Grab some (wealthy) friends and form your own modern-day Rat Pack by renting out Sinatra's Palm Beach home, Twin Palms. The 4,500-square-foot, mid-century home, which was designed for The Chairman in 1947 by Stewart Williams, has four bedrooms (each with its own bathroom, natch), a pool and a few more, er, personal traces. The house has witnessed a number of Sinatra's parties and a few of his legendary blow-ups. He once tossed wife Ava Gardner's belongings out onto that very driveway, and a chip remains in one of the sinks from when Frank hurled a bottle in a rage. Bada-bing!
Rates: $1,495$2,600 per night.