With the continuous and rapid rise of urbanization in China, land use transition research has been carried out extensively. Multiple cropping is the content of land use recessive morphology research, and it is also a common agricultural system in China. Accordingly, further research on multiple cropping index (MCI) can enrich the land use transition research and help to evaluate China’s food security. In order to examine the spatiotemporal changes and factors influencing the MCI of cultivated land in China, we collected MODIS remote sensing image data and land use classification data and conducted a remote sensing inversion on China’s MCI from 2000, 2005, 2010, and 2015. The spatial distributions and evolution processes of the MCI were explored through spatial mapping, statistical analysis, and processing with the Geographic Information System; moreover, the influencing factors of MCI were explored quantitatively with principal component regression. The results were as follows: (1) at the provincial scale, the average MCI across Guangdong, Guangxi, Hainan, Henan, Anhui, and Jiangsu was high; meanwhile, the average MCI across Heilongjiang, Inner Mongolia, Ningxia, and Qinghai was low. Between 2000 and 2015, the number of provinces with low MCI increased gradually, and the average MCI decreased greatly in the southern provinces. (2) At the county scale, the Taihang Mountains, Qinling Mountains, and Hengduan Mountains formed the boundary of China’s single cropping and multiple cropping indices. Dynamic changes in China’s MCI were obvious, and the number of counties with MCI change values lower than 0 increased gradually. Last, (3) natural conditions, nonagricultural process, cultivated land quality, and agricultural intensification demonstrated different degrees of impact on the MCI; in particular, the influence of nonagricultural industries, pesticides, and agricultural plastic film on the MCI proved especially important. Future research should strengthen the existing work on related transformations in farmers’ livelihoods, especially in terms of the return of rural labor force, the body of agricultural production, agricultural ecological issues, and the balance between increased crop production and reduced environmental pollution. In addition, agricultural policy design should pay more attention to cultivated land quality, the farmer who cultivates the land, and the multiple cropping potential of cultivated land.