Surrounded by a 100-acre plantation that once produced pineapple and coconuts, Round Hill cascades past stately palms and magical gardens down to its own pristine crescent beach.
Renowned for being one of the most exclusive properties in the Caribbean, the resort is a long-standing icon with a celebrated legacy and legendary tales including how Oscar Hammerstein met Maria von Trapp and "The Sound of Music" was written there. John F. Kennedy and Jackie Kennedy honeymooned in one of the villas the year the property opened and regularly returned for holidays; on one such occasion JFK edited and rehearsed his now famous inauguration speech by the pool.
There are 36 spacious Oceanfront Rooms in the Pineapple House, downstairs with balconies and upstairs with cathedral ceilings. Rooms are designed by Ralph Lauren and evoke tropical living with four poster beds and sumptuous upholstery. They are air-conditioned and have louvered windows to take full advantage of the view.
The Superior, Deluxe, Master and new Pineapple Villa Suites are in 27 villas dotted around the hillside and have private living rooms or verandas and magnificent sea views. Deluxe, Master and Pineapple Villa Suites have a shared pool. Complete Villas can be rented with a private pool for up to ten persons.
There are two restaurants, the Grill hosting a twice-weekly Farm To Table dining experience and Jamaica Night each Friday, celebrating Jamaican food and culture with live entertainment
This hotel has been welcoming the literati and glitterati since 1953 and it's easy to see why.