The Best Resorts to Book in Key West, Florida

If you don’t associate Key West with the Roaring Twenties, one night at Casa Marina will change that. A former hideaway for the Old Hollywood elite, its sole mission is to make you feel like an A-lister from check-in to check-out. The largest private beach on the island is yours to enjoy – when you’re not lounging by one of the two outdoor pools or getting steamy in the spa, that is. Let your hosts help you plan a private dinner on the beach to reinforce just how much of a (holiday) celebrity you really are.

Set by the waters of the Key West Bight, Hyatt Centric Key West Resort and Spa is tantalizingly close to the bars yet untroubled by the bar-hopping crowd. This boutique hotel is not unlike the people who call Key West home – a little quirky and very laid-back. Your furnished private balcony is the best place to sneak a peek of the sunset – if you don’t have the energy to make it to Mallory Square. And if you need a getaway from your getaway for any reason, you can charter a boat with the snap of a finger from the hotel dock.

Ocean Key Resort and Spa not only enjoys spectacular views over the Gulf of Mexico, but it also has the coveted address of Zero Duval Street – the main drag downtown dotted with watering holes and places to eat. Too tired to head out? Epic views are served up in all three on-site restaurants, although it’s your choice if you want a white tablecloth catching your crumbs or a pair of swimming trunks. Our advice? Split the night into fine dining at Hot Tin Roof Restaurant, then slip into something more comfortable for cocktails on Sunset Pier.

Key West resort-style relaxation without the high prices comes with a cast-iron guarantee at the DoubleTree Resort. With the free airport shuttle, you can be slathering the sunscreen on during the ride so that when you arrive at the hotel, all you have to do is grab a warm cookie at check-in and drop off your luggage. The shuttle drops off in Old Town, too, where you can have adults-only or family-friendly fun around Duval Street. A low-key afternoon may be necessary; if so, the waterside bar and zero-entry pool are lounge-lizard spaces par excellence.

As you might have deduced from the name, resorts in Key West don’t get much closer to the Southernmost Point of the Continental US than the Southernmost Beach Resort on the Atlantic Coast. The private tanning pier ensures all-over bronzing – nothing short of a cloud will cover your nakedly ambitious pursuit of color. Spend time floating in one of the three heated pools, but keep an eye on your tan. The only bright-red encounters you want in Key West are a bloody mary and a lobster dinner.

Let the Marker Key West Harbor Resort show you what upscale local living is all about. It’s a harbourfront hotel, meaning fishing and boating action takes place practically outside your port-view suite. Mornings are made for indolence; have a lie-in, followed by coffee on the terrace and an afternoon devouring fish tacos and other light bites by the pool. A little light activity? Venture out on a rented bicycle, but head back to the Marker in good time for a Key West spritzer or Hemingway daiquiri by the pool.

Oceans Edge is the resort in Key West that you’ll pine for from the moment you leave – what else could explain the high returnee count? It has six swimming pools and a private marina set within 20 acres (8ha) of palm-tree-shaded paradise. Paddleboard fitness classes, morning yoga classes, movie nights and poolside games are all included in your room rate. The exclusive one-hour Eco Experience, led by a marine scientist, is the definite shortcut to meeting sea life, from sea lions to sharks. With so much on the schedule, you’ll hardly remember what your balcony suite looks like.