The 9 Most Beautiful Florida Keys Resorts (2019)

Popular among many travelers, the islands that make up the Florida Keys are known for their natural beauty and charming, eccentric atmosphere. The coast is surrounded by mangrove forests, sandbars, and offshore reefs, while the main towns of Key West, Marathon, and Key Largo are home to everything from tiki huts to lively LGBTQ+ nightlife. Given the region’s popularity, there are plenty of resorts to choose from. Whether you’re traveling with the whole family, a group of friends, or a significant other, one of these nine beautiful resorts will provide the perfect backdrop for your Florida Keys vacation.

Cheeca Lodge & Spa, Islamorada

The expansive Cheeca Lodge & Spa enjoys a lengthy stretch of beachfront on Islamorada. With a nine-hole golf course, sea kayaks, tennis courts, two pools, and full-service spa, it provides the perfect balance for an active and relaxing vacation. To access these amenities, guests must travel along paths that wind through lush gardens and tropical foliage. The beach is strewn with lounge chairs between towering palm trees and a tiki bar serving cocktails and snacks. A private fishing pier extends more than 500 feet from the beach, where guests can get free fishing gear and experience unobstructed views of the Atlantic Ocean. Further ocean exploration can be had on chartered fishing trips and snorkeling excursions. Come evening, the wooden jetties on the interior lagoon area are lit up by tiki torches, creating a charming atmosphere for a drink before dinner. Cheeca Lodge operates three restaurants in addition to the beachfront tiki bar. Also, casual local eateries like Morada Bay and Lorelei are in short walking distance.

Little Palm Island Resort & Spa, Little Torch Key

This stunning private island retreat will reopen to guests on January 2020, after extensive repairs and renovations following devastating Hurricane Irma. Situated on tiny Munson Island, the Little Palm Island Resort & Spa can only be reached by boat from Little Torch Key or seaplane. The property delivers luxury accommodations that take full advantage of the lush natural landscape. The airy thatch-roofed bungalows come with spacious patios and outdoor showers, while the suites are outfitted with private hot tubs. Thick foliage adds solitude, though the bungalows are fairly spaced out across the five-and-a-half-acre island. There are no TVs or phones in the bungalows, and although Wi-Fi is available throughout the island, guests are encouraged to unplug and enjoy Little Palm’s secluded beaches, pool, and other amenities. Excursions, such as scuba diving in Looe Key, deep-sea fishing, and eco-tours at the Great White Heron National Wildlife Refuge, can be easily arranged.

Casa Marina Key West, A Waldorf Astoria Resort

Located on the southern side of Key West, Casa Marina Key West offers guests a secluded stay with its two oceanfront pools and an expansive white-sand beach. Complete with a poolside bar and grill, plenty of lounge chairs, and beachside service, the resort is well-suited for relaxing as well as vacationing with kids. Upgrading to one of the suites will allow you to enjoy the ocean views from the comfort of your own balcony. Casa Marina is also conveniently within walking distance of the bars and restaurants on Duval Street, plus just a five-minute drive from stellar spots like Zachary Taylor Historic State Park.

Tranquility Bay Beach House Resort, Marathon

Spanning 12 acres on the northern shores of Marathon, Tranquility Bay Beach House Resort is the perfect getaway for guests who want to stay put and relax. The sprawling Victorian-style resort effectively separates guests from bustling Marathon, and two- and three-bedroom suites afford even more privacy. Each of these townhouse-style suites features porches with waterfront views and comfy Adirondack-style chairs, while others offer full-size kitchens. The resort’s on-site restaurants – TJ’s Tiki Bar and Butterfly Café – allow guests to choose between casual beachside and indoor dining. Kayaks and stand-up paddleboards can be rented from Tranquility Bay’s pristine sand beach, where guests can swim or lounge in the clear, calm waters. The waterfront views can be appreciated from the resort’s three pools as well, including an adults-only option and kid-friendly lagoon. Note that exploring outside the resort requires driving. The beaches and marine sanctuary at Bahia Honda State Park and the Dolphin Research Center on Grassy Key are just 15 minutes away by car.

