This research concerns the multilayered images and activities of tourism, such as nature experiences and cultural experiences, found on Amami Oshima Island, Kagoshima Prefecture. The expansion of its areas where the accommodations located was noted by observing the relationship between Amami’s tourism image and activities and its accommodations from 1978 to 2018—a timeframe that we divided into four periods. Among the recent accommodations, the small-sized ones account for about 80% of the total. Furthermore, it is possible that small-scale accommodations that are easily adaptable to tourism shifts can provide a “place” that sustains the local culture and tourism.