I was learning lesson one in the art of renting the perfect villa: A cool Web site does not a knowledgeable rental agent make. In fact, the inverse seemed to be true: The more villas and countries in an agency's portfolio and the slicker its marketing and Web presence, the less the rental agents knew about the villas they represented. As I later found out, since the owners of many of the best homes insist on discretion and privacy, their representatives often have private Web sites accessible only with a password.

I was not willing to entrust my family's happiness to a villa rental factory. So after thirty-nine hours of research, frustrated and out of time, I threw up my hands in despair and ordered my husband to take over. His research method took all of ten seconds. He typed "kid-friendly villa Tuscany pool cook" into Google, and there it was: a restored farmhouse called Casa di Monti, near Gaiole in Chianti. It did not have everything on my wish list, but it had enough, and I was thrilled to read about "Delia, the superb local cook" and the "pool with electric cover [that] is completely child-friendly" as well as warm enough for "those adults who love an early-morning dip."

I contacted the rental agency, a British firm called JCJourneys. Although the property sleeps twelve, it turned out that we could have just the main house, with its four bedrooms and four bathrooms, at a lower rate (and the agency's assurance that the other two houses would not be rented out). I was relieved to find that the JCJourneys agents, Cassian Roberts and his wife, Jane, had actually visited the villa and have small children themselves. But I was distressed at the price: $8,464 for one week (which included a cook for three hours a day and a maid for four, Monday through Friday). Cassian offered to talk to the owner to try to get it reduced. He came back with a rate of $5,408, which I took, having learned lesson two in renting a villa: If you're going in low season or booking at the last minute, ask if the price is negotiable. Bear in mind, however, that the finer the villa specialist, the more in-demand the house and the less flexible the rate.

Two and a half weeks later, we landed in Italy, where I promptly learned lesson three: If you're going to drive an unfamiliar car on foreign roads after a sleepless transoceanic flight, use a rental agent who provides reliable directions. For instance, if your instructions say to drive 11 kilometers past Gaiole and turn left at the sign for Castello di Brolio, Castello di Cacchiano, Monti, and San Marcellino, would you (a) take a left 9.8 kilometers past Gaiole at the sign for "Castelnuovo B., S. Martino al V., S. Regolo, Monti, Brolio," (b) turn left 12.4 kilometers past Gaiole at the sign for "Monti, San Marcellino, Brolio," or (c) faced with two screaming kids who have spent twenty-four hours strapped into plane and car seats, phone the house manager at the villa? We chose (d) all of the above, only to discover that both the phone number and the house manager's name on our instruction sheet were incorrect. For that matter, so was the villa's name. The locals know Casa di Monti by its real name, Sole di Sesta. Lesson four: Most villas are represented by several different agencies—and rechristened by each to keep prospective customers from price shopping—so insist that your agent include the villa's real name in your driving directions.