Drought is one of the most damaging environmental hazards and a naturally occurring phenomenon in Central Asia that is accompanied by crucial consequences for the agriculture sector. This research aimed at understanding the nature and extent of drought over the cropland regions of Central Asia with the help of spatiotemporal information from the region. We assessed drought occurrence using the vegetation health index (VHI). An algorithm was developed to reduce the noise of heterogeneous land surfaces by adjusting the vegetation index and brightness temperature. The vegetation condition index (VCI) and temperature condition index (TCI) were calculated using Moderate Resolution Imaging Spectroradiometer (MODIS) products for the growing season (April–September) from 2000 to 2015. The intense drought years were identified and a drought map (drought probability occurrence) was generated. The findings of this research indicated regional heterogeneity in the cropland areas having experienced droughts, observed through spatiotemporal variations. Some of the rain-fed and irrigated croplands of Kazakhstan demonstrated a higher vulnerability to annual drought occurrences and climate change impacts, while other cropland regions were found to be more resistant to such changes. The development of policy tools is required to support informed decision-making and planning processes to adapt to the occurrence of droughts. This could be achieved by the timely assessment, monitoring, and evaluation of the spatiotemporal distribution trends and variabilities of drought occurrences in this region. The results from this study focus on the spatiotemporal variations in drought to reveal the bigger picture in order to better understand the regional capacity for sustainable land management and agricultural activities within a changing environment.