The Best Resorts to Book in Key West, Florida

The Casa Marina Key West has every amenity you could want, including two pools and a private beach
The Casa Marina Key West has every amenity you could want, including two pools and a private beach | Courtesy of Casa Marina Key West, a Waldorf Astoria Resort / Expedia
Photo of Nick Dauk
18 November 2021
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Resorts in Key West are very well versed in the art of relaxation. Whether they’re on a private beach or hiding in a palm-trimmed oasis, those resorts surrounding Old Town and New Town are so laid-back that everyone walks around in swimsuits day and night. Amazing views, delicious seafood and shuttles to the most popular sights on the island are all standard when you choose the best resorts Key West has to offer. Book now on Culture Trip.

Casa Marina Key West, a Waldorf Astoria Resort, for the star treatment

The Spanish-style facade of the Casa Marina Key West, with a wide walkway flanked by shrubs, palm trees and rectangular ponds
Courtesy of Casa Marina Key West, a Waldorf Astoria Resort / Expedia

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.

Hyatt Centric Key West Resort and Spa, for boutique-hotel comforts

The outdoor pool with lime-green loungers and umbrellas and water views at the Hyatt Centric Key West Resort and Spa
Courtesy of Hyatt Centric Key West Resort and Spa / Expedia

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, for epic dining options

The swanky outdoor pool with loungers the color of the sea and potted plants at the Ocean Key Resort and Spa
Courtesy of Ocean Key Resort and Spa / Expedia

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.

Pier House Resort and Spa, for 24-carat relaxation

The private white-sand beach with the Beach Bar at the Pier House Resort and Spa beside it
Courtesy of Pier House Resort and Spa / Expedia

Getting into the island state of mind is effortless when lounging on the white sands of the private beach at Pier House. This luxe resort at the head of Duval Street is exactly where you’ll want to start your day and end your night. After the bar shenanigans on Duval, sleep deeply and wake up refreshed in your ocean-view room. The warm Florida sun will be shining on your private balcony. How to spend your day? Beach, pool, dinner, bar and whirlpool tub. You won’t have to leave the property once.

DoubleTree Resort by Hilton Hotel Grand Key – Key West, for lounge-lizard lazing

Resort
The outdoor pool surrounded by loungers, greenery and pink cabanas at the DoubleTree Resort by Hilton Hotel Grand Key – Key West
Courtesy of DoubleTree Resort by Hilton Hotel Grand Key – Key West / Expedia

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.

Southernmost Beach Resort, for beautiful bronzing

Hotel balconies overlook an outdoor pool with loungers and water features at the Southernmost Beach Resort
Courtesy of Southernmost Beach Resort / Expedia

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.

The Marker Key West Harbor Resort, for Hemingway-worthy tipples

A spacious king room in soothing white and blue with a waterfront balcony at the Marker Key West Harbor Resort
Courtesy of The Marker Key West Harbor Resort / Expedia

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 Resort and Marina, for wildlife wonders

Oceans Edge Resort pool area with plush lounge chairs, blue umbrellas and row of palm trees in Key West, Florida
Courtesy of Oceans Edge Resort and Marina / Expedia

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.

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