Florida Keys Florida Keys Travel Guide: Best Hotels, Restaurants & Experiences

North America's sole private island resort lies a short yacht transfer from Little Torch Key—aboard a vessel named for President Truman, who once favored this four-acre sanctuary. Thirty suites occupy thatched bungalows styled in British West Indies tradition, deliberately stripped of televisions and telephones. Key deer wander the grounds freely. At SpaTerre, the madrugada massage unfolds in warm shallows, while dinners materialize on the sand under request. Adults only.

Spread across 19th-century wooden buildings next to the Key West Lighthouse and steps from the Hemingway Home, this 45-room inn carries a legacy of LGBTQ+ inclusivity since the mid-1800s. Gardens wrap around a venerable banyan tree, framing a pool where Isabel's Bar serves mojitos mixed to Hemingway's own taste—named for a woman from his life who once resided here. The Hemingway Suite features a wrap-around balcony and deep soaking tub.

Amara Cay captures the barefoot spirit of the Florida Keys with its nature-focused approach and semi-tropical grounds along the Overseas Highway. The resort balances laid-back coastal living with understated refinement—families gather at the firepit for S'Mores while seasonal programming keeps younger guests engaged. A solid choice for travelers seeking relaxed waterfront days without sacrificing comfort or style.

Sprawling across 27 waterfront acres in Islamorada, Cheeca Lodge and Spa has drawn presidents and film stars to its private beach since the postwar era. The generous suites accommodate families with ease, while a dedicated kids' camp keeps younger guests occupied as parents slip away to the pier for bonefishing charters. A Florida Keys institution where laid-back luxury meets genuine outdoor adventure.

Harbour-front rooms at this Key West property frame the island's legendary sunsets, though the prime vantage point remains the pool deck or the fire pit beside the dock, where sand meets toes at twilight. Families find practical appeal in the spacious accommodations and on-site watersports, while the spa offers quieter retreat. A solid base for sunset-chasers who want amenities without pretense.

Spanning 20,000 square feet along Longboat Key's gulf shore, this spa greets arrivals at a Celebration Bar with champagne or wellness shots before guiding them toward oceanfront vitality pools where six hydrotherapy pods face an infinity edge dissolving into open water. The thermal circuit pairs eucalyptus steam with Finnish sauna, while Caroline's Collection rituals layer sound therapy and bespoke scent work into high-performance facials and massages.