Peoples’ recreation and well-being are closely related to their aesthetic enjoyment of the landscape. Ecosystem service (ES) assessments record the aesthetic contributions of landscapes to peoples’ well-being in support of sustainable policy goals. However, the survey methods available to measure these contributions restrict modelling at large scales. As a result, most studies rely on environmental indicator models but these do not incorporate peoples’ actual use of the landscape. Now, social media has emerged as a rich new source of information to understand human-nature interactions while advances in deep learning have enabled large-scale analysis of the imagery uploaded to these platforms. In this study, we test the accuracy of Flickr and deep learning-based models of landscape quality using a crowdsourced survey in Great Britain. We find that this novel modelling approach generates a strong and comparable level of accuracy versus an indicator model and, in combination, captures additional aesthetic information. At the same time, social media provides a direct measure of individuals’ aesthetic enjoyment, a point of view inaccessible to indicator models, as well as a greater independence of the scale of measurement and insights into how peoples’ appreciation of the landscape changes over time. Our results show how social media and deep learning can support significant advances in modelling the aesthetic contributions of ecosystems for ES assessments.