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The southernmost of the Florida Keys, Key West is famous for its laid-back, booze-forward mentality. Each year, the spot draws thousands of visitors to its bars and restaurants (many of which you’ll find along Duval Street), its historic sights (like Ernest Hemingway’s house) and its gorgeous water views. There are breathtaking beaches, too, even though they’re not the main attraction here. Those looking to indulge in Key West’s charms will find there are dozens of hotels to choose from. Whether you're looking for a quaint cottage inn or a full-blown resort, you've got options.
Best Overall: Pier House Resort & Spa
When it comes to Key West hotels, there are a few things to pay close mind to, namely: location, amenities and water views. Not to spoil things for you, but the Pier House Resort & Spa has them all. It sits right in Old Town at the end of Duval Street, so guests are within easy walking distance of all the action, but it’s just removed enough that it can feel like a retreat from the party-hardy atmosphere. It’s also right on the waterfront, too, with a small private beach for guests to use. Rooms are relatively simple—decorated in a neutral palette with wood furniture—but that’s perfectly all right since guests spend most of their time elsewhere. If you're not out and about exploring Key West, there are plenty of things to do onsite, like pay a visit to the full-service spa and outdoor pool and hot tub, or grab dinner at one of three dining options. The hotel boasts one of Key West’s oldest bars, the Chart Room, where Jimmy Buffett once played.
Best Budget: Not Your Average Hotel
Key West isn't a cheap city and it's easy to splurge on a hotel. But if you want to save money, there are also plenty of budget options so you don't break the bank. One of the best is Not Your Average Hotel, or NYAH, which falls somewhere between a hotel and a hostel. You can book a bed in a shared room to save money, but the hotel also lets you add in extra beds to a private room without extra fees, perfect for groups of friends traveling together who don't want to pay for multiple rooms. Included with your stay are WiFi, continental breakfast every morning, and Starbucks coffee, helping to save money all around. And even though it's a budget option, NYAH is adults-only, so you can enjoy the pool, jacuzzi, and other facilities without having to worry about kids being around.
Best Boutique: The Gates Hotel
This former motel has been transformed into one of the best boutique hotels in Key West. Like many of its competitors, the hotel has a beachy aesthetic, but what sets The Gates apart is its dedication to top-notch modern decor, like wood-tile floors, wood-accented walls, and wood headboards (can you sense a theme here?). It’s all tastefully designed, though, and each room feels like a contemporary abode with patterned throw pillows, 48-inch HD TVs, mini-fridges, coffeemakers , and large desks. While the hotel isn’t quite within walking distance of the main action in Old Key West—it’s on the New Key West side of town—guests can enjoy fresh seafood from The Blind Pig food truck which parks its wheels poolside.
Best for Families: Santa Maria Suites
When traveling with a family, it’s usually best to book a hotel that gives you space, and the Santa Maria Suites does just that. Here, each suite with modern beach-decor offers two bedrooms, two bathrooms, a full kitchen, and in-unit laundry. The hotel feels like a luxe, quiet oasis, but it’s actually just a block away from Duval Street and the ocean. One of the best perks for guests is all the deals on food and drinks. There’s a daily happy hour for adults, while the kids can enjoy crackers, cheese, and chips along with smoothies and ice cream bars at the pool bar all day long.
Best Romance: The Saint Hotel Key West, Autograph Collection
One of Marriott’s Autograph Collection hotels, this 36-room boutique spot caters to a trendy crowd, particularly couples looking for a good time. We’d argue that it leans toward the edgier side of the spectrum, with sexy, sleek decor that includes whitewashed wood paneling and tufted headboards (not to mention peek-a-boo showers). Plus, the hotel’s motto—“play naughty, sleep saintly”—speaks for itself. The pool area is one of the gems here and though it’s small, it’s well designed with lush landscaping and a number of daybeds. Massages can be arranged here or in your room, too. There’s also the on-site fusion restaurant, Tempt, an intimate spot that dazzles with a whole lot of warm woods and red lighting.
Best Luxury: Casa Marina Key West, A Waldorf Astoria Resort
Built during Key West's 1920s building boom, this historic hotel stands proud as the grande dame of the island and you can feel it as soon as you step into its elegant wood-beamed lobby. Rooms don’t have the boldest designs, as they’re outfitted with minimalist wood furniture and beige is the predominant color. There’s also no formal fine-dining restaurant on-site, but guests can try the dishes at the poolside Sun Sun, which does serve upscale meals for a pool bar. The real draw of the hotel is its gorgeously landscaped grounds which encompasses two oceanfront pools and the largest private beach in Key West and one that is actually swimmable.
