The most important step I took, however, was to articulate to Paul Mermelstein of Island Hideaways—a Caribbean rental agent who made my 2006 and 2007 lists—exactly what I was seeking. The villa he recommended, Bienvenue, is near Montego Bay, just up the hill from the Half Moon Resort's golf course and close to the Ritz-Carlton and the Rose Hall Resort & Country Club. Mermelstein detailed the drawbacks of the villa: It's an older house, the bathrooms are outdated, the furnishings are not luxe, only the bedrooms have AC, and there is just one television and phone. However, he pointed out, the villa is well-maintained, the owners are "very conscientious," and, considering everything you get—the staff of five and use of the Rose Hall Resort's beach and facilities—it's a great value. Value in a villa depends on how the owner prices it, he explained, and Bienvenue's owner prefers to price it a little lower than what the market will bear in order to rent it more often.

I had two hesitations. One was Jamaica's high incidence of crime, both petty and violent. Mermelstein assured me of the villa's safety—it's in a peaceful residential neighborhood, several of the staff live on the premises, and a security guard patrols at night (Jamaica's tourism board assigns a guard to every villa in the country). My second concern was that a staff of five sounded like overkill: I couldn't imagine needing more than a cook and a housekeeper. On the other hand, I figured, the larger the staff, the greater the entrée I would have into the local culture and customs—which, in Jamaica, are rich and rooted in the island's history. I overcame my hesitations when it became clear that Mermelstein has a great rapport with Bienvenue's owner, since a close relationship between rental agent and owner is, as I discovered last year, key to a superlative experience. What also impressed me is that Mermelstein offered a van and driver for the week for $750—a good value, considering how expensive Jamaican rental cars are, how nerve-racking the roads are, and how helpful our driver, Roy, turned out to be. Roy kept us safe and was available whenever we wanted him, day or night.

The villa drawbacks cited by Mermelstein actually ended up being pluses for us: We loved the house's tropical architecture and old-fashioned feel, finding its ambience far preferable to that of a modern house. Air-conditioning in the open-air living and dining areas proved unnecessary because there was always a pleasant ocean breeze wafting through. Indeed, we never once turned on the AC anywhere in the house. The large staff ended up being a great advantage too, since any extra time they had on their hands was time they could spend with us. Valin Wright, the butler, showed Charlie and Doug how to pick flowers and taught them all about dwarf bougainvillea, surprise bougainvillea, African tulips, ixora, croton, hibiscus, desert orchids, and more. Elaine Harding, the housekeeper, showed them how to make swans out of white bath towels. Melvin Robinson, the gardener, gave us a horticultural tour of the three-acre property's trees and plants: breadfruit, sugarcane, sweetsop, soursop, green bananas, plantains, limes, cherries, June plums, coconut palms, bamboo, and five different types of mango. Naomi Lewis, the cook (who delighted our sons with pasta and Jell-O nightly and even got them to love green beans), taught the boys how to pick gungo peas, which she then made into a yummy Jamaican rice-and-peas dish. Val and Melvin pointed out the birds around the property—parrots, baldpates, pea doves, ground doves, woodpeckers, and "doctor birds" (a type of hummingbird whose two-pronged tail reminded eighteenth-century Jamaicans of the split-tailed coat worn by doctors). They also suggested that we take the kids to a nearby sanctuary where they could hand feed doctor birds. We did, and it proved a highlight of the trip.