Supplement users have better vitamin D status, and parenting is key to promoting a child’s healthy behaviours. We examined the association of parental encouragement of and caring about healthy lifestyles with children’s use of vitamin D supplements and multivitamins. A provincially representative sample of grade 5 students (n = 2686; 10–11 years) and their parents across the province of Alberta, Canada, was surveyed in 2014. Students were asked about use of multivitamins and/or vitamin D supplements. Parents were asked whether they cared about and encouraged healthy lifestyles. Mixed effect multiple logistic regression identified the association of parental responses with children’s use of supplements; 29% and 54% of children took vitamin D supplements and multivitamins, respectively. They were more likely to take vitamin D supplements if their parents cared ‘very much’ vs. ‘not at all/a little bit’ about eating healthy foods (OR = 1.43; 95% CI = 1.08, 1.89), cared ‘quite a lot’ (OR = 1.55; 95% CI = 1.17, 2.04) and ‘very much’ (OR = 1.67; 95% CI = 1.26, 2.21) vs. ‘not at all/a little bit’ about physical activity, and encouraged ‘very much’ vs. ‘not at all/a little bit’ their children to eat healthy foods (OR = 1.51; 95% CI = 1.05, 2.17). Children whose parents personally cared for eating healthy foods were more likely to take multivitamins (‘quite a lot’ and ‘very much’ compared to ‘not at all/a little bit’ (OR = 1.60; 95% CI = 1.13, 2.28 and OR = 1.46; 95% CI = 1.04, 2.06, respectively). Education and parental encouragement of healthy lifestyles should be part of the public health initiatives to promote supplementation of vitamin D among children.