Groundwater has become a major source of irrigation in the past few decades in India, but as it comes from millions of individual borewells owned by smallholders irrigating small fields, it is difficult to quantify the actual irrigated area across seasons and years. This study’s main goal was to monitor seasonal irrigated cropland using multiple optical satellite images. The proposed research was performed over the Berambadi watershed, an experimental site in southern peninsular India. While cloud cover during crop growth is the greatest obstacle to optical remote sensing in tropical regions, the cloud-free images from multiple optical satellite platforms (Landsat-8 (OLI), EO1 (ALI), IRS-P6 (LISS3 and LISS4), and Spot5Take5 (HRG2)) were used to fill data gaps during crop growth periods. The seasonal cumulative normalized difference vegetation index (NDVI) was calculated and resampled at 5 m spatial resolution for various cropping seasons. The support vector machine (SVM) classification was applied to seasonal cumulative NDVI images for irrigated cropland area classification. Validation of the classified irrigated cropland was performed by calculating kappa coefficients for three cropping seasons (summer, kharif, and rabi) from 2014–2016 using ground observations. Kappa coefficients ranged from 0.81–0.96 for 2014–2015 and 0.62–0.89 for 2015–2016, except for summer 2016, when it was 1.00. Groundwater irrigation in the watershed ranged from 4.6% to 16.5% of total cropland during these cropping seasons. These results showed that multi-source optical satellite data are relevant for quantifying areas under groundwater irrigation in tropical regions.