Within the fast paced digital transformation of the tourism and hospitality sector, the modalities of booking a tourist accommodation have been radically transformed by the uptake of digital business models and digital platforms. This study examines the underlying mechanisms and key specificities of digital business models for two of the sector’s sub-segments—hotel accommodation bookings and yacht charter accommodation bookings. Based on the literature review findings, the case study method was applied in relation to key digital business models relevant for hotel bookings. On the other end, in relation to the yacht charter segment and its digital business models, an empirical research was conducted, encompassing a final sample of 162 yacht charter agencies from 42 countries worldwide. The analyzed digital business models have multiple similarities, while there are specific differences between the two hospitality segments. Even though digital business models are highly important in both segments, they are generally more developed and sophisticated in the hotel segment, which is related to the segment’s sheer size, in comparison with the younger and smaller yacht charter segment. The novelty is reflected in shedding more light on the characteristics of digital business models in the fast-developing yacht charter segment, including through an empirical study.