Rural livelihoods are under threat, not only from climate change and soil erosion but also because young people in rural areas are increasingly moving to urbanized areas, seeking employment and education opportunities. In the Valparaiso region of Chile, megadrought, soil degradation, and industrialization are driving young people to leave agricultural and livestock activities. In this study, our main objective was to identify the factors influencing young people living in two rural agricultural communities (Valle Hermoso and La Vega). We conducted 90 online surveys of young people aged 13–24 to evaluate their interest in living in the countryside (ILC). We assessed the effect of community satisfaction, connectedness to nature, and social valuation of rural livelihoods on the ILC. The results show that young people were more likely to stay living in the countryside when they felt satisfied and safe in their community, felt a connection with nature, and were surrounded by people who enjoyed the countryside. These results highlight the relevance of promoting place attachment and the feeling of belonging within the rural community. Chilean rural management and local policies need to focus on rural youth and highlight the opportunities that the countryside provides for them.