Round Hill Hotel and Villas

Round Hill is among the cream of classic Caribbean hotels. Set on a secluded peninsula just west of Montego Bay, this storied retreat combines the genteel air of a country club with the relaxed rhythm of island life. Despite its expansive grounds, the property feels cozy and intimate, with just 36 guest rooms and 27 villas. Rooms in the Pineapple House, which can be connected, have crisp, airy decor and generous bathrooms. Some feature panoramic sea views while others include patios. Fully staffed villas are available as standalone units or split into suites; most have their own pools, and some have flat lawns that are perfect for younger kids to run around. Nanny service is offered around the clock, and the kids’ club provides a daily-changing menu of activities — kids might learn traditional crafts or take a ride on the hotel’s glass-bottom boat while parents savor a spa treatment or afternoon tea. An infinity pool and adjacent kids’ pool sit just a few steps from the small private beach. Service is thoughtful, gracious and very personal. Many of the staff have been with Round Hill for decades, and guests come away feeling like members of the family.