Michael Bloomberg (8): Vail, Colo.

New York mayor Michael Bloomberg—the 8th-richest American, according to the latest Forbes report—interpreted the old saying "go west, young man" quite literally, when he bought a vacation home in the lavish ski resort town of Vail, Colo. Bloomberg frequently dines at Vail Mountain's exclusive Game Creek Club—where members pay an exorbitant $50,000 initiation fee—with others in his league. But he doesn't like to stick to one spot every time the urge to vacation strikes. He also owns a $10 million Victorian townhouse on London's Cadogan Square, a sprawling Westchester estate in Armonk and a $10.5 million mansion in Tucker's Town, Bermuda, that fronts the ocean. This is when having a private jet comes in handy.