The decline in children’s interactions with nature has been a great concern in the past few decades. Parents’ orientation toward children’s nature play could strongly influence the extent of children’s interaction with nature, as they are the main decision-makers for young children. To understand the importance of parental orientation (perceived benefits and barriers against children’s nature play and permission for children’s free nature play), we compared the effect of parental orientation with the lack of time and spaces on the frequency of children’s visits to greenspaces (FCG). To measure the influential levels of these factors, we constructed structural equation models using questionnaire data obtained from 516 parents in Japan. We found that the parents’ orientation was the most important driver of FCG across greenspace types and children’s ages, while time constraints did not significantly affect FCG. The effect of the lack of greenspaces was only found to be correlated negatively with children’s farm visits and positively with park visits, while it had no significant effect on children’s visits to forests and rivers. Given the prominent effect of parents’ orientation, our study highlights that improving parental positive perception and permission is key to promoting children’s greenspace use and interaction with nature.