Interactions between land and atmosphere directly influence hydrometeorological processes and, therefore, the local climate. However, because of heterogeneity of vegetation covers these feedbacks can change over small areas, becoming more complex. This study aims to define how the interactions between soil moisture and vegetation covers influence soil temperatures in very water-limited environments. In order to do that, soil water content and soil temperature were continuously monitored with a frequency of 30 min over two and half hydrological years, using capacitance and temperature sensors that were located in open grasslands and below tree canopies. The study was carried out on three study areas located in drylands of Mediterranean climate. Results highlighted the importance of soil moisture and vegetation cover in modifying soil temperatures. During daytime and with low soil moisture conditions, daily maximum soil temperatures were, on average, 7.1 °C lower below tree canopies than in the air, whereas they were 4.2 °C higher in grasslands than in the air. As soil wetness decreased, soil temperature increased, although this effect was significantly weaker below tree canopies than in grasslands. Both high soil water content and the effect of shading were reflected in a decrease of maximum soil temperatures and of their daily amplitudes. Statistical analysis emphasized the influence of soil temperature on soil water reduction, regardless of vegetation cover. If soil moisture deficits become more frequent due to climate change, variations in soil temperature could increase, affecting hydrometeorological processes and local climate.