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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 it’s gorgeous water views. There are 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 inn or a full-blown resort, you've got options. Read on for some of the Floridian city's best.
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: Angelina Guest House
There’s no need to splurge on accommodations in Key West as a number of great hotels fall into the budget category. One of the absolute best is the Angelina Guest House, which calls a 1920s-era gambling den and brothel home. But don’t worry, the property's seedy days are long gone (though rooms are named after famous working girls), and today, guests are welcomed into a sweet, residential-feeling inn. While there’s no restaurant onsite, 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. Guests should note that this is an adults-only property, and most rooms don’t have phones or TVs, meaning you’ll likely be able to find peace and quiet here.
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 offers two bedrooms, two bathrooms, a full kitchen and in-unit laundry, and each is well-appointed with modern, beach-chic decor. 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 freebies; there’s a daily happy hour for adults —though kids can enjoy crackers, cheese and chips — and smoothies and ice cream bars are free 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.
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 grand 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 — they’re outfitted with minimalist wood furniture and beige is the predominant color. There’s also no formal fine-dining restaurant onsite, but guests can try the dishes at the poolside Sun Sun, which does serve upscale meals. The real draw of the hotel is its gorgeously landscaped grounds which encompasses two oceanfront pools and the largest private beach in Key West —one that is actually swimmable.
Best Nightlife: La Concha
Since opening in 1926, the landmark La Concha hotel on Duval has enjoyed hosting its fair share of famous guests, including — among others — 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 and a wine bar and shop. The real nightlife draw at La Concha isn’t the hotel itself, but its prime location on Duval, 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.