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<i>Background and Objectives:</i> The controversy about the impact of vitamin D supplementation on weight loss treatment was observed in several randomized controlled trials (RCTs). This meta-analysis investigates the effects of vitamin D supplementation (cholecalciferol or ergocalciferol) on weight loss through holistic measurements of Body Mass Index (BMI), weight and waist circumference. <i>Materials and Methods:</i> Google Scholar, WOS, PubMed and Scopus were explored to collect relevant studies. The selected articles focused on vitamin D supplementation in overweight and obese individuals with different conditions. Eleven RCTs were included into this meta-analysis with a total of 947 subjects, with a mean of the follow-up from 1 to 12 months and different vitamin D interventions (from 25,000 to 600,000 IU/monthly of cholecalciferol). <i>Results:</i> The meta-analyzed mean differences for random effects showed that cholecalciferol supplementation deceases the BMI by &#8722;0.32 kg/m² (CI95% &#8722;0.52, &#8722;0.12 kg/m², <i>p</i> = 0.002) and the waist circumference by &#8722;1.42 cm (CI95% &#8722;2.41, &#8722;0.42 cm, <i>p</i> = 0.005), but does not statistically affect weight loss &#8722;0.43 kg (CI95% &#8722;1.05, +0.19 kg, <i>p</i> = 0.17). <i>Conclusions:</i> This meta-analysis lays the foundation for defining the potential clinical efficacy of vitamin D supplementation as a potential therapeutic option for weight loss programs, but further studies are needed to confirm the validity of these findings and delineate potential underlying mechanisms.