Abstract: The development of rural non-agricultural entrepreneurship not only improves rural household income and living standards, but also promotes the allocation and utilization of land resources, which has an impact on farmland transfer. Based on the data of China Household Finance Survey (CHFS) in 2015, this paper analyzed the impact of household’s non-agricultural entrepreneurship on farmland transfer-out by the Probit model and the Tobit model and further discussed the intermediary role of family insurance programs by constructing an intermediary effect model. Research results show that the proportion of non-agricultural entrepreneurship is 14.6%, not very high, and the participation rates of farmland transfer-out behavior and the average proportion of transfer-out scale are 17.4% and 14.4% respectively, at relatively low levels. Non-agricultural entrepreneurship has a significant role in promoting farmers’ farmland transfer-out behavior and scale. In addition, the analysis of heterogeneity shows that the impact intensity of non-agricultural entrepreneurship of young farmers is significantly higher than that of elderly farmers. Furthermore, non-agricultural entrepreneurship further promotes farmers’ farmland transfer-out behavior and scale by promoting their family participation in insurance programs. Family insurance participation plays a partial mediating role in the process of the impact of non-agricultural entrepreneurship on farmland transfer-out. Therefore, this paper suggests: to promote the transfer of agricultural labor force to non-agricultural work, to implement differentiated policy support and employment guidance based on the development characteristics of farmers and to improve farmers’ insurance participation rate by optimizing the rural security system.