Water stress is a major factor affecting grapevine yield and quality. Standard methods for measuring water stress, such as midday stem water potential (ΨSWP), are laborious and time-consuming for intra-block variability mapping. In this study, we investigate water status variability within a 2.42-ha commercial Cabernet Sauvignon block with a standard vertical trellis system, using remote sensing (RS) tools, specifically canopy fraction-based vegetation indices (VIs) derived from multispectral unmanned aerial vehicle (UAV) imagery, as well as standard reference methods to evaluate soil and plant water status. A total of 31 target vines were monitored for ΨSWP during the whole growing season. The highest variability was at véraison when the highest atmospheric demand occurred. The ΨSWP variability present in the block was contrasted with soil water content (SWC) measurements, showing similar patterns. With spatial and temporal water stress variability confirmed for the block, the relationship between the ΨSWP measured in the field and fraction-based VIs obtained from multispectral UAV data was analysed. Four UAV flights were obtained, and five different VIs were evaluated per target vine across the vineyard. The VI correlation to ΨSWP was further evaluated by comparing VI obtained from canopy fraction (VIcanopy) versus the mean (VImean). It was found that using canopy fraction-based VIs did not significantly improve the correlation with ΨSWP (NDVIcanopyr = 0.57 and NDVImeanr = 0.53), however fractional cover (fcover) did seem to show a similar trend to plant water stress with decreasing canopy size corresponding with water stress classes. A subset of 14 target vines were further evaluated to evaluate if additional parameters (maximum temperature, relative humidity (RH), vapour pressure deficit, SWC and fractional cover) could serve as potential water stress indicators for future mapping. Results showed that the integration of NDVIcanopy and NDREmean with additional information could be used as an indicator for mapping water stress variability within a block.