Background Plantar heel pain (PHP) can be a common medical complaint among people with both sedentary and active lifestyles due to varied causes. It can affect the quality of life and result in significant disability. Despite many studies on PHP, few have focused on a specific population, such as school teachers. School teachers represent a significant proportion of the population of Medina, and addressing such a complaint and its possible relevant factors, which are most likely to be common among them due to their comparable job duties, will aid us in determining the relationships between personal characteristics, work-related factors, and PHP, as well as in formulating management plans. This study aims to identify the prevalence of PHP and its determinants among school teachers in the Medina region of Saudi Arabia. Methodology This cross-sectional study aims to identify the prevalence of PHP in school teachers. It was conducted in the Medina region of Saudi Arabia. A self-administered, online, validated questionnaire was created and used for data collection. Consent was taken from all participants before answering the questionnaire. Participation was voluntary, and all participants could withdraw from the study at any time. Data were kept confidential and only accessible by the primary investigator, co-investigators, and the statistician; hence, secondary and tertiary blinding was not done. Results Among those who reported PHP, the highest prevalence was among those who did not exercise regularly (94.7%), followed by middle-aged women (64.3%) and those with a high body mass index (44.5%), previous foot problems (43.2%), and chronic medical diseases (41.9%). PHP was less prevalent in male teachers, those with normal body mass index, and those who spent less time standing, had no previous foot problems, and exercised regularly. Most (88.1%) participants with PHP had other musculoskeletal pain, particularly in the lower back (62.6%) and knee (40.1%). Conclusions Teachers can be apprised about the importance of consuming a well-balanced diet and exercising regularly to maintain a healthy weight. We advocate educational programs as they can assist people to understand the need to obtain medical help when they are experiencing pain.