Studies have been conducted on the association between physical activity (PA) and sleep, but to the best of our knowledge, a simultaneous analysis of the effects of occupational PA (OPA) and leisure time PA (LTPA) on South Korean firefighters’ sleep has never been conducted. This study aims to analyze how OPA and LTPA affect these individuals’ risk of suffering from insomnia with-in this specific population of subjects. The study includes data from an online self-report survey in which 9788 South Korean firefighters participated. The survey used the Insomnia Severity Index and the OPA- and LTPA-related characteristics were investigated. The independent two-sample t-test, χ2 test, and multiple logistic regression analysis were performed. Subgroup logistic regression analyses were also completed in accordance with the OPA level. Among 9788 participants, 890 (9.1%) suffered from insomnia. A logistic regression analysis revealed that higher levels of feeling of job loading (FoJL), rising levels of physical strength utilization rate (PSUR), greater frequency levels of occupational activities, and high-intensity LTPA were significantly correlated with an increased risk of insomnia, while execution of LTPA and getting enough rest after LTPA was correlated with a decreased risk. However, the subgroup analysis showed that high-intensity LTPA was correlated with a significantly increased the risk in the group with high OPA, but this did not apply to the group with low OPA. Although the risk of suffering from insomnia was overall significantly higher in the high OPA group, the risk was significantly lower in groups getting enough rest after partaking in LTPA, regardless of the OPA level. Thus, the intensity of exercise programs pre-scribed to groups with high OPA and individuals with higher risks of suffering from insomnia, such as firefighters, police officers, and soldiers, should be considered.