In pediatric pharmacotherapy, parents often play a central role in medication management and administration support, and continuous support from community pharmacists is important. However, it remains unclear how continuity of pharmacy use is associated with parent-reported evaluations of pharmacists. This study conducted a web-based survey of 1,788 parents of children younger than 6 years and examined the association between these factors. Parent-reported evaluations of pharmacists were assessed using items adapted based on the Japanese version of the Medical Interview Satisfaction Scale (MISS-21J), with Distress relief, Communication comfort, and Rapport used as evaluation indicators. Multiple linear regression analyses showed that, compared with the usually same pharmacy group, the always same pharmacy group had significantly higher Distress relief and Rapport scores and a significantly lower Communication comfort score. The different pharmacy each time group had a significantly lower Distress relief score than the usually same pharmacy group, whereas no significant differences were observed for Communication comfort or Rapport. These findings suggest that consistent use of the same pharmacy may be associated with parents’ perceived distress relief and rapport with pharmacists. However, the observed differences were small, and their practical and clinical relevance remains uncertain. Further studies are needed to confirm these findings using validated measures and medication-related or clinical outcomes.