Osteosarcopenic obesity is a unique clinical condition where low bone and muscle mass coexist in individuals with obesity. Alterations in adipose tissue, skeletal muscle and bone are strictly interconnected, and vitamin D plays key roles in several metabolic pathways that are involved in maintaining musculoskeletal health and glucose homeostasis. We reviewed the available literature on mechanisms underlying osteosarcopenic obesity, with a focus on the role of vitamin D in the pathogenesis and treatment of the condition. We found that, although evidence from large observational studies and pre-clinical experiments strongly supports a role of vitamin D deficiency in the pathogenesis of osteosarcopenic obesity, the common belief that vitamin D improves musculoskeletal health lacks solid clinical evidence, as trials specifically aimed at assessing the effects of vitamin D supplementation in patients with osteosarcopenic obesity are not available, and trials that investigated the role of vitamin D on muscle and bone health in other patient populations either showed no or even detrimental effects. We conclude that large observational and interventional studies including individuals with osteosarcopenic obesity representative of different sex, age and race are needed to better define the role of vitamin D in the pathogenesis and treatment of this condition.