Concierge.com's insider take:
Like a mini-Mustique, this former pineapple plantation on a 110-acre peninsula in Montego Bay is a collective run by the owners of its 29 villas. Past owners have included Noel Coward, Oscar Hammerstein, Bill and Babe Paley, and Viscount Rothermere; these days, Ralph Lauren keeps two villas here (along with a neighboring estate). His influence can be seen in the English country/tropical Wasp decor of the main building called the Pineapple House—the 36 deluxe rooms here have checkerboard floors, blue-and-white striped furniture from his home collection, and bamboo four-poster beds swathed in netting and white linens. The rooms also have ocean views, and all the usual comforts except for TV (there is a common TV room, if you're really jonesing). Most of the villas, which can be rented in their entirety or split into suites, have private pools. Kids are well catered to with a daylong Pineapple Kids' Club, and an annual summer tennis clinic at no extra charge. For the grown-ups, there's a spa with Elemis aromatherapy products and a nightly semiformal dinner at the Seaside Terrace restaurant.