Historical droughts in the Western Cape Province of South Africa (WCPSA) have caused severe agricultural losses and water shortages, highlighting the need for systematic vegetation monitoring. This study assesses geospatial trends in vegetation cover and health from 2001—2020 by deriving annual NDVI (Normalized Differential Vegetation Index), VCI (Vegetation Condition Index), and TCI (Temperature Condition Index) from MODIS (Moderate-resolution Imaging Spectroradiometer (MODIS) MOD13A3 monthly vegetation index and MOD11A2 eight-day LST (Land Surface Temperature) composites at a 1 km resolution. Data processing followed standard protocols to compute yearly averages and generate geospatial coverage maps. The results indicate a gradual increase in the annual NDVI, with coastal areas consistently exhibiting greater greenness; the driest periods (2001 and 2011–2013) correspond to pronounced NDVI minima. The TCI values remained largely within the no-drought class (40–100) across all years, reflecting limited temperature-driven stress, particularly in the northern and northeastern zones. In contrast, the VCI displayed greater variability: severe to extreme drought conditions were recorded in 2001, 2003–2004, 2006, and 2011, whereas most intervening years fell within the no-drought thresholds. These divergent trends underscore the complex interplay among precipitation, temperature, and vegetation dynamics in the WCPSA. By revealing spatially explicit patterns of vegetation response, this study can inform targeted agricultural management, irrigation planning, and land-use policy in the Western Cape. Future work should integrate soil moisture and additional climatic indices to enhance drought early warning systems. These findings offer valuable insights for sustainable water and land management locally and in other semiarid regions worldwide.