Description: Accurate and up-to-date mapping and monitoring of rubber plantations is challenging. In this study, we presented a simple method for rapidly and accurately mapping rubber plantations in the Xishuangbanna region of southwest China using phenology-based vegetation index differencing. Temporal profiles of the Normalized Difference Vegetation Index (NDVI), Enhanced Vegetation Index (EVI), Atmospherically Resistant Vegetation Index (ARVI), Normalized Difference Moisture Index (NDMI), and Tasselled Cap Greenness (TCG) for rubber trees, natural forests and croplands were constructed using 11 Landsat 8 OLI images acquired within one year. These vegetation index time series accurately demonstrated the unique seasonal phenological dynamics of rubber trees. Two distinct phenological phases (i.e., defoliation and foliation) of rubber trees were clearly distinguishable from natural forests and croplands. Rubber trees undergo a brief defoliation-foliation process between late December and mid-March. Therefore, vegetation index differencing between the nearly complete defoliation (leaf-off) and full foliation (leaf flushing) phases was used to delineate rubber plantations within fragmented tropical mountainous landscapes. The method presented herein greatly improved rubber plantation classification accuracy. Overall classification accuracies derived from the differences of the five vegetation indices varied from 92% to 96% with corresponding kappa coefficients of 0.84–0.92. These results demonstrate the promising potential of phenology-based vegetation index differencing for mapping and monitoring rubber expansion at the regional scale.