Adolescents and young adults with disabilities experience several health inequalities and challenges in maintaining healthy lifestyles. As a group, individuals with disabilities experience higher rates of obesity compared to youth without disabilities. This study was designed to examine the types of challenges experienced by youth with disabilities and parents of youth with disabilities in maintaining a healthy lifestyle. Strong evidence indicates that having a healthy lifestyle and preventing obesity are not only the result of an individual's behavior related to physical activity and consumption of healthy products but also several complex factors in the person's environment. This study was designed to understand the perceptions of youth with disabilities and their parents about the challenges they experience in engaging in physical activity and consuming healthy products, and ideas and strategies for promoting healthy lifestyles. Overall, youth with disabilities lack access to opportunities for engaging in physical activity as well as access to affordable foods. Implications for systems and policy changes are discussed.