Boylan made her film debut playing a younger version of the title character in the 2001 film Alex in Wonder (a.k.a. Sex and a Girl). In 2004, she starred opposite Alexa Vega and Sara Paxton in the film Sleepover. She starred in her first leading role playing the title character in the 2008 independent film Dakota Skye. In 2011, Boylan starred opposite Tom Selleck as a central character in the television movie Jesse Stone: Innocents Lost.