The Best Beach Hotels to Book in Key West, Florida

A stay at the six-acre (2.5ha) Southernmost Beach Resort is the perfect introduction to Key West. Allow us to count off the reasons why: four bars, three heated pools, two beaches and one private tanning pier that’ll ensure you go home with the perfect Florida glow. All suites are solid options, but why not enjoy your first visit in style by staying in the Dewey or La Mer House? These ocean-view abodes were former Victorian houses and can now be yours to call home for however long you wish to stay in paradise.

They say it’s always five o’clock somewhere – and if ever a place epitomized the sentiment, it’s Margaritaville Beach House on Key West. Even the standard rooms are highly covetable, in serene pale tones with either tropical-garden or lagoon-style-pool views. A suite with a full kitchen and dining area is convenient, but you’re not here to break a sweat cooking. The property’s Tip Cup Chalice Bar & Chill will whip up smoked fish dip, a backcountry fish sandwich and a super sweet piece of banana cream pie whenever you wish. Peruse the drinks menu, and before you know it your margarita will be on its way.

Yes, it’s a hotel. Beside the beach. In Key West. But a stay here is not exclusively about the sands. Not when there’s so much fun to be had messing about on the water. Speed away from the seven-acre (2.8ha) grounds on a jet-ski tour – or how about a boat chartered from the marina? Grab a paddleboard, and you can watch the sea glitter and fade to evening. A hotel shuttle will take you to Old Town if you’re missing the land, though the Beachside Express Water Taxi will keep you on the water longer.

With Cuba only 90mi (145km) south across the water from here, it’s no wonder the island’s lovely culture makes its presence felt on Key West – and Havana Cabana is one of the best places to experience the beauty of it. Settle in for views of postcard-Cuban vintage American cars, vibrant music and expertly stirred mojitos – what an escape from reality! Throw on your guayabera and fedora for a tour of Key West in one of the hotel’s ‘57 Chevys. End your weekend with Loteria games and churros on Sunday nights. All that’s missing is a fine Cuban cigar. But who’d want to smoke up the balcony of their elegant pool-view room anyway?

Book a premium pool or ocean view suite at the 24 North Hotel and you’re in for instant relaxation at this refurbed motel that’s so handy for Old Town. The aforementioned accommodation features dazzling granite countertops, stunning handpicked local photography and a wet bar where you can mix a perfect Key lime margarita. Need a change of scenery? Try craft cocktails at the in-house Republica Bar and Lounge. Scoff conch fritters at Toasted Coconut, the poolside restaurant. Or head out with a coffee – Starbucks caffeine hits are yours on the ground floor after yoga on site – complimentary every weekend.

You’ll feel like a castaway in the best possible way at Oceans Edge Resort. No foraging for nuts and berries here – instead, eat crispy calamari, guava-braised short ribs and blackened catch of the day. If you do fancy living just a little like Crusoe, bring in your fresh-caught fish and the chef will cook it up anyway you like with two sides and sauce. You’ve got six pools to choose between, as well as perfect relaxation time in whichever jaunty blue-and-white-colored room you pick. There’s even a private marina – float your boat?

Who in their right mind would stop a mere bridge away from Key West? If you do, the Perry Hotel will reward you with a glass of champagne at check-in. This celebratory drink is well deserved, as you’ve discovered a hotel on Stock Island that puts nearby Key West at your fingertips. It’s right on the marina, so you can hop on a shuttle to Old Town whenever you fancy throughout the day. You probably won’t want to leave the oversized balcony and waterfront views from your suite, though. In which case, settle in snugly, stepping out occasionally to eat bagels and buttermilk pancakes at the hotel’s Matt’s Stock Island Kitchen & Bar – one of three fine places to eat in-house.