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
Photo of Joe Bindloss
29 September 2021

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.

Tranquility Bay Beachfront Hotel and Resort

Hotel, Resort
4.5/5 (975 Reviews)
Tranquility Bay Beachfront Hotel and Resort
Courtesy of Tranquility Bay Beachfront Hotel and Resort / Expedia.com
Price Drop
Now from $426 per night
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.
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The Gardens Hotel

Boutique Hotel, Bed and Breakfast
4.8/5 (727 Reviews)
The Gardens Hotel
Courtesy of The Gardens Hotel / Expedia.com
Price Drop
Now from $503 per night
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.
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Coconut Palm Inn

Hotel
4.7/5 (402 Reviews)
Coconut Palm Inn
Courtesy of Coconut Palm Inn / Expedia.com
Price Drop
Now from $312 per night
Occupying prime grounds in Tavernier on Key Largo, the Coconut Palm Inn has been welcoming guests to the Keys since 1947, with a broad waterfront frontage facing a stretch of blue water and the hotel’s boardwalk jetty. Airy rooms with period flourishes have terraces enveloped by a lush tropical garden, and the expansive suites face onto the hotel’s palm-dotted beach. All have little details which recall the building’s history, such as Audubon Society bird prints – a nod to the original owners’ favorite hobby.
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Orchid Key Inn

Hotel
4.8/5 (980 Reviews)
Orchid Key Inn
Courtesy of Orchid Key Inn / Expedia.com
Price Drop
Now from $370 per night
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.
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  • The Perry Hotel & Marina Key West

    Chain Hotel
    4.6/5 (969 Reviews)
    The Perry Hotel & Marina Key West
    Courtesy of The Perry Hotel and Marina Key West / Expedia.com
    Price Drop
    Now from $303 per night
    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.
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    The Saint Hotel Key West, Autograph Collection

    Boutique Hotel, Hotel
    4.5/5 (953 Reviews)
    The Saint Hotel Key West, Autograph Collection
    Courtesy of The Saint Hotel Key West, Autograph Collection / Expedia.com
    Price Drop
    Now from $161 per night
    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.
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    The Grand Guesthouse

    Hotel, Guesthouse
    4.7/5 (542 Reviews)
    The Grand Guesthouse
    Courtesy of The Grand Guesthouse / Expedia.com
    Price Drop
    Now from $298 per night
    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.
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    Ocean Key Resort and Spa

    Resort, Spa Hotel
    3.7/5 (698 Reviews)
    Ocean Key Resort - A Noble House Resort
    Courtesy of Ocean Key Resort – A Noble House Resort / Expedia.com
    Price Drop
    Now from $87 per night
    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.
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    These recommendations were updated on September 29, 2021 to keep your travel plans fresh. This article is an updated version of a story created by Joe Bindloss

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