Concierge.com's insider take:
Jamaica is famous for its luxury rentals, many of which are villas staffed by maids, cooks, gardeners, and butlers. Most come with swimming pools and anywhere from two to eight bedrooms (a few, in fact, are mini-palaces with their own helipads or tennis courts or—in one case—a recording studio). Some are located along the beach, others in the countryside. Still others, like the 77 villas at Tryall Club, near Montego Bay, offer the best of both worlds—verdant privacy, and also full-scale resort facilities at their doorsteps (876-956-5660; www.tryallclub.com).
The best source for information on rental villas in Jamaica is Villas by Linda Smith; her website provides a virtual tutorial on villa vacations and costs. A reminder: Though the rates might seem extravagant at first, once you've divided by the number of guests and the number of nights, you may find them a steal (301-229-4300; www.jamaicavillas.com).