Round Hill Hotel and Villas is situated on a lush 110-acre peninsula in Montego Bay, Jamaica. With such notable guests as John F. Kennedy and Paul McCartney, the resort has long been a legend in the Caribbean and continues to exude timeless glamour and low key luxury in a stylish setting. Guests can stay in one of the 36 Ralph Lauren-designed rooms in the Pineapple House or a selection of 27 private, 2-6 bedroom villas. Other highlights include open-air dining on the terrace, a fabulous infinity pool, five all-weather tennis courts, and an incredible spa located in a beautifully-restored 18th century plantation house. www.roundhilljamaica.com