With the globalizing trends, innovative approaches have stood out in the tourism sector. In line with these approaches, the number of entrepreneurships in tourism increases and a significant association is formed between tourism and entrepreneurship in terms of sustainability. Tourism activities, which have an important role in regional development, can make significant contributions to the economy of the region with the entrepreneurship activities carried out by the local people. This study sets forth the relationship between tourism and entrepreneurship in ensuring sustainable tourism development in the tourism destination of Amasya, which is rich in historical areas, cultural and natural features, based on small-scale enterprises. The study covers identification of key success factors affecting tourism entrepreneurship and testing of the relationship between the factors and performance via the SPSS program (Statistical Package for the Social Sciences) by conducting a survey that measures subjective and objective perception with 78 small-scale tourism enterprises. As the result of the study, it has been concluded that environmental, organizational, enterprise-oriented and entrepreneur-oriented features should be discussed in a holistic manner in the development of sustainable tourism entrepreneurship.