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The growing traffic on city streets leads to traffic disruptions, lowering the level of road safety, as well as the problem of finding a vacant parking space. Drivers looking for a vacant parking space on the street generate so-called search traffic. Paid parking zones are introduced to increase the availability of parking spaces for more drivers in many cities around the world. The development in the technology and information sector has contributed to the development of systems guiding drivers to vacant parking spaces. This article aims to analyze drivers' subjective assessment of the ease of finding a vacant parking space in an area equipped with vehicle detection devices. Data from the Municipal Roads Authority in Gliwice (Poland) were obtained for the study, covering the use of parking spaces in the paid parking zone covered by dynamic parking information. Moreover, a survey was conducted among users of the paid parking zone in Gliwice. The answers of the respondents were used to build a logit model that allows determining the probability of a driver's positive subjective assessment of the ease of finding a vacant parking space in an area equipped with vehicle detection devices. The results from the model allow the characterization of drivers who positively assess the ease of finding a vacant parking space in the area equipped with vehicle detection devices. In addition, it is possible to reach a group of drivers who negatively assessed the ease of finding a vacant parking space to learn about the factors that may cause them to change their assessment to a positive one. The research results allow city authorities to better manage parking spaces equipped with vehicle detection devices in the paid parking zone. This may change the negative assessment of the ease of finding a vacant parking space into a positive one.