A key parameter for the design of soil drainage and irrigation facilities and for the modelling of surface runoff and erosion phenomena in land-formed areas is the saturated hydraulic conductivity (Ks). There are many methods for determining its value. In situ and laboratory measurements are commonly regarded as the most accurate and direct methods; however, they are costly and time-consuming. Alternatives can be found in the increasingly popular models of pedotransfer functions (PTFs), which can be used for rapid determination of soil hydrophysical parameters. This study presents an analysis of the Ks values obtained from in situ measurements conducted using a double-ring infiltrometer (DRI). The measurements were conducted using a laboratory permeability meter (LPM) and were estimated using five PTFs in the Rosetta program, based on easily accessible input data, i.e., the soil type, content of various grain sizes in %, density, and water content at 2.5 and 4.2 pF, respectively. The degrees of matching between the results from the PTF models and the values obtained from the in situ and laboratory measurements were investigated based on the root-mean-square deviation (RMSD), Nash–Sutcliffe efficiency (NSE), and determination coefficient (R2). The statistical relationships between the tested variables tested were confirmed using Spearman’s rank correlation coefficient (rho). Data analysis showed that in situ measurements of Ks were only significantly correlated with the laboratory tests conducted on intact samples; the values obtained in situ were much higher. The high sensitivity of Ks to biotic and abiotic factors, especially in the upper soil horizons, did not allow for a satisfactory match between the values from the in situ measurements and those obtained from the PTFs. In contrast, the laboratory measurements, showed a significant correlation with the Ks values, as estimated by the models PTF-2 to PTF-5; the best match was found for PTF-2.