Fun on a Weekend (1947)

Peterson Price Porterhouse III (Eddie Bracken)) and Nancy Crane (Priscilla Lane), both flat broke, meet on a Florida beach and decide to "go for the big money," under the premise that perception will turn into reality. They crash into several big houses, pretending they are in the market for an estate, and are soon, although still penniless, living in the best hotel in town, throwing lavish parties and mingling with the upper crust. This is too good to last, but may have anyway if true love hadn't reared its ugly head.