The Best Hotels in the Florida Keys

While some travelers speed along the Florida Keys Overseas Highway on their way to bustling Key West, others know that hidden along that spectacular stretch of road are resorts that understand laidback luxury and the profound pleasures of a day spent in a hammock under a palm tree or fishing on calm waters. These hotels, lodges, and beach resorts let you unplug from the rush of modern life while enjoying amenities and activities that will enrich your stay.

81801 Overseas Hwy, Islamorada, FL 33036, USA
Cheeca Lodge manages to be upscale and relaxed at the same time. This duality is perhaps best embodied in Cheeca’s flagship restaurant Atlantic’s Edge, which offers a refreshed take on island cuisine (like the roasted red snapper with dragon fruit or the hibiscus swordfish) in an elegant but breezy oceanfront setting. The 27-acre luxury resort on Islamorada Key—one of the sport-fishing capitals of the world—was renovated following damage from Hurricane Irma in 2017. The revamped lobby, fully rebuilt fishing pier, 214 redesigned guest rooms, and new Italian restaurant have made Cheeca even better than before. Airy suites feature curated artwork, hand-tufted rugs, and rattan accents, and each suite opens to a private lanai with a partially enclosed open-air jacuzzi. A new point of pride is the refreshed 5,700-square-foot spa, which now has seven treatment rooms, a wet room with Vichy shower, hydrotherapy facilities with a steam room, and a fully equipped fitness center. Still to come in early 2019 is a brand new oceanfront pool (bringing the resort’s total to three, including a saltwater lagoon) and tiki bar, 25 South. If you must leave, book a fishing excursion, sunset cruise, or round of golf at the 9-hole Jack Nicklaus-designed course—and enroll the kids in the eco-focused Camp Cheeca.
61 Hawks Cay Blvd, Duck Key, FL 33050, USA
You don’t have to go far to find fun at Hawks Cay, nor do you have to go far to relax by the water there. The resort, which takes up much of tiny Duck Key, is known for its lagoon, five pools (including one reserved for adults and another featuring a pirate ship slide), and a Dolphin Connection program that offers complimentary viewings and hands-on experiences. Water sports are plentiful as well, with kayaks, paddleboards, and boats to rent, and guests can book fishing trips, scuba and SNUBA diving, and kiteboarding instruction. There’s also a Cliff Drysdale tennis program, a spa and fitness center, and a kids club. The resort closed for one year after Hurricane Irma, reopening in September 2018 after a $50 million renovation to the main hotel, a project that included the redesign of all 177 rooms and suites, as well as the creation of a new upscale steakhouse, a seafood-focused café, and a marketplace with to-go options—these supplement the three poolside grills and cocktail bars. Privately owned two-and three-bedroom homes are also available to rent through the resort.
123 Beach Road, Islamorada, FL
Moorings Village has a setting out of an island fantasy, stretched along one of the largest private beaches in the Keys, with more than 1,000 coconut palms shading its 18 guest villas. After a direct hit from Hurricane Irma, the resort reopened in January 2018 with 100 newly planted coconut trees, a new picturesque dock, and a refurbished swimming pool—while still maintaining its eclectic design and luxurious feel. The individually styled villas—each with a wraparound veranda—have kitchens, living and dining spaces, and a selection of artwork collected during resort owner Hubert Baudoin’s travels. Ocean activities rule the day here (unless you’re lolling in a hammock) and the property offers complimentary kayaks, paddleboards, and bikes, in addition to coordinating excursions like scuba diving, kitesurfing, sailing, and fishing. And because the resort takes up both sides of the Key of Islamorada, guests can catch the sunrise and then witness sunset while dining at either Pierre’s (an upscale spot with French fusion cuisine) or the Beach Café (a casual bistro serving Caribbean-American food). Pro tip: Book your visit to coincide with the full moon to attend the Mooring’s monthly beach party for live music, fireworks, and bonfires on the beach.
136 Madeira Rd, Islamorada, FL 33036, USA
Casa Morada’s dressed-down modern coastal style reflects a love of the ocean, island plant life, and luxurious comforts. The 16-suite boutique hotel—once a 1950s roadside motel—underwent an extensive renovation in the early 2000s that transformed it into one of the Key’s sexiest spots. The Raymond Jungles–designed gardens are lush, the outdoors showers and jacuzzis are impossibly romantic, and the resort’s private island features a freshwater pool. If you can rouse yourself for anything other than relaxing by the water, try your hand at a game of bocce, snorkle around the only living coral reef in North America, go on a sunset sail, or charter a boat tour with local resident Captain Bill to visit the Mangrove Islands or Three Sisters Bird Rookery. Pro Tip: Morning yoga classes are offered every Wednesday, Saturday, and Sunday at 9, but guests can book a private session anytime.
97450 Overseas Hwy, Key Largo, FL 33037, USA
When it opened in 2016, Playa Largo, part of Marriott’s Autograph Collection, was Key Largo’s first new luxury hotel in 21 years, and its casual, sun-drenched luxury was a welcome addition to the mellow Upper Keys. The resort’s 177 rooms and suites offer a range of accommodations—most with great bay views. Upgrade to one of the ten bungalows for a private back porch surrounded by lush gardens and a second-level balcony. For ultimate privacy—and luxury—book the Beach House with three master bedrooms, wrap-around balconies, a private pool, event lawn, and private beach. The property’s four restaurants (the toes-in-the-sand Sand Bar is ideal for watching sunset), spa, fitness center, pool, and beach offer plenty of ways to relax, or partake in activities like snorkeling, diving, kayaking, paddleboarding, parasailing, fishing, sailing, or a glass-bottomed boat ride. Pro tip: Hobnob with the school of more than 100 tarpon that linger near the resort by hand-feeding them from the resort dock.
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