little different, why not stay in an Ernest Hemmingway favorite? Or perhaps a nautically themed boutique property where you can dock your boat?
Oceans Edge Resort and Marina
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.
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.
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.
This luxury hotel on lively Duval Street opened in 1926 and was a favorite of Tennessee Williams (who finished A Streetcar Named Desire here) and Ernest Hemmingway. Today, it has an alluring outdoor pool served by a poolside bar. You can also unwind at the hotel’s rooftop spa and slip into the evening with a visit to Wine-O, the hotel’s trendy wine bar that features an extensive selection of bottles, along with cheese and charcuterie nibbles.
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 its waterproof books, or head to the Cuban-inspired craft cocktail bar, Republica Bar & Lounge.
Right on the beach, Ibis Bay carries a distinct Cuban influence with its vibrant decor and swaying hammocks. That continues into the brilliantly tropical rooms, which feature bright hues and floral motifs. Throughout your stay, keep an eye out for the unusual wildlife that also calls the area home; iguanas, macaws and tortoises are among the creatures you might spy. Also, join the daily shark feed, which takes place at the dock.
You can almost smell the salty air from your light and airy room thanks to the hotel’s Keys-side 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. However, the infinity 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 spot 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 wooden 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 sundeck 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. Here, you’re encouraged to raid the on-site Gear Garage for activity inspiration, with sea kayaking and fishing among the more tantalizing choices. 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.
With three pools surrounded by tropical gardens and an Old Town Key West setting close to the action, the Marquesa Hotel finds a sweet spot between luxury accommodation and somewhere that feels like a home. Its cafe comes highly rated, serving up grilled meats and fresh seafood to excite foodies from the hotel and beyond, and if you feel like heading out after a few glasses of wine, the bars on Duval Street are only a short walk away.
These recommendations were updated on December 15, 2020 to keep your travel plans fresh.