Background: Dental fear and anxiety (DFA) significantly affect children’s oral health behaviors, cooperation during dental treatment, and long-term dental attendance patterns. Parental DFA may be associated with children’s dental fear through mechanisms such as observational learning, parental communication, and emotional transmission. Methods: A multicenter cross-sectional study was conducted with 296 children aged 7–14 years and their parents attending pediatric dentistry clinics in Eskişehir, Nevşehir, and Malatya, Turkey. Data were collected using questionnaires that included demographic information, parental dental anxiety assessed with Corah’s Dental Anxiety Scale (CDAS), and children’s dental anxiety measured using the Abeer Children’s Dental Anxiety Scale (ACDAS). Statistical analyses included chi-square tests, correlation analyses, and logistic regression models, with significance set at p < 0.05. Results: The prevalence of dental fear and anxiety among children was 59.5%, which may reflect the clinical nature of the sample. In multivariate logistic regression analysis, parental dental anxiety level was significantly associated with children’s dental anxiety (overall p = 0.039). Compared with the reference group, lower parental anxiety levels were associated with reduced odds of child dental anxiety (low anxiety: Odds Ratio (OR) = 0.41, 95% Confidence Interval (CI): 0.19–0.92, p = 0.031; moderate anxiety: OR = 0.41, 95% CI: 0.19–0.90, p = 0.026). Additionally, parental negative dental experience was significantly associated with children’s dental anxiety (OR = 1.81, 95% CI: 1.11–2.95, p = 0.018). Conclusions: Parental dental fear and anxiety are associated with children’s dental anxiety. Family-related factors, particularly parental anxiety and communication patterns, may influence children’s dental fear. Parent-focused interventions and improved communication strategies may help children cope with dental anxiety.