15 Best Hotels in The Florida Keys, Florida

Haute tropicale best describes this wildly luxurious private-island retreat, and "second mortgage" might explain how some can afford the extravagant prices, but for those who can, it's worth the price. This property sits on a private 5½-acre palm-fringed island inhabited by Key deer, 3 miles offshore from Little Torch Key. The 15 oceanfront thatch-roofed bungalows house 30 suites with copper soaking tubs, mosquito-netting-draped king-size beds, and British colonial–style furnishings. Other comforts include an indoor and outdoor shower, private veranda, separate living room, and comfy robes and slippers. Two Island Grand Suites are twice the size of the others and offer his-and-hers bathrooms, an outdoor copper tub, and uncompromising ocean views. To preserve the quiet atmosphere, there are no TVs in the bungalows, and cell phones are highly discouraged in public areas.

This 12-acre, adults-only hideaway has charming freestanding bungalows (some of which are waterfront) that are outfitted with a front porch with Adirondack chairs, a sitting area with a couch, and a private patio with an outdoor soaking tub, shower, and seating area. Each bungalow comes with two bikes, and there are yoga classes, paddleboards, an outdoor exercise hut equipped with a Peloton bike, and boats and floating tiki cruises available for hire from the resort's waterfront. This being an all-inclusive resort means all meals and drinks are included, with the option to dine at three sit-down restaurants: Fish Tales, Bogie & Bacall’s, and Sea Señor. There's also a cozy "living room" and swanky cocktail bar Hemingway's inspired by the author's home in Key West.

One of the most storied and luxurious resorts in the Keys, this legendary property still packs in more amenities than any other we can think of. In the main lodge, sand-and-sea-inspired rooms boast luxurious touches like elegant outdoor soaking tubs that fill in a stream from the ceiling. The main building also holds three oceanfront restaurants including a sushi bar, two outdoor swimming pools, and two tiki bars to keep the party going. The resort's other buildings hold more styles of accommodations and a spa with a bevy of signature treatments, including hot-lava shell massages, as well as an adults-only lap pool with a bar, and a fitness center. In addition, 10 stand-alone "casitas" offer an ultra-private experience, with each one featuring furnished porches, fully equipped kitchens, and personal butlers. For the outdoorsy types, there's a 1,100-foot private beach, kayaks, bikes, fishing rods (to fish off the 525-foot pier), a walking trail, 9 holes of golf (designed by Jack Nicklaus), tennis, and water sports galore. For families, Camp Cheeca is the ideal place to drop off your kids ages 5 to 12; you get alone time, and they get a fun and educational program. Like shopping? The resort's signature store is open every day. At night, tiki torches light up paths and add even more ambience, if that's possible. 

Built in 1875, this gloriously shaded property was a labor of love from the get-go, and it covers a third of a city block in Old Town. Winding brick pathways lead past rare orchids, ponytail palms, black bamboo, fountains, a gazebo, and earthenware jars (called tinajones) imported from Cuba, each of which weighs a ton. Stone ostriches stand guard, close to the live tortoises. The romantic inn offers several types of accommodations, from standard rooms with garden and courtyard views to a two-bedroom carriage-house suite. Decorated with Bahamian plantation-style furnishings, the quiet and elegant rooms are a luxurious tropical retreat. All have private verandas. The wine bar draws locals and guests, as does free jazz on Sunday. What's more, its sister property, The Garden Cottages, immediately adjacent to the hotel, offers several luxurious apartments with full kitchens. A lagoon pool adds to the serenity.

This full resort—relatively rare in Key West—has large, tropical-look rooms and excellent on-site amenities, including a pool and bar overlooking Sunset Pier and a Thai-inspired spa. Toast the day's end at the waterfront bar or from the private balconies that extend from the stylish and homey rooms. High ceilings, hand-painted furnishings, wooden chests, and lavish whirlpool tubs create a personally designed look. The spa is small and without locker rooms, but it's the best in Key West, and three (of six) treatment rooms come with a Japanese-style tub on the balcony. The second floor's elegant restaurant is cleverly named Hot Tin Roof, a reference to its construction as well as to Tennessee Williams's Key West connection.

It's odd to call this a hidden gem when it sits on a prominent corner just one block off Duval, but a concrete facade keeps this luxurious find well secluded from the outside world. Six two-story buildings completely surround the courtyard filled with towering date palms and free-form swimming pools. And the suites offer as much inside as the courtyard does outside. Hello, gorgeous. Modern, spacious, with a touch of tropical verve and an overload of high-end style, the units have a chef's kitchen with a Jenn-Air cooktop, Cuisinart pans, and stainless fridge and freezer drawers (filled with ice-cream bars). Bathrooms are sleek with dual shower heads and vessel sinks. The long list of extras includes in-unit washer and dryer, umbrellas, toiletries, free poolside smoothies, a daily happy hour, and a nightly delivery of muffins. There's beach-chair setup at nearby South Beach, too.

