The literature dealing with health and entrepreneurship has focused on developed countries. We use a sample of almost 5000 business owners and wage-workers from four Caribbean Basin countries to study this relationship. Analyses are performed using data from the Global Entrepreneurship Monitor along with the Visual Analogue Scale of the EQ-5D-5L instrument as an overall health rating. The results show that business owners are healthier than wage-workers, which is in line with the findings from studies in developed countries. Furthermore, better health is associated with a lower likelihood for fear of business failure to be a deterrent to new business formation, a greater likelihood of self-belief in having the skills to run a business, and an increased recognition of start-up business opportunities among wage-workers. These positive associations between health and entrepreneurial perceptions provide new evidence about why less healthy individuals refrain from entrepreneurship. Finally, we find that the healthiest business owners run the companies with the highest growth expectations.