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The search for luxurious hospitality experiences increasingly coincides with the imperative to mitigate negative impacts in the pursuit of greater sustainability. This is a task often understood as being complex particularly in the context of luxury hospitality which often resonates with conspicuous consumption. This chapter uses a case study approach to analyze the complex relationship between luxury tourism and sustainability. The study focuses on the development of “luxury” from a materialistic perspective toward an experience economy and relates this to the concept of sustainability and agreements relevant to the tourism industry. The environmental impact of luxury hospitality is then discussed. The case study on properties in Costa Rica, South Africa, the Maldives, Vietnam, and French Polynesia focuses on philosophy, facilities, energy and waste consumption, food and beverage, conservational and educational activities, and alignment to the United Nations Sustainable Development Goals (UN SDGs). The focus is on the properties and shows limitations in that it is not applicable to the whole tourist journey and experience. All properties understand luxury as based on experiences and involvement in nature. Measures to mitigate environmental impact and foster conservational and educational activities are mainstream practices. Comparing the cases with academic literature on luxury, sustainability, ecotourism, and environmental policies underline that sustainability-driven luxury hospitality shows valuable steps toward a more sustainable product but is ultimately faced with the dilemma of taking into consideration and ultimately mitigating the impacts of the entire travel value chain.