Local governments worldwide have been making efforts to regulate Airbnb and its negative externalities (NEs), as peer-to-peer (P2P) accommodations have grown exponentially. This study seeks to explore the perceptions of potential guests regarding the NEs of Airbnb accommodation by using a contextual approach and multiple methodologies to understand the effects of their choice. Through an experiment involving the collection of data on the responses of 296 participants from Taiwan’s post-Millennials and ordered probit model estimations, this study provides a quantitative analysis to distinguish the factors and NEs affecting the likelihood of choosing Airbnb. Under the circumstance where concern for NEs was not included, the results indicated that the accommodation environments and interactive experiences were among the significant Airbnb service features that attracted consumers. However, when NE factors were added a potential effect was identified, with the community environment and security assurances being factors that decreased the likelihood of choosing Airbnb. Previous experiences of staying in hotels were also found to reduce the acceptance of Airbnb as an accommodation mode. These research findings provide insights into Airbnb preferences which could assist in improving the administrative and managerial efforts of P2P accommodation platforms.