Longer term monitoring of soil water content at a catchment scale is a key to understanding its dynamics, which can assist stakeholders in decision making processes, such as land use change or irrigation programs. Soil water monitoring in agriculturally dominated catchments can help in developing soil water retention measurements, for assessment of land use change, or adaptation of specific land management systems to climate change. The present study was carried out in the Pannonian region (Upper-Balaton, Hungary) on Cambisols and Calcisols between 2015 and 2021. Soil water content (SWC) dynamics were investigated under different land use types (vineyard, grassland, and forest) at three depths (15, 40, and 70 cm). The meteorological data show a continuous decrease in cumulative precipitation over time during the study with an average of 26% decrease observed between 2016 and 2020, while average air temperatures were similar for all the studied years. Corresponding to the lower precipitation amounts, a clear decrease in the average SWC was observed at all the land use sites, with 13.4%, 37.7%, and 29.3% lower average SWC for the grassland, forest, and vineyard sites, respectively, from 2016 to 2020 (measured at the 15 cm depth of the soil). Significant differences in SWC were observed between the annual and seasonal numbers within a given land use (p < 0.05). The lowest average SWC was observed at the grassland (11.7%) and the highest at the vineyard (28.3%). The data showed an increasing average soil temperature, with an average 6.3% higher value in 2020 compared to 2016. The grassland showed the highest (11.3 °C) and the forest soil the lowest (9.7 °C) average soil temperatures during the monitoring period. The grassland had the highest number of days with the SWC below the wilting point, while the forest had the highest number of days with the SWC optimal for the plants.