Half Moon 4.5

Montego Bay, Jamaica
Broad common terraces overlook the sea.

Iconic Hotels in Jamaica(3 of 13)

 Broad common terraces overlook the sea.
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.