The Canary Islands are one of the main destinations for mass tourism in the European context, characterized by the absence of seasonality in tourist activity. Moreover, the level of activity increases during the winters, coinciding with a greater probability of extreme rainfall events, whose danger seems to be increasing as a result of climate change. Owing to its pronounced orography, the southern coast of the island of Gran Canaria houses several tourist settlements built along ravines and steeply sloping terrain. This scenario presents considerable risk because of spatial probability of landslide occurrence. The case of San Agustín, especially, serves to test the model of tourist urbanization along the hillside, demonstrating its high fragility in the face of extreme rainfall events. Especially owing to its importance in providing assistance in emergency situations, its vulnerability has been analyzed with regard to accessibility, which is entirely dependent on road mobility. The growth model of San Agustín serves as an example of mass tourism in small islands, allowing urban planners and designers to assess corrective measures based on managing its existing road infrastructure and open spaces right from the planning stage.