Road accidents remain a serious problem and directly affect drivers. Therefore, the perspectives of drivers are important in improving road safety. The objectives of this study are to empirically examine damage due to road accidents using the willingness-to-pay (WTP) approach and to analyze the factors that influence WTP at the driver and district levels. This study obtained data on WTP derived from car drivers across Thailand, which covers 96 districts. The value of statistical life was 824,344 USD per fatality (2,296 million USD annually). The results of Multilevel Structural Equation Modeling revealed a statistically important insight. At the driver level, the Health Belief Model and sociodemographic exert influence on the intention to pay. The demographic factor that has the greatest influence on perceived risk and leads to a high intention to pay is the working age group (γ = 0.826). However, when considering the HBM, perceived susceptibility (γ = 0.901) emerges as the most valuable factor influencing drivers’ concerns about road accidents. On the other hand, district-level factors have a negative influence on the intention to pay for road safety measures. Among these factors, the law enforcement (γ = −0.555) practices implemented by local authorities have the most significant impact on drivers’ perspectives and intentions regarding WTP. This finding can be used as a guideline for budget allocation and policy recommendation for policymakers in improving road safety according to the area contexts.