The Best Hotels Near Oleander, by the Record
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Two miles of white sand beach, a Robert Trent Jones Sr. golf course, and an equestrian center suggest that Half Moon in Montego Bay has strong opinions about keeping guests occupied. This sprawling Forbes Four Star resort opens onto the Caribbean through a breezy, open-air lobby where Blue Mountain coffee arrives before you've worked out where you're going. Villas, suites, and original cottages scatter across the grounds, and the staff greets you by name from the first moment.
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Ralph Lauren owns one of the villas here, and while it's off-limits, he did design the hotel lounge, which tells you most of what you need to know about the atmosphere. This Montego Bay resort holds a Michelin Key, and sits somewhere between old Caribbean money and effortless informality, with privately staffed villas, sea-facing suites, a quiet beach, and service formal enough to make you sit up slightly straighter.
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Twelve thatched cottages perch on a cliff above Negril's west end, and the volcanic caves carved into the rock below can be booked for a candlelit dinner or explored by swim. This small, adults-leaning resort holds a Michelin 2 Keys distinction and leans hard into seclusion: meals made from local organic produce are included, and the pace is entirely self-directed. The saltwater pool, hot tub, and open-air spa all face the Caribbean.
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A cluster of villas perched on the cliff edge at Pristine Cove, Jamaica's westernmost point, where the horizon pool is carved into the bluff and appears to continue all the way to Mexico. The suites hang over the water with outdoor showers and sunset views that make the big all-inclusive resorts feel like a category error. Four-poster beds, muslin netting, ceiling fans, and a poolside bar doing the heavy lifting socially. The Michelin Guide awarded it one Key.
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The cottages at this low-key boutique hotel on Jamaica's south coast look like they happened by accident, in the good way: mismatched, sun-worn, and a few of them with outdoor tubs on sea-view decks that feel like lucky finds rather than amenities. The Michelin Guide has selected it. Getting here takes some doing, but locals and guests share the same pool and the same cheap beers, which is the whole point.