This has been the five-star luxury resort of Montego Bay ever since it opened in 1953 with Noël Coward as the first shareholder of a private villa on 30 acres of jungly gardens and blooming frangipani and jasmine on a small, private beach. (There are another 10 acres on the next cove over where the spa occupies the rebuilt remains of the plantation’s original stone manor house.)

Round Hill aims for that private island feel, and is a place to relax: There are no TVs in the rooms (though there is shared one in a lounge). Breakfast, cooked to order, is served on your own villa, afternoon tea is complimentary, and the James Beard Award–winning chef makes use of the hotel’s own organic garden for his upscale Jamaican cuisine at the restaurant (recommended separately).

The guest rooms in the Pineapple House, overlooking the infinity pool and oceanside sundeck, were remodeled by shareholder Ralph Lauren in a dark wood, bamboo, and rattan luxe–Caribbean look. There are also 27 villas—mostly two- to four-bedroom, but a few larger Luxury Villas—and, when the villa’s owners are not in residence, you can rent the entire villa or a suite within it. Each villa comes with its own pool (shared only with anyone else staying in one of that villa’s other suites), and each varies with its owner’s taste and style.

Would you prefer Villa 12, where Oscar Hammerstein met Maria von Trapp and was inspired to write The Sound of Music, or Villa 10, where JFK and Jackie spent their honeymoon? You might already know what Villa 11 looks like, since it was the setting for the film version of How Stella Got Her Groove Back. Oh, and Sir Paul McCartney favors Villa 17 for family vacations.

(It’s not readily apparent, but if you click on the “Property Map” on the property’s website, you can actually see detailed layout plans of each villa along with photographs and links to even more pics on the Facebook page.)

 - Reid Bramblett