Hotels tree outdoor leisure swimming pool Resort property estate vacation Pool Villa condominium palm caribbean home mansion backyard hacienda palace arecales plant Deck area surrounded
Hotels

9 Best Hotels in the Florida Keys We Absolutely Love

Paradise is closer than you think: the 110-mile ribbon of highway linking Florida’s famed archipelago has postcard-perfect beaches and endless ocean views, with stylish hotels to match. Sarah L. Stewart takes us on a tour of the 9 best hotels in the Florida Keys.

Hotels Island Lodge Lounge Patio Pool Trip Ideas Tropical tree outdoor table leisure chair swimming pool Resort estate Villa caribbean Deck swimming several
1

Cheeca Lodge & Spa, Islamorada

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.

Check Prices for Cheeca Lodge & Spa in Islamorada, FL

Hotels tree outdoor building house property home estate condominium real estate residential area Villa plant Resort facade cottage mansion residential apartment Courtyard bushes Garden
2

Sunset Key Cottages, Key West

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.

RELATED: America's Dreamiest Islands

Check Prices for Sunset Key Cottages in Key West, FL

Hotels indoor wall floor room Living property ceiling living room condominium Suite real estate estate home interior design furniture apartment cottage
3

Playa Largo Resort & Spa, Key Largo

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.

Check Prices for Playa Largo Resort & Spa, Autograph Collection in Key Largo, FL

Beach Beachfront Hotels Resort Romance Scenic views water tree outdoor sky palm plant Ocean body of water palm family vacation Sea arecales morning sunlight woody plant Sunset Coast tropics sandy lined Lake shade shore
4

Amara Cay Resort, Islamorada

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.

Check Prices for Amara Cay Resort in Islamorada, FL

Hip Hotels Living Lounge Luxury Modern floor window indoor room building furniture living room interior design hardwood window covering home Bedroom wood flooring real estate bed
5

Casa Marina, Key West

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?

Check Prices for Casa Marina, A Waldorf Astoria Resort in Key West, FL

Beachfront Hotels Luxury Resort tree outdoor grass house building home cottage estate red yard backyard shack Garden lush
6

The Moorings Village & Spa, Islamorada

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.

RELATED: Coolest Beach Hotels in the USA

Check Prices for The Moorings Village in Islamorada, FL

Florida Hotels tree sky outdoor swimming pool building property estate Resort condominium leisure mansion home vacation reflecting pool Villa resort town palace real estate surrounded
7

The Gates Hotel, Key West

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.

Check Prices for The Gates Hotel Key West in Key West, FL

Beach Beachfront Bedroom Hotels Island Resort Romance Romantic Scenic views Waterfront indoor curtain bed room property interior design cottage home Suite estate Villa living room real estate farmhouse furniture decorated
8

Little Palm Island Resort & Spa, Little Torch Key

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.

RELATED: 12 Swoon-worthy Overwater Bungalows

Check Prices for Little Palm Island Resort & Spa – A Noble House Resort in Little Torch Key, FL

Hotels Kitchen Modern indoor floor room property ceiling estate home real estate interior design counter condominium Design appliance apartment Suite cottage stainless steel Island area
9

Santa Maria Suites, Key West

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.

Check Prices for Santa Maria Suites in Key West, FL

Want more?