Introduction: Despite play being widely used in occupational therapy practice as a means and ends in intervention, no research has explored how the play of children with HIV/AIDS is affected. Therefore, the specific processes through which play can be used in therapy with children with HIV/AIDS remains underexplored, especially in low resourced settings. This study aims to compare the level of playfulness of children with HIV/AIDS to that of age and gender matched typically developing children living in the same low resourced community. Methods: The Test of Playfulness (ToP) was used to examine the differences and similarities of play between children aged 4–7 years who are typically developing children (n = 52) and children with HIV/AIDS who receive antiretroviral treatment (n = 44). Each child was video recorded playing with a familiar playmate both indoors and outdoors. The videos were scored by two independent raters who were blinded to all aspects of the study. Scores were subjected to Rasch analysis to calculate interval level measure scores. Independent t-tests were used to compare differences between the means of the groups. Results: Typically developing children scored significantly higher when playing outdoors, as compared to children with HIV [t (94) = 3.57, p =.001]. There was no significant difference between mean measure scores for indoor play when comparing typically developing children and children with HIV. Children who are HIV positive scored significantly lower than typically developing children on items related to the ability to suspend reality and framing in both indoor and outdoor environments. Conclusions: Children with HIV/AIDS exhibited lower levels of playfulness when compared to typically developing children. This study provides insight on the play profiles of children with HIV/AIDS, highlighting play deficits and differences between indoor and outdoor play. Occupational therapy can play a significant role in promoting playfulness in children with HIV/AIDS.