Background: Playgrounds are a central resource when it comes to physical activity among minors. This study assesses the association between area deprivation and the quality of playgrounds. Methods: All playgrounds in the city of Mannheim, Germany (145 km2, 311,000 inhabitants) were visited between July 2016 and January 2017 as part of a systematic audit. Each playground’s amenities, attractiveness, cleanliness, and safety were operationalized using well-established, validated instruments. Global and geographically weighted regression models were fitted to investigate the association of the amenities, attractively, cleanliness, and safety of playgrounds with sociodemographic indicators on the social area level. Results: A total of 271 playgrounds were identified. Overall, population density showed the strongest association with all quality variables in the global models, followed by the central official poverty indicator. Significant spatial variation in parameter estimates was found for most of the deprivation indicators with regard to attractiveness, cleanliness, and safety of playgrounds indicating locally negative associations between area-level deprivation and quality. Conclusion: Our findings illustrate the importance of a qualitative approach by analyzing physical activity resources. Concerning the quality of playgrounds, the data from this study support the deprivation amplification hypothesis, meaning that children who are already socially disadvantaged might experience a further contextual disadvantage.