The northeast of Thailand is well-known as a popular destination where many male Westerners marry Thai women and settle down there. However, little is known about their health and well-being. This study aims to explore the Western husbands’ health status and identify barriers hindering their healthcare access. A qualitative case study was conducted from November 2020 to May 2021. In-depth interviews and focus group discussions with 42 key informants who were involved with social and health issues among these expatriates were carried out. The social determinants framework was adapted for guiding the interviews. Data were triangulated with field notes, document reviews, and researchers’ observations. Inductive thematic analysis was applied. Results showed that most male expatriates who married Thai women in the northeast were in their retirement years and had non-communicable diseases, health risk behaviors, and mental health problems. Most of them did not purchase health insurance and held negative impressions toward Thai public hospitals’ quality of care, which was denoted as the main barrier to accessing healthcare services. Other significant barriers consisted of high treatment costs commonly charged by private hospitals and language issues. While the improvement of healthcare quality and the provision of friendly health services are important, public communication with foreign residents, especially male expatriates, is recommended to increase understanding and improve perceptions of the Thai healthcare systems. A regular population-based survey on the health and well-being of expatriates in Thailand, a cost study of a health insurance package, a survey study on willingness to pay for health insurance premiums, and a feasibility survey exploring the opportunity to establish either voluntary or compulsory health insurance among this group should be undertaken.