With its love for happy hour and sprawling beaches, the Florida Keys is perhaps the best embodiment of rest and relaxation in the United States. Each hotel that graces the chain of islands feels like it’s been designed to ensure that travelers’ expectations of a restorative vacation are met. I grew up in the Florida Keys, and was lucky enough to explore many of the hotels in the area, where I spent afternoons swimming in pools, enjoying amenities, and befriending the staff. As an adult, I’ve returned to many of my old haunts and found that all their charms still hold true—and I’ve noticed a few new gems pop up on the scene, too. Here are the eight best hotels in the Florida Keys.

Top Places to Stay
Hawks Cay Resort

The pool area at Hawks Cay Resort.

Hawks Cay Resort

Also available to book at Expedia.com

Rates: $$
Location: Marathon
Nearby Attractions: Curry Hammock State Park, Sunset Bay Park on Grassy Key, Dolphin Research Center
Standout Amenities: Five swimming pools, saltwater lagoon, full-service spa

Voted one of the best resorts in Florida in 2025 by Travel + Leisure readers, Hawks Cay Resort sits directly in the middle of the chain of islands, making it a great base to explore the entirety of the Keys. Because of its location on Duck Key, the resort feels a bit more low-key and exclusive than its neighbors in Key Largo or Key West. If you’re vacationing with a large group, there are a variety of villas to choose from with an optional upgrade to a space with a private pool. There are also five different areas to swim in, including a private saltwater lagoon where you can paddleboard or kayak, which, in my opinion, is the best way to explore the Keys.

Cheeca Lodge & Spa

A guest room in Cheeca Lodge.

Cheeca Lodge

Also available to book at Expedia.com

Rates: $$Location: IslamoradaNearby Attractions: Green Turtle Hammock Nature Preserve, Keys History & Discovery Center, Morada Way Arts & Cultural DistrictStandout Amenities: 27 acres of grounds, 2 open-air Tiki bars, 1,200 feet of private white sand beach

With roots dating back to 1947, this 27-acre ocean resort has a sort of Islamorada magic that makes you want to stay forever, including a golf course, lush gardens, exquisite pools, and a soothing spa. The atmosphere here feels quite luxurious, but the hotel is still very family-friendly, and has a kids’ pool plus Camp Cheeca, which provides daily activities for the kiddos so you can enjoy your vacation, too.

Islander

The Islander Resort pool and cabanas.

Islander Resort

Also available to book at Expedia.com

Rates: $$$Location: IslamoradaNearby Attractions: Keys History & Discovery Center, Green Turtle Hammock Nature Preserve, Morada Way Arts & Cultural DistrictStandout Amenities: Private beach access, multiple sports courts, two hot tubs and two swimming pools

Islander is another Islamorada staple. The resort has rooms on both the bayside and the oceanside, allowing you to choose whether you prefer watching the sunrise or sunset from your room. Travelers have no shortage of activities to choose from, whether it’s bocce on the sand, volleyball on the beach, or sauntering across the street to the famous Lorelei’s historic Green Turtle—you can’t go wrong with any decision you make at the hotel. Islander is also home to the Florida Keys History & Discovery Center, a perfect excursion for kids or the history aficionado in your life.

Ombi

Wide view of a private bungalow in the middle of the water.

Burlap & Blossom LLC/Ombi

Also available to book at Expedia.com

Rates: $$$Location: Key LargoNearby Attractions: None—Ombi is located off the shore of Key LargoStandout Amenities: Ocean views in every room, kayaks and paddleboards, hot breakfast and dinner delivery available upon request

Ombi is an out-of-this-world stay. Located off Key Largo, Florida, these three floating bungalows provide an intimate, private experience with stunning ocean views—perfect for couples. After a five-minute boat ride, you’ll arrive at your overwater bungalow. Once aboard, you can unwind in a hammock, relax on the deck, or explore the waterways with a kayak or paddleboard. Although breakfast and dinner are available upon request, keep in mind that this hotel is removed from the mainland, so you’ll need to bring your snacks and food if you don’t opt for a delivery.

