Staphylococcus aureus rarely causes prostatic abscess. We report five cases of S. aureus prostatic abscess in the setting of bacteremia at our institution that occurred between 12/2018 and 05/2019. Three of the cases were caused by MRSA, and four of the patients underwent drainage of the prostatic abscess. All five patients received a minimum of six weeks of antibiotic therapy. One of the five patients died during the course of their infection. S. aureus prostatic abscess with bacteremia is an uncommon but serious disease. Treatment should consist of a combination of prolonged antibiotic therapy and surgical drainage when feasible.