This article aims to provide an accurate mathematical model with the minimum number of degrees of freedom for describing the floating sleeper phenomenon. This was accomplished using mathematical modeling supported by extensive field measurements of the railway track. Although the observed phenomenon is very complex, the simplified single degree of freedom (SDOF) mathematical model proved accurate enough for its characterization. The progression of the deterioration of the railway track was successfully correlated to changes in the maximal dynamic factor for different types of pulse loading. The results of the presented study might enable the enhanced construction and maintenance of railroads, particularly in karst areas.