The Gardens Hotel

Exterior of The Gardens Hotel.

The Gardens Hotel

Also available to book at Expedia.com

Rates: $$Location: Key WestNearby Attractions: Key West Lighthouse, The Hemingway Home and Museum, Keeper’s Quarters Museum
Standout Amenities: Private room entrances, heated outdoor pool, every room has either a verandah, balcony, or deck

As you could probably gather from the name, The Gardens Hotel is a plant lover’s dream. With roots dating back to the 1800s, the property was purchased in 1930 by founder Peggy Mills, who aspired to turn it into a botanical garden. Mills soon earned herself the title of “The Lady of the Orchids,” and you’ll be able to spot rare Hawaiian and Japanese orchids that she collected, still thriving here. In addition to gorgeous grounds, guests will be able to enjoy fine vintages on site at the D’vine Wine Gallery—interestingly, D’vine is self-serve. If you’re a jazz lover, be sure to plan your trip around a Sunday evening so you can enjoy live jazz in the gardens from 5 p.m. to 8 p.m.

Marquesa

Courtesy of The Marquesa

Also available to book at Expedia.com

Rates: $$Location: Key WestNearby Attractions: Fort Zachary Taylor Historic State Park Beach, Southernmost Point of the Continental U.S.A., Higgs Beach
Standout Amenities: Three swimming pools, gorgeous tropical gardens, concierge services

Marquesa may be one of the most unique properties in the Sunshine State. Constructed in 1884, the main building of the hotel was originally a butcher’s home and still retains tons of Old Florida charm. You can frolic through the courtyard, enjoying the comforts of Southern charm, while surrounded by French-Gothic architecture that is painted with the bright colors of Florida. After your stroll through the surrounding historic neighborhood, head out into town, as you’re within walking distance of Old Key West. Even better, rent a golf cart and ride around town in true Floridian style. This boutique property’s legendary status isn’t just all talk, either—in 2024, it earned two Michelin Keys.

Simonton Court Historic Inn & Cottages

Exterior of Simonton Court.

Simonton Court

Also available to book at Expedia.com

Rates: $Location: Key WestNearby Attractions: Audubon House & Tropical Gardens, The Studios of Key West, Nancy Forrester’s Secret Garden
Standout Amenities: Poolside continental breakfast, welcome hour craft time, four swimming pools

What once was a cigar factory has since been transformed into a quaint inn with just six cottages, perfect for couples looking to experience Old Key West. This adults-only property is located near the city’s most popular attractions, including Sloppy Joe’s and Mallory Square, making it an ideal home base for those who would prefer to explore on foot. Guests can enjoy the inn’s private gardens and one of its four relaxing pools, which were inspired by Hemingway’s nearby estate. Poolside service allows you to sip cocktails, and the pool is open 24/7.

Isla Bella Beach Resort

Beach lounge chairs at Isla Bella Beach Resort.

Nina Ruggiero/Travel + Leisure

Also available to book at Expedia.com

Rates: $$Location: MarathonNearby Attractions: 7 Mile Bridge – Vista Point, Turtle Hospital, Sombrero Beach
Standout Amenities: Oceanfront pools, fitness center, complimentary bike rentals

Isla Bella Beach Resort makes it easy for you. Every room has an oceanfront view, so each space gives you a front-row seat to Florida’s Magic. The property is located next to the world-renowned Seven Mile Bridge, one of the world’s longest segmental bridges, which connects Marathon and Pigeon Key. For those looking to get out on the water and enjoy a quintessential Keys experience, the resort provides fishing charter services out of the marina. Choose from backcountry fishing, reef fishing, offshore fishing, or swordfishing, and be prepared for the freshest seafood dinner of your life. If you don’t necessarily have your sea legs, the property encompasses an entire mile of waterfront, giving you plenty of space to find a private spot to relax.