The luxury and price of a villa can beat that of the best hotel

At St. John and other Caribbean hot spots, a week's stay at a villa can be cheaper and more luxurious than even the best hotel room

The benefits to renting a villa begin at the airport. There you will sit in the departure area and survey your fellow passengers, inevitably a kind of Peterson’s Field Guide to Caribbean flotsam and jetsam: the knots of senior citizens on their way to meet cruise ships; the frat boys in Señor Frog T-shirts; the would-be Jimmy Buffetts with leathery faces and thinning ponytails; the moms already applying sunscreen to their screaming kids and the dads already plotting their escape to a fishing boat or golf cart. You will look around at them and whisper to yourself, “After this flight is over, I will never see any of you people ever again. Not at the pool. Not at the reception desk. Not at breakfast. Never.”

While your cabinmates are checking in at the local upscale resort, you’ll be wandering through room after impeccably decorated room of your villa trying to figure out which one has the best view of the ocean from its private balcony. And if you’ve played your cards right, you and your handpicked companions may have paid less for your accommodations than the resort crowd did. With four bedrooms, St. John’s Hakuna Matata averages out to just $370 per night per couple—in the high season. Compare that to the nearby Westin St. John Resort, where the rack rate can be as much as $700 per night.

But beyond cost (and even beyond the undeniable tingle that saying the words “my villa” provokes), there’s a vast aesthetic difference.

A villa is somehow of a place—integrally part of the landscape—an authentic alternative to the McLuxury served up by even a well-meaning hotel chain. To stay in a private residence puts you in a community, not only of your neighbors and the locals you’ll meet at the market, but of a sort of “villa-ocracy” whose members have known how to travel right through the ages: from Italian counts relaxing in the hills of Tuscany to David Letterman taking a break on St. Bart’s.

As you may have imagined, the inaugural, stock-up trip to the liquor store is one of the great rituals of villa life. So are a host of other, usually boring, domestic chores. Like ending an evening of picking out constellations in the hot tub by throwing your bathing suit in the dryer, so it will be ready for the beach in the morning. Or telling the cook the snacks you had in mind for tomorrow’s poolside backgammon tournament.

Eventually, of course, you will deign to come down off the mountain and spend a few hours snorkeling across impossibly blue water or riding a horse over wild green hills or just lolling in the sand. And then, pleasantly sunburned and weary, you will return to your villa—up the dirt road and past the gate and up the long driveway—and, inevitably, someone will sigh happily and say, “Ah, home.”

And, for a week at least, they’ll be right.