The Best Hotels to Book in the Florida Keys

Soak up spectacular sunset views at these top properties in the Florida Keys
Soak up spectacular sunset views at these top properties in the Florida Keys | Courtesy of Ocean Key Resort - A Noble House Resort / Expedia.com
Joe Bindloss

There aren’t too many more scenic places in the US than the Florida Keys. 120 islands make up the archipelago, which is a fabulous destination for fishing, snorkeling and everything in between – so book your hotel with Culture Trip and test out your sea legs.

The one-time haunt of Hemingway, the favored winter retreat of President Truman and the setting for Humphrey Bogart and Lauren Bacall’s final film, the Florida Keys have long been celebrated as the glamorous end of the Sunshine State. Here, there are hotels in vintage mansions and glam retreats on yacht-crammed marinas, plus any number of lavish beachside resorts. Just pick your island, order a rum punch and settle in on the terrace to watch the sunset.

1. Tranquility Bay Beachfront Hotel and Resort

Hotel, Resort

Balcony with Adirondack chairs and view of white sands at Tranquility Bay Beachfront Hotel and Resort, Marathon Key, Florida
Courtesy of Tranquility Bay Beachfront Hotel and Resort / Expedia

A gleaming white statement on a white-sand beach, close to where the Seven Mile Bridge enters Marathon, Tranquility Bay delivers the Florida Keys you’ve always imagined. White wooden verandas look out over the sea from the two-story beach houses, palm fronds dance in the breeze and garden rooms offer glimpses of green through Venetian blinds. Full-sized kitchens with giant fridge-freezers elevate the beach houses into sophisticated self-catering spaces.

2. The Gardens Hotel

Boutique Hotel, Bed and Breakfast

The Gardens Hotel
Courtesy of The Gardens Hotel / Expedia.com

Palm fronds tickle the frontage of this gorgeous Key West mansion, which could have been plucked from a black-and-white movie. Whirring fans circle gently overhead on the terrace and balcony, and rooms spill from the main building into cottages in the grounds. Handsome antique writing desks, four-poster beds, cane armchairs and eclectic works by Key West artists give the rooms an old-time feel, conjuring the atmosphere of the island’s heyday.

4. Orchid Key Inn

Hotel

Orchid Key Inn
Courtesy of Orchid Key Inn / Expedia.com
A vintage charmer in downtown Key West, Orchid Key Inn fits its name – orchids erupt in the courtyard garden, which surrounds an alluring geometric pool, and rooms are decorated in a bright, summery palette that brings the colors of the beach, sea and town into the living spaces. It’s an understated oasis in a handy location for the historic center, the shoreline and Fort Zachary Taylor, at the very end of the Keys.

5. The Perry Hotel & Marina Key West

Chain Hotel

Large bright luxury bedroom with large outdoor balcony overlooking the marina at the Perry Hotel and Marina Key West
Courtesy of the Perry Hotel and Marina Key West / Expedia.com

It’s all about the sea at this stand-out-from-the-crowd hotel that brings a bit of industrial chic to the Florida Keys. Take a drink out onto the terrace and balconies, and the views conjure dive trips, fair winds and deep-sea fishing. Looking in the other direction, it’s all about exposed timber, steel angles and smooth concrete. Rooms have acres of glass to let in the views, along with clean white lines, lush linen and warm-toned woods.

6. The Saint Hotel Key West, Autograph Collection

Boutique Hotel, Hotel

The Saint Hotel Key West, Autograph Collection
Courtesy of The Saint Hotel Key West, Autograph Collection / Expedia.com

Walk about 300ft (91m) from this low-key but luxurious Key West hotel and you’ve gone as far west as you can go in the Florida Keys without tumbling into the sea. Set inside a classic, weatherboard-fronted Key West house, the Saint is small and intimate, with a tucked-away garden pool, and high-style rooms with mirrored furniture, iHome digital sound systems, crisp linen and ocean-blue ceilings. There’s a restaurant and bar, and more great dining in the grid of streets right outside.

7. The Grand Guesthouse

Hotel, Guesthouse

The Grand Guesthouse
Courtesy of The Grand Guesthouse / Expedia.com

Two blocks south from the historic Key West cemetery, the Grand is as unpretentious and easygoing a stay as you’ll find anywhere in the Florida Keys. Behind gently nodding palms and an airy veranda, you’ll find cute, cozy rooms with colorful bits of art and their own private entrances, set around a shady, tropical yard. The house has a classic Key West story – it was built as dormitories for cigar-rollers during the 1880s. On-site parking is an extra plus.

8. Ocean Key Resort and Spa

Resort, Spa Hotel

Ocean Key Resort - A Noble House Resort
Courtesy of Ocean Key Resort – A Noble House Resort / Expedia.com

The Ocean Key serves up the full tropical package, slotting seamlessly into its Key West setting. Smart, summery rooms with day-beds on the veranda look directly onto a vivid sweep of turquoise blue, with passing yachts for company. Colorful wooden chairs and tables, shaded by sun umbrellas, fill the hotel’s private jetty, and huge windows bring the swish of the Gulf of Mexico into the room as you sleep.

9. Amsterdam's Curry Mansion Inn

Hotel

Amsterdams Curry Mansion Inn
Courtesy of Amsterdam's Curry Mansion Inn / Expedia.com
A lavish wedding cake of a mansion in the old town in Key West, Amsterdam’s has instant star quality. Behind the historic facade, with its dormers, wooden shutters and whitewashed balustrades, rooms have an easy Key West feel, with carved, curved canopy beds, timber floors and patchwork bed-covers. The name comes from the villa’s original owner, William Curry – Florida’s first self-made millionaire. Sip a long drink on the curving veranda and you’ll be transported back a century.
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