The relationship between a community's services and conditions, satisfaction, and overall quality of life were examined in this study. As these relationships respond to specific contextual and cultural settings, qualitative methods were used to account for their complexity and depth. Key informant interviews were conducted in two rural communities experiencing changes in their living conditions as they shifted to a tourism-driven economy. The study allowed a better understanding of how residents contextualized the abovementioned relationships. Findings suggest the need to account for pre-existing social arrangements, and current community interactional and organizational conditions to better understand resident's perceived living conditions, community satisfaction and quality of life.