Florida Keys

Hotels in Florida Keys

Even after serving as the backdrop for countless fashion-magazine photo shoots, the Moorings Village & Spa— 18 brightly accented cottages connected to the beach by wooden walkways on a former coconut plantation in the Florida Keys—still seems like your own secret discovery.

This adults-only private resort covers two secluded miles in the center of Old Town. Select five different styles of accommodations for a total of 30 rooms: B&B at The Mansion, cottages, an inn, Manor House, and a townhouse, with concierge services available.

Casa Morada, in the Florida Keys, is the brainchild of partners Lauren Abrams, Terry Ford, and Heide Praver Werthamer, who collectively spent 24 years picking up the tricks of the trade while working at various Ian Schrager hotels.

Built around its own private beach, this mid-range resort provides affordable oceanfront accommodations in the village of Islamorada.

Designed to resemble a large plantation-style home, this resort has 118 rooms, each with tiled-entry foyers and private balconies providing at least partial ocean view.

This boutique B&B housed in a circa-1870 plantation-style mansion is the most graceful place to stay on the island. Beginning in 1930, former owner Peggy Mills spent nearly 40 years on the gardens, adding orchids, palms, winding brick pathways, fountains, and enormous Cuban earthenware jars.

With at least 80 inns and B&B's squeezed onto the eight-square-mile island, Key West may well be America's most "inn" town. So what makes the Mermaid & the Alligator stand out?

Just off Duval Street, hidden behind palms, the inn feels like a tropical island oasis. Some of the cheery cottages have lounge-worthy verandas.

The oceanfront property newly reopened with its stellar snorkeling program intact. Stay in one of 212 tropical-chic rooms then dine at the Atlantic's Edge restaurant, where the chef will prepare your own catch.

1884 clapboard houses set back from busy Duval Street. A no-cell-phones-in-public-spaces policy helps to keep the peace.


One-third down the Florida Keys is Islamorada, known as the sport-fishing capital of the world and home to the Chesapeake, a 65-room property that has grown from an old-school seaside motel into a resort that caters to anglers and families.

The quirky property features six airy cottages (and one regular room). Its eccentric owner will loan you books from her personal library for enjoying in the surrounding hammocks.

One of the most photographed Key West homes for its accurately restored Colonial Queen Anne architecture, this Old Town hotel is known for its historic columns and gingerbread elements. This six-room guesthouse has been in operation for more than 30 years and now sports purple shutters and rockin

Six low-rise buildings, tucked into bougainvillea gardens between the harborfront and the historic Old Town, house 142 guest rooms and suites.