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Fourteen cottages dot the lush property of Dunmore Beach Club—once a private haven for the Duke and Duchess of Windsor—an old-fashioned beach hotel where men wear jackets to dinner and pitchers of lemonade and plates of freshly baked cookies are provided daily. Owners Tony and Cynthia Shogren hired Manhattan decorator Tom Scheerer (who owns a house on the island) to design an elegant guest cottage, the two-bedroom Ocean House. There is also the Shogren’s four-bedroom house, called Sitting Pretty, on five acres adjacent to the resort that is available for guests when the owners are not in residence. Rooms start at $519, with a three night minimum stay required; meals are included.

Who it’s right for: Families with well-behaved children and couples who like a country-club aesthetic.

Who it’s wrong for: People who chafe at old-world traditions like a set dinner hour and a jacket-at-dinner policy.

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Built in 1951, Pink Sands was Harbour Island’s first resort. It operated as an invitation-only hotel until 1992, when it was destroyed by Hurricane Andrew, and subsequently restored by Island Records founder Chris Blackwell. It was not unusual in the ’90s to find barefoot rock stars shooting pool in the main house; complaints of uneven service were commonplace, too. The high-end, hippie house-party atmosphere appealed to some, but not to others. In recent years, the hotel has been managed more as a business, with more emphasis on customer satisfaction. A four-year renovation masterminded by Biba founder Barbara Hulanicki resulted in a somewhat mystical blend of Moroccan, Indian, and Balinese styles. And she came back last year to spruce up her work in the twenty-five pastel-colored cottages scattered throughout the lush tropical grounds, where coconut palm, hibiscus and bougainvillea line the pathways leading to the beach. There are one- and two-bedroom cottages, a small pool, tennis courts. It’s a great choice for laid-back families, who appreciate the relaxed atmosphere but don’t expect the children’s menu, activities or club facilities at more polished Caribbean resorts. Current owners plan to build cottages and villas for private ownership on the property’s pristine twenty acres. Rooms from $600 during high season; a minimum three-night minimum stay is required year-round, and five- and seven-night stays apply in high season.

Who it’s right for: Couples and families who want to be steps from one of the world’s prettiest beaches and who don’t expect five-star luxury with marble bathrooms.

Who it’s wrong for: The hotel’s motto could be “Don’t worry, be happy.” If that doesn’t appeal to you—or if island living in colorful cottages isn’t your thing—this may not be the hotel, or the island for you.

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Originally owned by Lionel Rotcage, son of the Parisian nightclub legend Régine, the Romora Bay Club is an eccentric hotel with a tennis court, a harborside, heated, infinity swimming pool, a bar and cabanas—and a welcoming, if sometimes sassy, parrot named Goldie. Besides the sprawling property’s existing thirty-three guest rooms, private-residence villas are being built here, with sale prices said to begin at $975,000. Rooms from $390 during high season; five-night minimum stay is required during the holiday season.

Who it’s right for: The yachting crowd, as there will be fortyslips to 150 feet completed in 2008.

Who it’s wrong for: Beach lovers; it’s on the bay side.

The intimate Runaway Hill Inn is a peaceful bed and breakfast on the beach that is now owned by former Ranger hockey wonder and Stanley Cup Winner Mark Messier. The building’s British-colonial dormers, backed up by numerous original details, dominate the architecture. In winter, a crackling fire warms the entrance. Each of the bedrooms is different, giving the impression of lodging in a private home—which indeed it once was. The place isn’t fancy, but it’s perfectly comfortable. Each of the rooms are different (and named after Messier family members)—one has a pretty painted Cuban tile floor, there are travertine floors in the villas. At least one has a fireplace. Some have their own terraces with teak furniture.

Who it’s right for: Couples who expect a warm welcome and clean and tidy rooms near the beach and who don’t need much pampering. And families or groups since the villas can accommodate and the courtyard rooms can be joined to create multi-bedroom spaces.

Who it’s wrong for: Those looking for glitz or glamour.