Background Many older adults now use technologies such as wearable devices and telehealth services to support their health and well-being while living independently at home. However, older adults vary in how they use these technologies, and there is a lack of knowledge regarding the motivations that influence their acceptance and use of health-related technologies in home environments. Objective This study aimed to understand the types of technologies that older adults use to support their health and the factors that motivate them to use their chosen technologies to support their health. In addition, we aimed to understand the factors that enable the effective use of technologies for health self-management and to identify the barriers that can negatively affect the adoption of technologies. Methods A total of 22 older adults participated in semistructured interviews regarding their experiences of using technologies for health self-management. Interview transcripts were analyzed through an in-depth thematic analysis. Results The interviews revealed that a range of technologies, such as videoconferencing software, fitness trackers, and other devices, were being used by older adults to support their health. Interviews showed that participants were motivated to use technologies to monitor health issues, to stay active and connected, and to record and change their behavior in the light of foreseen risks related to their future health status. Enablers that facilitated the effective use of technologies include social and organizational influence, convenient access to health care and safety provided by the technology, and easy setup and low cost of the technology. Barriers include information overload and a sense of futility about future health decline; telehealth being an inadequate substitute for in-person consultation; concerns about trust related to privacy and accuracy; and technologies being stigmatizing, uncomfortable to use, expensive, and unfamiliar. Conclusions This study suggested that older adults were using a variety of technologies to prevent or prepare for future health decline, evidencing a resilient attitude toward health and aging. In addition, older adults were willing to continue using the technology when there was a perceived need. The enabler mentioned by most participants was the social and organizational influence that included health care staff, family, friends, and organizations. This analysis provides a better understanding of how older adults use technologies to support their health and can guide the provision of appropriate health technologies for them.