Grasslands are one of the ecosystems that have been strongly affected by anthropogenic impacts. The state-of-the-art in monitoring changes in grassland species composition is to conduct repeated plot-based vegetation surveys that assess the occurrence and cover of plants. These plot-based surveys are typically limited to comparably small areas and the quality of the cover estimates depends strongly on the experience and performance of the surveyors. Here, we investigate the possibility of a semi-automated, image-based method for cover estimates, by analyzing the applicability of very high spatial resolution hyperspectral data to classify grassland species at the level of individuals. This individual-oriented approach is seen as an alternative to community-oriented remote sensing depicting canopy reflectance as the total of mixed species reflectance. An AISA+ imaging spectrometer mounted on a scaffold was used to scan 1m2 grassland plots and assess the impact of four sources of variation on the predicted species cover: (1) the spatial resolution of the scans, (2) complexity, i.e. species number and structural diversity, (3) the species cover and (4) the share of functional types (graminoids and forbs). Classifications were conducted using a support vector machine classification with a linear kernel, obtaining a median Kappa of ~0.8. Species cover estimations reached median r2 and root mean square errors (RMSE) of ~0.6 and ~6.2% respectively. We found that the spatial resolution and diversity level (mainly structural diversity) were the most important sources of variation affecting the performance of the proposed approach. A spatial resolution below 1cm produced relatively good models for estimating species-specific coverages (r2=~0.6; RMSE=~7.5%) while predictions using pixel sizes over that threshold failed in this individual-oriented approach (r2=~0.17; RMSE=~20.7%). Areas with low inter-species overlap were better suited than areas with frequent inter-species overlap. We conclude that the application of very high resolution hyperspectral remote sensing in environments with low structural heterogeneity is suited for individual-oriented mapping of grassland plant species.