The Big Bounce (2004) on Netflix

Jack Ryan, a charming but mischievous kid with a history of small cons, never nasty, as he always approaches life from the pleasant side, goes to surfers paradise Hawai, where dodgy district judge Walter Crewes enlists him to get to real big criminals. Jack finds himself teaming up in bed and thieving 'business' with Nancy Hayes, the greedy mistress of evil hotel magnate Ray Ritchie and his dumb lieutenant Bob Rogers, Jr. and a real temptress gold-digger but is about the only one without an hidden agenda...