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This 1950s classic is one of the original Jamaican resorts, a low U of a building set on the perfect curve of private Caribbean beach, where Errol Flynn and Katharine Hepburn once came to play, Winston Churchill to paint, Noël Coward to tinkle the piano keys, Ian Fleming to sip martinis at the bar, and Marilyn Monroe and Arthur Miller to take their honeymoon.

This family-run hotel retains several old-fashioned quirks, such as croquet lessons and a daily afternoon tea. Teddy at the Beach Bar down on the beach has been here since 1958, and has mixed drinks for everyone from Joan Collins to Princess Margaret.

The suites and cottages—some have direct beach access, but even those without an official sea view get a glimpse of the water across the lawns—are large and eminently comfortable, done in crisp white and pale blues with British Colonial wood furnishings and sizeable verandas. None has a TV (or, pointedly, a clock), though there is Wi-Fi. Instead, there is a shared library, long quiet days on the beach, live reggae nightly at the terrace restaurant (which is excellent, and recommended separately), though it would be quite pricey to dine there every night on a meal plan.

To keep things up to date, the Jamaica Inn has been slowly (and smartly) expanding with bespoke cottages and a villa beyond the main buildings, featuring canopy beds and private infinity plunge pools. The most spectacular are the White Suite on its own peninsula, and the two-story, one-bedroom Cottage 7, which opens onto a private cove.

The Jamaica Inn is not exactly adults-only. It's more like "adults-encouraged"; children must be at least 10 years old (12 during the Dec. 15–Feb. 28 high season)

 - Reid Bramblett