My third tactic for achieving the affordable beachfront villa was to rent a property with adjustable rates, where the price depends upon how many bedrooms you occupy. Such arrangements are common in the Caribbean: You can pay a lower rate by renting only a portion of the rooms, yet you get the entire property to yourself. The Coral Beach Club has such sliding rates, so we were able to reduce the $1,062 even further by renting just two bedrooms for $798 per night (including housekeeping and tax). I also sought out a property that allows stays of fewer than seven nights. Many owners—especially in Europe—insist on a seven-night minimum, often from Saturday to Saturday. When you're trying to snag cheap airline tickets, however, date flexibility is key. Because the Coral Beach Club allows rentals of six nights, I managed to reduce my airfare from New York to $328 per person. (Renting for seven nights would have doubled the airfare.)

My most important strategy, however, was to seek the guidance of a villa rental agent who knew my destination like the back of her hand and could match me to the right location and residence. Marilyn Pulito of Villas in Paradise, whose sole focus is St. Martin/Sint Maarten, owns a home on the island and has spent every winter there for the past 25 years. Not only did she steer me to Oyster Pond—which provided quick access along picturesque roads to the most charming spots on the French side of the island—but she also picked a beach suitable for kids (Dawn Beach, perfect for bodyboarding) and a property with every amenity on our wish list (free no-hassle Wi-Fi above all). She knew that the Coral Beach Club was offering a special pay-the-low-season-rate-in-high-season deal, and she suggested villa No. 5, Starfish, because it's on a relatively private, peaceful section of the beach.

What did I give up to get this bargain? Well, I did not get the silky, flotsam-free white sand beach with a calm glassy sea that I would have gotten on, say, Anguilla—where a beachfront two-bedroom of equivalent comfort and appeal, Meads Bay Beach Villas, would have cost me $1,080 per night, including tax (versus the $798 I paid). I did not get the picture-postcard panoramas unmarred by high-rises in the distance that I could have gotten on, say, St. Barts—where the charming beachfront home I might have rented, Crystal Dream, had a two-bedroom rate of $1,178 per night. Nor did I get the glamorous seclusion—the virtually private beach—that I could have gotten on St. Martin itself had I rented a villa such as La Vie en Bleu, located on the spectacular strand at Baie Rouge, for a whopping $1,807 per night.

For $798 per night, however, I don't think I could have done better than Starfish. My family was more than happy to put up with a few passersby on the beach in exchange for the convenience of having several restaurants, a beach bar, a small grocery store, and the activities of Oyster Pond Marina only a short walk away, and we sacrificed nothing in the way of comfort. Our villa's gleaming kitchen was outfitted with all manner of gourmet touches, from stainless steel Viking appliances to a custom-built wine cooler. The living room had a 50-inch flat-screen TV with a gazillion channels, surround sound, and a DVD player, as well as a dining area with a formal glass table and seating for eight. Each bedroom had an enormous closet, a 32-inch flat-screen TV, and a sleek en suite bathroom. The pool terrace had six overstuffed chaise longues, four huge armchairs, and a dining table with eight more chairs, yet it was so spacious that the furniture seemed to disappear entirely. One of our favorite touches was an outdoor shower (for washing off sand) that opened into the indoor shower attached to the master bedroom. Mid-pool was a sunken gazebo—accessible via a little walkway from the terrace—where you could lounge on pillows, enjoying a cocktail and the ocean view, yet remain dry and shaded from the sun. The sand-colored travertine floors both indoors and out meant that the only thing distinguishing the interior from the terrace and the beach was a glass wall, and when you looked through it from the living room or the master bedroom, the glorious view was of nothing but pool, sand, and sea.