The Loess Plateau is an important grain-producing area and energy base in China and is an area featuring dramatic changes in both surface and underground processes. However, the associations between surface deformation and groundwater storage changes in different landscape types in the region are still unclear. Based on Sentinel-1 and GRACE (Gravity Recovery and Climate Experiment) data, this study monitored and verified the surface deformation and groundwater storage changes in different landscape types, such as those of the Kubuqi Desert, Hetao Irrigation District, Jinbei Mining Area, and Shendong Mining Area, in the Loess Plateau of China from 2020 to 2021. Through time series and cumulative analysis using the same spatial and temporal resolution, the associations between these two changes in different regions are discussed. The results show that: (1) the surface deformation rates in different landscape types differ significantly. The minimum surface deformation rate in the Kubuqi Desert is −5~5 mm/yr, while the surface deformation rates in the Hetao Irrigation District, the open-pit mine recovery area in the Jinbei Mining Area, and the Shendong Mining Area are −60~25 mm/yr, −25~25 mm/yr, and −95.33~26 mm/yr, respectively. (2) The regional groundwater reserves all showed a decreasing trend, with the Kubuqi Desert, Hetao Irrigation District, Jinbei Mining Area, and Shendong Mining Area declining by 359.42 mm, 103.30 mm, 45.60 mm, and 691.72 mm, respectively. (3) The surface elasticity deformation had the same trend as the temporal fluctuation in groundwater storage, and the diversion activity was the main reason why the temporal surface deformation in the Hetao Irrigation District lagged behind the change in groundwater storage by 1~2 months. The measure of “underground water reservoirs in coal mines” slows down the rate of collapse of coal mine roof formations, resulting in the strongest time-series correlation between mild deformation of the surface of the Shendong mine and changes in the amount of groundwater reserves (R = 0.73). This study analyzes the associations between surface deformation and groundwater storage changes in different landscape areas of the Loess Plateau of China and provides new approaches to analyzing the dynamic associations between the two and the causes of changes in both variables.