Originally opened in 1953, Round Hill Hotel and Villas was conceived by a respected Jamaican-born entrepreneur, John Pringle. Round Hill comprise 27 individually owned villas and the 36-room Pineapple House surrounded by 110 acres of lush tropical gardens. Designed by Ralph Lauren, The Pineapple House features 36 oceanfront guestrooms overlooking the Caribbean Sea and the double infinity edge pool. The upper level rooms have spacious vaulted ceilings and large louvered windows which fold back to take full advantage of breath-taking views. The lower level rooms have spacious patios or balconies.The villas feature two through six bedroom suites, living rooms, verandas and magnificent views. Twenty-three of the villas have private pools. Each villa bedroom is ensuite with its own bathroom and terrace. Guests may book a private, complete villa with private pool and dedicated staff or individual villa suites can be booked, ranging from Classic Villa Suites to expansive Grand Pineapple Suites, most of which provide access to uniquely designed and lushly landscaped villa pools.