The purpose of this chapter is to reflect on business models employed by online travel service providers since the beginning of online travel until 2019. In lockstep with technological development, this study identified three time periods of development. For each period, we investigate cases that best represent e-business model development. Employing Wirtz’s four business-to-consumer business model subtypes, we found that the commerce-type model (focus on trade transactions) dominated online travel agencies until 2000, while the next period was characterized by the advent of Web 2.0-enabled content-type models (providing online content, specifically user-generated content) and context-type models (aggregation of already existing online content) for information search portals. Finally, the increased complexity of the Internet in the last decade is also captured in multiple online business models, including the connection-type model (establishing real or virtual connections) pursued by platform businesses. The chapter offers avenues for future research that relate to theoretical issues across the three identified periods and an outlook of future tourism business model developments.