Florida Keys Private Island Escapes

Accessible only by water, these resorts deliver a lifestyle of barefoot luxury


Any trip to the Florida Keys is a visit to the islands. At the southern tip of Florida, U.S. Highway 1 takes to the water to become the world’s longest overseas highway, where drivers leapfrog across 31 islands and 40 bridges on a 110-mile journey to Key West. But for every island that can be reached by road, there are many more that can’t. Most are small and unsettled, but a select few hold boutique resorts and secluded private homes that can only be reached by boat. Here are three of our favorites.

Sunset Key Cottages

Just a quarter mile across the water from the bustle of downtown Key West, the Sunset Key Cottages offer a very different resort experience. This 27- acre private island is home to a vacation village made up of 40 individual cottages, each immaculately finished in classic island styles. A motor launch shuttles guests from the affiliated Westin Key West Resort & Marina to the island’s dock. Ashore, there are no cars, just bikes and golf carts. Shaded pathways connect the community and lead to beaches and resort amenities such as the pool, fitness center, and the waterfront restaurant Latitudes, which is known both for fine food and one of the best sunset views in the Keys.

Key West Sunset Key View From Balcony

The view from a four-bedroom cottage at Sunset Key. Here, guests enjoy the perks of private island living, but are just a short boat ride away from all the attractions of Key West. Photo: Sunset Key Cottages

The Sunset Key guest cottages are designed to be self-supporting, with fully equipped kitchens, living and dining areas and modern amenities. Larger cottages also feature private plunge pools. Guests are provided with a range of resort services and amenities, including 24-hour room service and concierge grocery shopping. Books, games and movies are available through the concierge, and children’s fishing poles are provided for use off the dock. Among the island’s unique perks are morning breakfast basket delivery of fresh fruits and pastries, and fresh-squeezed juices placed in cottage refrigerators at evening turndown. A favorite with youngsters is the ice cream cart that makes daily rounds with complimentary frozen treats, while adults are also indulged with evening rum tastings.

Sunset Key Cottage Interior

The contemporary Key West decor of a Sunset Key Cottage is designed to showcase expansive water views and blur the line between indoor and outdoor living spaces. Photo: Sunset Key Cottages

Little Palm Island Resort & Spa

Coconut palms rustle in the sea breeze. Clear waters lap against a white sand beach. Thatch-roofed bungalows sit surrounded by flowering tropical plants. If you arrived blindfolded, you might think you’d been transported to the South Pacific. These scenic similarities weren’t lost on the film crew that once used the site as a stand-in for the Solomon Islands when filming the movie PT109. Now named as one of the world’s best small resorts, Little Palm Island Resort & Spa has seen its share of CEOs, celebrities and even former presidents. But there’s nothing pretentious or exclusionary about this five-acre oasis of barefoot luxury, where sun, sand and good living set the tone.

Little Torch Key Little Palm Island

The shores of Little Palm Island are ringed in swaths of white sand and shaded by tall coconut palms. Coral reefs and blue waters lie just offshore. Photo: Sammy Todd Dyess/Little Palm Island

Guests arrive aboard the resort’s launch, and follow paths of crushed seashells through a garden environment to their private bungalow suite, where chilled champagne awaits. The West Indies-inspired decor invites relaxation and intimacy, with vaulted ceilings and a custom king bed set under draped netting. There are no phones or televisions to distract, and the emphasis is on features such as private terraces, outdoor bamboo showers and boudoir tubs. As would be expected from a world-class resort, there is an on-site spa and an award-winning restaurant. Guests can also opt for in-room dining and private meals served in beachside settings. The concierge staff can coordinate a wide range of activities such as fishing, snorkeling, kayaking, sailing and birding, but many guests are content with a book and a hammock.

Little Torch Key Spa Resort

Bungalows at Little Palm Island include separate sitting rooms, many with direct water views. Additional en suite amenities include private decks, outdoor showers and soak tubs. Photo: Little Palm Island

Seabird Key

This is the ultimate in private island living. A five-minute boat ride from the town of Marathon brings guests to a ten-acre island occupied by a single island-style home. The interior is finished in rich natural woods, with large windows to bring in water views. Each of the four bedrooms opens to a private deck, and there are additional porches for relaxation and ocean view dining, plus a rooftop widow’s walk that is a favorite spot for taking in sunsets. The owners of Seabird Key are dedicated to sustainable practices. The entire island is off-grid, employing a sophisticated solar energy system for electricity and hot water, rainwater capture and grey water irrigation and both organic and inorganic recycling programs. But going green does not mean giving up creature comforts, as the home offers all the expected amenities of modern living.

Marathon Seabird Island

Though just minutes from civilization by boat, Seabird Key provides a sequestered natural environment that can become a refuge or a starting point for water sport adventures. Photo: Seabird Key

With coral reefs, back country lagoons and blue water all just a short cruise away, guests at Seabird Key can take advantage of the island’s complimentary flotilla, which includes kayaks, a sailing catamaran and a 19- foot powerboat. There is also room for guests to tie up their own boat. Ashore, pathways throughout the island’s wooded interior lead to sandy beaches and shaded hammocks. The landscape is a haven for nesting pelicans, herons, ibises, cormorants and ospreys. Complementing this natural setting is easy access to services. A dedicated offsite manager is on call, and guests who opt for additional services can enjoy perks such as pre- stocked foods and scheduled visits from private chefs and yoga instructors.

Seabird Key Marathon Keys

Rich natural woods are showcased in the master bedroom of the home on Seabird Key. This private residence can accommodate eight guests, who have a ten-acre island all to themselves. Photo: Seabird Key