Bennett was born as Haley Keeling in 1987 in Fort Myers, Florida and grew up in Naples, Florida. She attended Stow-Munroe Falls High School in Stow, Ohio, then studied music and acting while attending Barron Collier High School. After graduating, she and her mother moved to Los Angeles, California to pursue her career in the summer of 2005.

Bennett's debut film role was the pop-sensation character Cora Corman in the 2007 romantic comedy Music and Lyrics, opposite Hugh Grant and Drew Barrymore. She has signed a three-picture deal with Warner Brothers Pictures and is currently filming her second movie "College."

Haley appeared in the February 2007 issue of GQ magazine in the GQ/Features section.

Bennett sang several songs for the Music & Lyrics soundtrack, including "Slam," "Way Back Into Love," "Entering Bootytown," and "Buddha's Delight."

In 2007, she signed with 550 Music/NuSound Records (part of the Epic Records family of labels), and began working on her first album with the aid of singer/songwriter Shaley Scott.