Location: Wainscott, N.Y.
Price: $450,000 per month
Square footage: 25,000 square feet

Jay Z and Damon Dash caused a stir on the East End in the summer of 1999 when they rented this 25,000-square-foot mecca for two weekends. Goose Creek mansion, situated on an inlet off of Georgica Pond, boasts a 110-seat movie theater, an indoor heated wave pool, and a Turkish bath among a whole roster of glitzy amenities. Jay Z claims that he “felt like a little kid in a big haunted house in there.” 

Others notable visitors who have stayed in the house include Madonna, Jennifer Lopez, and Billy Joel.