Background: Inadequate sleep has been shown to have detrimental effects on academic performance, physical, mental, and emotional health among adolescents. Factors that influence sleep have been identified. However, most literature is currently limited to urban settings. This study sought to identify factors that influence sleep habits among high school students in a semi-rural community. Methods: Twelve focus groups were conducted in-person with separate groups of students, parents, and school staff in October 2019. Discussions focused on sleep experiences, knowledge, environment, and factors influencing sleep. Data were coded using grounded theory approach. Themes were identified through summative content analysis. Results: Four major themes were identified: (1) inadequate sleep adversely affects academic performance and emotional health; (2) students face a gap in knowledge regarding sleep duration; (3) academic and nonacademic activities compete with sleep needs; and (4) night-time use of technology negatively influences sleep habits. Conclusions: Our findings suggest that high school students do not get adequate sleep, largely due to the demands of academic and extracurricular activities and the use of electronics at night. These results can guide the development of targeted sleep education and intervention programs.