This luxurious private island retreat with its own sandy beach feels completely cut off from the world, yet you're just minutes away from the action: a 10-minute ride from Mallory Square on the 24-hour free ferry. On idyllic, 27-acre Sunset Key you'll find swaying palms, flowering gardens, and a delicious sense of privacy. The comforts are first-class at the cluster of one- to four-bedroom cottages at the water's edge, some with garden or ocean views. Baked goods, freshly squeezed juice, fresh fruit, and a newspaper are delivered each morning. Each of the accommodations has a kitchen, and the resort offers a grocery shopping service (for a fee, of course). The spacious four-bedroom cottages also feature private plunge pools and washers/dryers.

Ralph Lauren could have designed the rooms at this stylish, luxurious resort on a nice beach. The 87 two- and three-bedroom town houses have gingerbread trim, white-picket fences, and open-floor-plan interiors decorated in trendy cottage style. The picture-perfect theme continues with the palm-fringed pool and the sandy beach edged with a ribbon of blue bay (and echoed in the blue-and-white stripes of the poolside umbrellas). Guests look like models on a photo shoot: attractive young families enjoying themselves on the sunny decks, or at the casual outdoor bar and elegant restaurant. Small, single-level guest rooms are ideal for couples looking to save money.

Geared specifically toward gay men, this hotel features a health club, a video lounge, a café and bar, and rooms in historic digs. Clothing is optional everywhere but in the gym.

This hotel attracts convention business by offering the biggest ballroom in Key West, but it also appeals to families with its spacious, impeccably and tastefully decorated rooms and one-, two-, or three-bedroom condo units. Designer furnishings reflect the resort's waterfront location. Real china in the kitchens and marble hot tubs add touches of luxury in the suites. Some rooms have spiral staircases down to the gardens and up to the rooftop sun decks. Families enjoy the beach and pool area. Adults enjoy the pool bar and fine on-site dining. Complimentary shuttles take guests to Old Town and the airport.

Behind 10-foot, dark-wood Kong gates is a Bali-inspired world, where tranquility washes over you like a rain shower. The entire property is spa-like with lush palms, buttonwoods, and orchids everywhere. The bungalows have a king bed in one room and a queen in the other, along with European fixtures, separate baths, and a small kitchenette stocked with water bottles. Relax in the large infinity pool, at the beach, or on the deck. Snorkel in the private lagoon, or just catch a magical Key Largo sunset. If you want even more space and privacy, rent the 5,000-square-foot Grand Lodge that sleeps eight.

These two-story, state-of-the-art, 1,600-square-foot villas could easily be the set for a Coastal Living magazine shoot. Interiors are white with lots of natural light, and each of the three bedrooms has its own spacious bathroom. You'll feel right at home with a gourmet kitchen, smart TV, audio system, keyless entry, and washer and dryer. There is even dock space for a small boat. Take advantage of the location and explore the numerous shops, restaurants, museums, and historic sites—all within walking distance.

At this tropical retreat, the embodiment of the laid-back Keys, hammocks sway between towering trees and aqua-green waves lap manicured sand. West Indies–style cottages with cypress and Dade County pine accents, colorful shutters, and private verandas sit in a canopy of coconut palms and lush landscaping on a residential street off the highway. This is a high-end slice of Old Florida, so don't expect tacky tiki bars and music; do expect the sound of rustling palms and ospreys chirping. The one-, two-, and three-bedroom cottages all have modern kitchens with modern appliances. During busy season, there may be a one-week minimum. The Moorings has the same high standards as neighboring Cheeca Lodge but is less cramped, more private and exclusive, and possibly the most beautiful property in the Keys.

This waterfront resort's two three-story, Keys-style buildings huddle around its 37-slip marina in the middle of Old Town overlooking Mallory Square. Formerly the Margaritaville resort, it was revamped in 2021 by the Opal Collection, which gave the 178 guest rooms and suites a refresh with lots of natural light, rich woods, a neutral color palette, and private balconies. Most of the rooms, which are large by Key West standards, look out on the Gulf of Mexico, but you might end up looking at a cruise ship for your entire visit.

This upscale resort, near Mallory Square in the heart of Old Town, offers a wide range of amenities, including a beach and comfortable, traditionally furnished rooms. The location—on a quiet stretch of shore at the foot of Duval—is ideal as a buffer from and gateway to the action. Its sprawling complex of weathered gray buildings includes an original Conch house. The courtyard is a riot of tall coconut palms and hibiscus blossoms, and rooms are cozy and colorful, with a water, pool, or garden view. Six top-of-the-line suites extend over the water with sunset views. Rooms nearest the public areas can be noisy.