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This is the Caribbean good life: a pristine beach, dining rooms opening onto terraces with views spilling over the estate’s 2,200 lush acres, bathtubs set against picture windows with views over the Blue Mountains, and infinity pools where you can stare at the Caribbean horizon as the sun sets over the jungle and sea below.

The Tryall first opened its plantation-era Great House to guests in 1949, and now welcomes outsiders to rent any of its 13 Great House villa suites (one- and two-bedroom) and 74 Estate Villas (ranging from two bedrooms to nine)—whenever the actual owner is not using it, of course. Since each suite and villa is independently owned, each has its own style and decor, though most trend traditional, Colonial Jamaican mixed with modern.

Villas come with a private staff of housekeeper, chef, laundress, gardener, and butler. Your personal chef will sit down with you to figure out a meal plan for your stay, then take care of all the grocery shopping and cooking (expect this to cost roughly another $350 per adult per week). Suites come with just the housekeeper, though you can also hire a chef. The property also has two restaurants. Fifteen of the villas are right on the ocean; the rest are scattered up the hillside (most provide a golf cart for getting around the property, but there’s also a shuttle).

The Tryall is also a renowned 18-hole championship golf course that ambles across the property and comes so close to the beach that the Caribbean itself counts as a water hazard.

 - Reid Bramblett