You're on vacation, stretched out on a beach chair in Hawaii, a long day of surfing under your belt, a piña colada in one hand, and nothing to do till dinner rolls around…. Then you remember that flyer you got—two free tickets to tonight's food-and-alcohol-centric luau if you sit through a timeshare presentation. How bad can it be?

When you wake up the next morning, you vaguely remember the salesperson talking about fixed weeks, points, and deeds and you realize that you just bought a timeshare.

Timeshares once had the reputation as the vacation industry's used car lots, complete with slick salespeople, confusing language, lemons, and post-purchase headaches. They first appeared in Europe in the 1960s—vacation spots where owners buy an incremental share of a property, usually a week each year. But changes in the timeshare industry in the last two decades have made timeshares an increasingly popular choice. In 1990, $1.2 billion worth of timeshares were sold; in 2004, sales increased to $7.87 billion, according to research by the Washington, D.C.-based American Resort Development Association (ARDA).

Your Piece of the Pie

With more and more A-list resorts offering up fractional ownership opportunities, living the dream on some of your favorite powder grounds and being pampered like a rock star is becoming a reality.

Timeshares have sprouted everywhere, from South Pacific beaches to the Colorado Rockies' ski slopes. Urban meccas like London, Hong Kong, and New York City have timeshares that swap beach chairs and ski-in lodging for high-energy nightlife and theater. "Wherever the hot vacation spot, the timeshares are sure to follow," says Ray Jacobs, editor of the magazine Timesharing Today.

As always, the stalwart attractions of timeshares remain constant. First, they're a sanity-inducing solution to vacation travel. Unlike those who own a second house, who spend part of each vacation—or considerable cash—on upkeep, an annual timeshare maintenance fee gets the lawn mowed, the roof fixed, and the kitchen clean before an owner arrives. Second, timeshares get people in the habit of vacationing. If you've pre-paid for your vacation, you're much less likely to skip it. "A lot of the spouses of workaholics think it's the best thing that ever happened to them," says Howard Nusbaum, ARDA president.

But flexibility is the biggest draw in today's timeshares. Despite expectations to the contrary, many timeshares now give participants the choice of vacationing any time during a certain season. Savvy timeshare owners can exchange weeks at their home resort for vacations at timeshare properties around the world. Timeshare weeks can even apply toward cruises and plane tickets.

Diving into timeshare vacationing can open up a world of possibilities, says Lisa Ann Schreier, a former timeshare salesperson who now runs the consulting company TimeShare Insights. But Schreier says it's important to do your homework first. You need to know what you're getting into before you sit through a sales pitch or write a check to a reseller. "If it sounds too good to be true, it usually is," she says.