In this paper, as research problems, it is necessary to examine the readiness of enterprises to invest in the information system, as well as to determine the feasibility of introducing the information system and its most cost-effective financing model. The author wrote in the paper on information systems and organization of boat hire companies to better understand the readers' need to introduce an information system. In addition, the impact of the information system on the company's business results and the most cost-effective financing models were analyzed. The final part of the work gives an insight into the results of the researches as well as the authors' recommendations for implementation. Studies were conducted based on information obtained from the company's reported financial statements, statistical data collected from the interview of several boat rental companies and literature research. The research carried out has shown that the observed company is operating steadily and that it is ready to invest but also that the existing organizational structure has grown. Looking at the results of the research, we conclude that introducing information systems brought long-term savings and benefits to the enterprise. Practice recommendations are certainly the introduction of the information system primarily as a system that will efficiently be able to manage and control costs.