Ahhh, Round Hill: the elegant Jamaican hideaway, a favorite for Town and Country fashion shoots, a former pineapple, allspice and coconut plantation, where the elite and moneyed few escape for their tropical respites. The legendary resort, not far from Montego Bay, is an oasis of gardens, secluded beaches, private villas and horizon-edge pools. There's a Spa, tennis, diving, and fine dining, a vacation experience enhanced by the best, most discreet service.

The 36 guestrooms in the Pineapple House were recently renovated and designed by Ralph Lauren, with white stone floors, four poster bamboo beds draped in a white net, 300-thread count Egyptian cotton sheets, and upholstered furniture from the Ralph Lauren home collection. The rooms are all-white, evoking tropical beach living, and with ocean or garden views. The bathrooms were also redesigned by Lauren, with deep soaking tubs, freestanding rain showers, and double sink vanities.