Holly Madison (born December 23, 1979) is one of Hugh Hefner's recent girlfriends. She appeared in the E! reality television program titled The Girls Next Door in 2005. She is listed as "Hef's No.1 squeeze" on her bio page on Playboy.com. She was a Hawaiian Tropic model prior to become one of Hefner's girlfriends.

Although she has been living with the founder of Playboy at the Playboy Mansion since 2001, she has never appeared in the magazine until 2005. However, Holly shot a pictorial for Cyber Girl of the Week in early 2003. It was posted on the online Playboy Cyber Club before soon being removed. The Cyber Girl photos can sometimes be found on the Internet as they did find their way into some Cyber Club members collections. She appeared on the cover and inside of the November 2005 issue of Playboy along with fellow Hefner girlfriends, Bridget Marquardt and Kendra Wilkinson as the part of The Girls Next Door special pictorial.

She appeared in an episode of Curb Your Enthusiasm as herself along with Bridget Marquardt and Hefner in 2005.