This study compared differences in degree of happiness, social support, activities performed, and health and economic situation among retirees from urban and rural areas in Minas Gerais State in Brazil. The influences of these predictors over individuals' level of happiness were also analyzed. We included 279 retired individuals living in Abre Campo (a municipality with a population fewer than 20,000 inhabitants, which is considered a rural area) and in Belo Horizonte (a municipality with a population of almost 2.5 million inhabitants, which is considered an urban area). Participants responded to a questionnaire that included scales of happiness, social support, diversity of activities, and issues about satisfaction with health and economic situation. Retirees from the urban area had a higher happiness level than retirees from the rural area (β = 0.16). The most important predictors of happiness were health (β = 0.42), social support (β = 0.26), and economic situation (β = 0.15), but no moderation effects of urban and rural areas were found. Our findings support the implementation of actions to offer financial planning before retirement and to stimulate social support and health promotion for retirees, particularly given the importance of these factors in perception of happiness.