The Caves (Negril, Jamaica)
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The price tag: $570/night
Outside of Montego Bay in Jamaica is The Caves, a 12-cottage getaway cliffside in a natural preserve. Their bougiest of bougie villas is the Clandestino, a 3500 sq. foot home with access to the caves. There are also five-course dining packages available in private caves, but we’re more inclined to head to the Blackwell Rum Bar, which is located inside actual volcanic cliffs.