Adaptive heritage reuse is a useful method to bring new meaning into a culture, manage heritage sites, and promote tourism development. However, it is not always successful, and there is no theoretical framework to understand its attractiveness and value. This study aimed at developing such a theoretical framework based on the analysis of nine cases of adaptive heritage reuse in Taiwan. The probe question technique of qualitative interview was used to assess the attraction framework. A total of 90 respondents were interviewed based on constant comparative analysis with the sampling strategy of theoretical saturation. The results illustrate the heritage and activities of the reuse environments, including natural and regional environments. These environments produce recreational values, including self-growth, health benefits, and social benefits. As promoting activities is an important attraction for tourists in the heritage reuse environment, the natural environment can be used to plan and design heritage outdoor activities. Finally, the regional environment can be an important basis for assessing the feasibility of adaptive heritage reuse, including historical streets, surrounding tourist attractions, and high transportation accessibility. This theoretical framework can be used to achieve sustainable management of heritage sites.