In the digital era, more and more people tend to look for travel-related information on the Internet. Hence, destination marketing organization (DMO) websites can play a decisive role in affecting people’s destination choices. Based on the study of Pai, Xia, and Wang, Macao’s DMO website received the lowest score in the effectiveness when compared to the other four tourism destinations: Japan, Korea, Hong Kong, and Thailand. This paper aimed to carry out a comparative analysis on the functionality among three DMO websites in Asia. Each website was examined in great detail, and the features were categorized according to a well-established conceptual framework pioneered by Li and Wang. Consequently, the results of this study gave useful information and new insights to destination marketing managers in terms of gap analysis and the development of new features for their websites. The results of this research could be used as benchmarking purposes in regards to website functionality. In addition, DMO websites in western countries, such as Canada, were also examined for a better understanding of the comprehensiveness of the available website functionality aimed for prospective visitors. Business and managerial implications were also discussed.