Half Moon, a RockResort Rating: 4.5 Pearls

Home to 50 pools -- including several used exclusively by villa guests -- this historic retreat still has all the fun comforts of more contemporary resorts, and is a favorite among families.

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Iconic Hotels in Jamaica (2 of 13)

 Home to 50 pools -- including several used exclusively by villa guests -- this historic retreat still has all the fun comforts of more contemporary resorts, and is a favorite among families.
The columned portico at Half Moon's entrance and the marble-floored lobby -- filled with stone lions, crystal chandeliers, and contemporary Caribbean artwork -- highlight this classic resort's breezy yet elegant tone. Home to 50 pools -- including several used exclusively by villa guests -- this historic retreat still has all the fun comforts of more contemporary resorts, and is a favorite among families. Broad common terraces overlook the sea. Made up of simple, two-story buildings carved into the hillside, plus a series of private villas, the small-scale Round Hill hotel offers classic, Jamaican charm -- bellmen wear regal uniforms, the staff address male guests as "sir," and nannies are available for 24-hour childcare. Sweetened air, flirtatious birdsongs, and the all-night frog and cricket chorus that New Yorkers buy for their sleep-wave machines and yoga centers -- that's about all you'll hear in Round Hill's guest rooms, all of which were designed by Ralph Lauren. The fourth wall in every standard room can be opened entirely (and without a screen), allowing guests to sleep to the sound of waves crashing against the shore. Housed in a colonial-style mansion, the spa is removed from the rest of the Round Hill resort by a winding narrow path along the coarse, rocky shore. Only adults are allowed on this side of the property. Located on a remote portion of Negril's western cliffs, the intimate, adults-only Caves boutique hotel has quickly become a Jamaican icon. From the hotel's open-air restaurant, guests can watch the most beautiful sunsets in Jamaica. Opened in 1994 by a Rastafarian artist couple, Bertram and Greer-Ann Saulter, each unique cottage features hand-carved furnishings and whimsical interiors. Pictured here is Moon Shadow, a private two-bedroom cottage. Composed of only five eco-friendly cabins or villas arranged casually around a remote mountaintop, the Geejam -- pronounced "G-jom," -- is a self-proclaimed "private hotel." This means that there is no communal pool or direct beach access, and many guests have all of their meals brought to their rooms. The check-in questionnaire even asks whether guests are recovering from plastic surgery. Drawing such musicians as Bjork, Common, and India Arie, the Geejam houses its own state-of-the-art recording studio. The only common area of the hotel -- which acts as the lobby, the recreation area, and the restaurant and lounge -- is the Bushbar restaurant.
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