Play skills are a behavioral cusp as they provide the foundation for the development of other related skills in young children. Children with developmental disabilities often demonstrate significant delays in their play skills. When children do not engage in play at the same rates or in the same ways as their peers or siblings, their ability to learn and practice other skills such as communication and social interactions is negatively impacted. We used a concurrent, multiple probe design across participants to assess the efficacy of using a system of least prompts (SLP) intervention package to teach pretend play to three children with disabilities in contexts with their peers. The SLP intervention package was related to increases in target pretend play behaviors for all three children. Also, parents and teachers reported observed changes in play across both the classroom and the home environments.