Review By: Kevin Brouillard
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.
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.
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.
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.
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.
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.