In the 1700s, this historic property on the eastern outskirts of downtown Montego Bay belonged to members of the Dewars clan (of Scotch fame). Its position in the greenery 500 feet above town affords sweeping views of Montego Bay and its harbor from the wide pool deck. (It also means you’ll want a rental car—or taxi fund—to get to the restaurants and beaches below.)

Grace, Gayle, and their mom run the place with cheerful efficiency. Classical columns, poolside statues, and 19th-century, hand-carved mahogany furnishings in the sitting rooms of the Great House lend it the elegant air of a genteel past. Guest rooms are less elegant—nice, a bit fussy, and kind of homey. The one-bedroom suites have French doors onto the terrace, while the Penthouse Suite is actually a three-bedroom apartment with a full kitchen and wide terrace with views over the mountains and the Caribbean sea.  - Reid Bramblett