9 Best Hotels in the Florida Keys We Absolutely Love

This Middle Keys mainstay, one of the best hotels in the Florida Keys, has hosted the likes of Bing Crosby and Paul Newman—and outlasted the ravages of hurricanes and fire—to celebrate its 70th anniversary this year. The accommodations, however, are anything but dated: West Indies-inspired décor (think dark mahogany furniture, paddle ceiling fans, and tropical art) warm the 214 guest rooms, each with its own balcony and soaking tub, while the property’s Nikai Sushi Bar & Restaurant serves creative takes on sushi. Traveling with little ones? Send them off to Camp Cheeca for the day before taking a spin in the adults-only lap pool.

A seven-minute boat ride from downtown brings you to this gorgeous island hideaway, where 39 pastel-hued cottages dot a lush, 27-acre landscape. Swap the Key West party scene for customized spa treatments, a serene palm-shaded shoreline, and outstanding grouper tacos at the waterfront Latitudes Restaurant.

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It's just over the bridge from Florida's mainland, but this chic new property feels worlds away. The ten private bungalows and 144 breezy guest rooms done up in wood-paneled walls and deep blue area rugs surround a beachfront pool, just steps from the turquoise waters of Florida Bay. Dine at one of four onsite restaurants (our favorite: La Marea steakhouse for its sizable cuts and signature sauces like key lime béarnaise), then cozy up around a beachside fire pit to watch the sun sink into the Gulf.

You could days just relaxing on this oceanside sanctuary’s private beach, but the scene indoors is every bit as lovely. The recently renovated common areas and seafood-centric Oltremare Ristorante are decorated with vibrant tropical colors, while all 110 rooms feature cool earth tones, rattan chairs, and sweeping Atlantic views. Don't miss the hotel's Sparrows Rum Bar, which is known for fresh fish tacos and a killer key lime pie.

A recent $43 million renovation restored this beachfront grand dame—designed by the same architects behind the New York Public Library and the Met Opera House—to its original 1920s-era splendor (just look to the grand wooden columns and beams). There's no shortage of diversions on the property, from a 1,200 square foot beach (and the opportunity to jet ski, sail, or kayak) and two pools, to the decadent spa, with everything from aromatherapy to reflexology on offer. And did we mention the 6,500-square foot, 18-hole golf course on site?

Solitude reigns at this all-suite resort, originally built as a private estate in 1936. The former coconut plantation now houses 18 colonial-style cottages, whose open layouts, private verandas, and rustic accents (whitewashed walls, wicker furniture, colorful shutters) embody an authentic "Old Florida" look typically absent at most mega-resorts. There isn't much here to entertain—save for swimming off the property's pier and the intimate spa for basic treatments—but Cheeca Lodge is right next door.

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You'll find hints of South Beach all over this new 245-room property, from its contemporary, whitewashed design to the buzzy pool scene at the Rum Row bar. Other touches we love: the seascape photography by local artist and gallery owner Jorge de la Torriente, the custom platform beds and walls made with hand-washed pine, and an on-property cigar lounge and garden.

Live out your castaway fantasy at this romantic retreat, located halfway between Marathon and Key West and accessible only by seaplane or boat. Guests hop aboard the resort's yacht to reach the five-and-a-half-acre private island, where thatched-roof bungalows, mosquito net-canopied king beds, and a strict no-phone/no-television policy ensure you'll end your vacay completely recharged.

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A block off Duval Street and a short walk from the beach, this all-suite resort provides a hip haven in close proximity to Key West's downtown action. Each of the 35 modern two-bedroom suites features a full kitchen, private patio or balcony, and luxe perks like ice cream at check-in, complimentary poolside smoothies, and a daily wine happy hour.