Best Nightlife: La Concha Hotel & Spa
Since opening in 1926, the landmark La Concha hotel on Duval has enjoyed hosting its fair share of famous guests, including Ernest Hemingway, Tennessee Williams, and former U.S. president Harry Truman. Since their visits, the hotel has been modernized quite a bit, though. La Concha's new sleek vibe is courtesy of dark woods and a palette of navy and brown, something that sets it apart from many of Key West's beachier-feeling hotels. At six stories, it’s the tallest building in town, and it capitalizes on its rooftop space with a serene spa that has suites with private guest balconies. Spa-goers are also welcome to order beverages and tapas after their service. For other entertainment, there’s a pool and tiki bar on the second-floor deck, a lobby restaurant, a wine bar, and a shop. The real nightlife draw at La Concha isn’t the hotel itself, but its prime location on Duval Street, meaning all the bars and restaurants are within walking (or stumbling) distance.
Best Business: The Marker Waterfront Resort
Most people aren’t in Key West on business, but for those who are, the Marker is an excellent place to stay. While it’s a five- to ten-minute walk to Old Key West’s restaurants and attractions, it sits just far enough away that you’ll be able to focus on your work (if you absolutely must). That said, the scene is quite fun here, with two pools in the central courtyard plus a bar that does tequila tastings and an adults-only spot that’s more secluded and reserved. When it's time for dinner, an onsite restaurant serves up California-style cuisine.
Best Oceanfront: Southernmost Beach Resort
Even though Key West is an island, a large number of its hotels are located inland. The Southernmost Beach Resort, however, has a six-acre property with stellar ocean views, particularly from its lounge-lined pier. It has a private beach—another rarity—and even a beachfront restaurant serving classic bar bites and seafood. With such expansive grounds, there’s space for 124 rooms spread between four different buildings. Each has its own vibe from more homey and vintage to relatively nondescript, so you might want to pay close attention when booking. There are also plenty of outdoor sports to enjoy here like croquet, bocce, and beach volleyball. Though if outdoor activity isn't your thing, you can always relax at the spa.
Best Gay-Friendly: Alexander's Guesthouse
Key West is famous for being an LGBTQ+ destination, and there's no shortage of gay-friendly hotels. While many of them cater exclusively to gay men, Alexander's truly welcomes everyone on the LGBTQ+ spectrum—including straight allies. Instead of the nightclub atmosphere and clothing-optional parties at other gay-friendly hotels, Alexander's Guesthouse is more of a tranquil oasis (although nude sunbathing is still allowed for tanning au naturel). And since the hotel is limited to guests over the age of 21, everything is focused on adults. It's also just a 15-minute walk to get to the most popular gay bars on Duval Street, so when you do feel like partying, it isn't very far away.
Best Adults-Only: Angelina Guest House
No hotel is more "adults-only" than one that is housed in a building that was once a clandestine gambling den and brothel during the Prohibition era. Even the guestrooms are named after famous working girls. But don’t worry, the property's seedy days are long gone and today guests are welcomed into a sweet, residential-feeling inn. While there’s no restaurant on-site, there is an outdoor pool and patio area with a hammock that transforms into a social area. There’s also a complimentary breakfast with some absolutely delicious cinnamon rolls. Even though it's adults-only, the focus is on tranquility and relaxation rather than partying. Even in the rooms, you won't find telephones or TVs, so you can fully disconnect and focus on your vacation.
Best Cottage: Sunset Key Cottages
Cottages are one of the quintessential accommodation options for staying in Key West, and those offered by Sunset Key Cottages are some of the most luxurious. Options range from one-bedroom cottages in the gardens to four-bedroom homes with oceanfront views, so you can enjoy a romantic trip with your partner or a whole group getaway with friends. The cottages are located on an exclusive island just 500 yards off the coast of Key West, so you can feel like you're in a tropical retreat but with all of the nightlife in Key West just a seven-minute boat ride away (transportation is complimentary for Sunset Key guests). If you want to splurge on the best way to stay in Key West, then the Sunset Key Cottages are definitely in the running.