We use two historical case studies (UK and Costa Rica) to explore the antecedents and legitimization of sustainable development in hospitality and tourism, demonstrating the value of historical analysis through careful consideration of motivations, context, and development type under different circumstances. Design: Utilizing government and private archival materials, oral history testimonies, industry reports and secondary literature, we deploy careful historical analysis of developing and developed country approaches to two cases of hospitality and tourism development and how this impacts on notions of sustainability. Findings: Issues surrounding sustainability in hospitality and tourism are longstanding and impacted by their situated context. In considering 'bottom-up' and 'top-down' approaches, this study finds that the private-sector is critical in legitimizing tourism and hospitality development through addressing sustainability aims. Research Implications: Issues faced in developing hospitality and tourism markets should not be taken in isolation and, by drawing upon historical cases, scholars can better-understand how developed tourism markets shape the sustainability of developing contexts.