The string of islands that make up the Florida Keys are connected by the Overseas Highway, with its more than 40 bridges taking you across 113 miles of land and green-blue sea. Many visitors head straight to Key West, located at the end of the road, to sip key lime coladas poolside during the day and join the party on bar-lined Duval Street at night.
But if you have the time, a leisurely drive down the highway with overnights at a few hotels is the perfect way to experience the laid-back, retro vibe the Florida Keys offer. Here are some of the best places to stay along the way.
Baker’s Cay Resort in Key Largo — Photo courtesy of Baker’s Cay
Key Largo is known for diving and snorkeling, so you’ll definitely want to get out on the water (or under the water, in the John Pennekamp Coral Reef State Park underwater preserve). Back on land, beaches in the Florida Keys are manmade and small, but there’s plenty of room to stretch out on a lounger at Baker’s Cay Resort, part of Hilton’s Curio Collection.
The hotel is set up motel-style, with outside walkways leading to the spacious, modern rooms, many with balconies overlooking the Florida Bay. Step outside to the beach and calm waters, complete with anchored rafts for sunbathing and a beach bar slinging icy pina coladas.
A winding path leads to what feels like a secret beach, with scattered chairs tucked under trees at the water’s edge. The resort also includes an indoor/outdoor Mexican restaurant, a more upscale Caribbean-Creole restaurant and two pools separated by a waterfall.
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Next is Islamorada (say it: eye-la-morada), an understated collection of keys known for fishing, with a long history of famous visitors arriving to cast their reels. The grounds that now make up Cheeca Lodge & Spa in Islamorada have been welcoming visitors since the 1940s – according to the hotel, Harry Truman was an early guest; other politicians and celebrities later followed suit.
Cheeca has been rebuilt and renovated more than once, and it’s now a tropical-chic, unpretentious property with endless options for things to do. Sign up for water sports, tennis, golf, beach volleyball, kayaking, fishing and more, or settle in at a cabana next to one of the pools. Don’t skip a stroll out on the 525-foot wooden fishing pier.
While you’re in the area, make sure to get to the brightly painted Islamorada Brewery & Distillery for a cocktail with purple hibiscus gin or a flight of easy-drinking beers – the No Wake Zone Coconut Key Lime ale is especially quaffable.
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With only eight cottages set on a former coconut plantation, Moorings Village has a more intimate feel than many of the bigger Keys resorts (the hotel used to be a bit bigger itself, but sold some of its cottages to nearby Cheeca). The cottages have one to three bedrooms, with full kitchens and verandas perfect for sipping your morning coffee and enjoying the quiet.
Hammocks, lounge chairs and hundreds of palm trees on this beachfront property insist that you unwind. If you do need to work off some energy, there’s a pool, a tennis court and kayaks and paddle boards. Moorings Village doesn’t have any restaurants onsite, but there are plenty nearby. Don your nicest sundress for a seafood dinner at Chef Michael’s, just a few minutes up the road.
Angler & Ale restaurant at Hawks Cay in the Florida Keys — Photo courtesy of Hawks Cay Resort
Halfway between Key Largo and Key West is Hawks Cay on Duck Key, a great option if you’re traveling with kids (it was even named a USA TODAY 10Best Readers’ Choice Awards winner for Best Family Resort in 2020). This family-friendly resort set over 60 acres along the Atlantic Ocean is a destination unto itself, with six restaurants and bars, a saltwater lagoon, a spa, a marina and five pools, including one with a pirate ship theme.
Every type of water activity you can think of is available, like snorkeling, kayaking and fishing. There’s also a long list of options geared toward kids and teens – including drop-off programs for when you’re craving an adults-only afternoon. All of the guest rooms come with balconies. If you’re traveling with friends or extra family, two-bedroom suites and villas are available, too.
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In Marathon, book a morning tour at the non-profit Turtle Hospital to meet rescued 300-pound loggerheads and other sea turtles, followed by lunch at a nearby Cuban cafe (try Paradise Cuban Restaurant). Then check into Tranquility Bay, which lives up to its name with curved rows of airy white townhouses in a serene beachfront setting.
Spacious two-story accommodations face the water, with some leading out to the sand and some set on a secluded lagoon. If you’re looking for a more typical hotel room, those are tucked among greenery next to one of the two pools. The elegant Butterfly Cafe in the main building is a good option for dinner.
Isla Bella Beach Resort in Marathon, Florida — Photo courtesy of Rachel Vigoda
You’ll feel like you’re approaching a secluded country estate as you drive the winding tree-lined road to Isla Bella. White buildings and blue accents give this Marathon hotel a Mediterranean look that feels far from Florida.
Sip champagne while you check in, then drop your bags in the room and head to the spa or one of the five pools – the lagoon-shaped main pool has a bar serving tropical drinks. The guest rooms have crisp, clean decor and oversized bathrooms. Each includes a balcony facing the ocean or, if you’re on the ground floor, a porch that leads out onto the sand.
The view from a guest room balcony at The Perry Hotel — Photo courtesy of Rachel Vigoda
After driving over the iconic Seven Mile Bridge and detouring to Bahia Honda State Park for a photo op from the old rail bridge, disembark at the Stock Island Marina for a stay at The Perry Hotel. With its lightly nautical theme, water views and top-notch service, The Perry is a perfect compromise between the quieter keys and party-central Key West.
A free shuttle ride takes you to and from downtown Key West, though there are places to eat both onsite at the hotel and nearby if you’d rather spend the day at one of The Perry’s pools and then stay local for dinner. Make sure to take an early morning stroll out on the piers to check out the boats. If you’re extra lucky, you might even spot a manatee swimming near the farthest dock.
Winslow’s Bungalows, a Kimpton hotel in Key West — Photo courtesy of Kimpton
Surrounded by palm trees and greenery, the retro-styled Winslow’s Bungalows is one of five Kimpton properties in Key West, each a revamp of an existing boutique hotel. The Bungalows’ beachy white clapboard buildings dating back to the 1800s and early 1900s feel like old Key West, with small but comfortable rooms and a peaceful setting.
It’s still an easy walk to the action, whether you’re looking for a daytime dolphin-watching tour (go with Honest Eco) or a lively evening out. There are pools and an open-air bar where the bartender is ready with frozen shots – or book an absinthe tasting at the similarly styled Kimpton Lighthouse Hotel with local distiller Key West Trading Company for a very mellow afternoon.
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The sprawling Southernmost Beach Resort is set on the quieter end of Duval Street, not far from a monument marking the southernmost point of the continental U.S., just 90 miles from Cuba. The resort, which was originally separate hotels, is now an all-in-one tropical escape with multiple eateries, pools and beaches, a spa, a pier lined with loungers and a range of room types set across low-rise buildings.
If you can, book an oceanfront king room – the water views from the balcony are worth it. After a day poolside, stretch your legs with a 25-minute stroll up Duval to Mallory Square, where crowds gather nightly to watch the sun sink into the ocean. To end your Florida Keys road trip in style, take the ferry to Sunset Key for dinner at Latitudes, set right on the beach (book well in advance).
About Rachel Vigoda
Rachel Vigoda is the author of travel guidebook Moon Pennsylvania from Hachette Book Group. She writes about food, travel, and culture for Eater, USA Today, Philadelphia magazine, and other publications and always has a restaurant recommendation ready. Favorite trips (so far): Galapagos Islands, Indonesia’s Gili Islands, and Israel.