Hawks Cay Resort, Duck Key

Taking up a sizable portion of the 60-acre Duck Key, the 177-room Hawks Cay Resort has recovered from destructive Hurricane Irma with more amenities and contemporary design. The resort’s villas, complete with kitchens and laundry facilities, are well-suited for an extended family vacation, while couples will appreciate the spacious king and queen suites with private balconies. Though there isn’t a ton to do on the island itself, the property packs in plenty for guests of all ages, including five outdoor pools, a saltwater lagoon, a sandy beachfront, seven restaurants, and a laundry list of excursions and activities. Off-property day trips like snorkeling and deep-sea fishing can also be arranged, while Hawks Cay guests also have the opportunity to interact with a pod of friendly bottlenose dolphins that inhabit the resort’s saltwater lagoon.

Southernmost Beach Resort, Key West

With an excellent beachfront location on Duval Street’s more subdued southern end, the Southernmost Beach Resort delivers upscale comfort in a lovely colonial-style setting. Most rooms come with private balconies and rainfall showers, and though not every unit has waterfront views, short pathways lead guests through pristine gardens to a private beach and pier. There are abundant lounge chairs and umbrellas along the man-made sand beach, while the wooden pier is ideal for sunbathing. Yoga classes and spa services can also be arranged on the beach. The resort’s pool has ample lounging space and a poolside bar serving drinks and lunch. Many of Key West’s attractions are easily accessible from the property as well. The Key West Butterfly and Nature Conservatory, Ernest Hemingway Home and Museum, Key West Lighthouse, and Duval Street’s shops and restaurants are all within a 10-minute walk from the property.

Ocean Key Resort & Spa, Key West

On the opposite end of Southernmost Beach Resort on Duval Street, Ocean Key Resort & Spa features stylish, modern decor, setting it apart from Key West’s pervasively kitschy atmosphere. The waterfront property has an unbeatable location for those looking to dive into Duval Street’s vibrant nightlife and restaurant scenes. Fortunately, the resort’s gardens and spa can quickly transport guests into a more soothing setting, while guest rooms with fully furnished balconies and whirlpool tubs make for a romantic retreat. The pool, which includes a hot tub and bar, is set right on the waterfront and grants amazing sunset views. Though guests have Duval Street at their disposal, the resort’s Hot Tin Roof restaurant has a Caribbean-inspired menu worth trying. Other nearby attractions include the Key West Aquarium, Waterfront Playhouse, and Old Town Trolley Tours.

Hyatt Centric Key West Resort and Spa

Just a couple of blocks over from the Ocean Key Resort & Spa, the Hyatt Centric Key West Resort and Spa occupies a more peaceful corner of downtown that’s still within short walking distance of restaurants and bars. The modern resort’s 118 rooms all have private balconies and spacious bathrooms. Nestled between the resort buildings, the pool overlooks the Gulf and provides padded lounge chairs in the shade and sun. The coastal location also gives guests the opportunity to parasail, snorkel, and rent WaveRunners from the hotel marina. Electric scooters and bikes are available, too, so visitors can explore Key West’s historic district and beyond. Following a full day of activities, guests can unwind with massages and skin treatments at the on-site spa. To top things off, the property’s seafood grill is a prime spot to admire the sunset while polishing off an obligatory slice of Key lime pie. It’s also worth noting that the resort is pet-friendly, though there are some weight restrictions.

Key Largo Bay Marriott Beach Resort

The Key Largo Bay Marriott Beach Resort is an ideal getaway for families with kids as well as scuba diving and snorkeling enthusiasts. The 153-room property is comprised of spacious rooms and suites with private balconies, many of which face the Blackwater Sound on Key Largo. Guests can access a private sand beach, but the resort’s sizable pool and whirlpool are better suited for swimming. The on-site dive center makes it easy to arrange scuba diving and snorkeling excursions to nearby reefs. The United States’ first underwater park, John Pennekamp Coral Reef State Park, is a mere five minutes away by car. Just offshore, divers and snorkelers can admire vibrant coral, extensive fish species, sea turtles, and the sunken Christ of the Abyss – an eight-and-a-half-foot bronze sculpture of Jesus. Glass-bottom boat tours are another option for those wanting to discover underwater wonders. Back onshore, visitors can spot crabs darting behind mangrove roots from the elevated boardwalk trail and learn more about this precious ecosystem at the on-site aquarium.