In China, the transfer of land management rights has always been a topic of much discussion, as it plays an important role in improving land use efficiency, achieving the optimal allocation of agricultural resources, and protecting farmers’ rights and interests. With the advent of an aging society, elderly farmers are becoming the main force of agricultural production, and their land transfer behavior influences the land transfer situation in China. Based on three-period panel data from the China Health and Retirement Longitudinal Survey (CHARLS), this study uses a binary linear regression model to explore the effects of social security, intergenerational care, and their interactions with elderly farmers’ cultivated land renting out behavior. The results show variability among elderly farmers across different regions of China, as well as a variability in other characteristics that influence cultivated land renting out behavior. It was found that: (1) pension insurance had a significant positive effect on elderly farmers’ cultivated land renting out behavior, while the effect of medical insurance was not significant. Elderly farmers who participated/received pension insurance were 4.3% more likely to choose to rent out farmland, compared to those who did not do so. (2) The frequency of intergenerational care had a significant negative effect on elderly farmers’ cultivated land renting out behavior, while the intensity of intergenerational care had no significant effect. (3) There was an interaction between the frequency of intergenerational care and social security, whereby a high frequency of intergenerational care was found to increase the probability of renting out farmland among elderly farmers with pension insurance.