A plethora of research has been conducted over the past few years to explore several aspects of the key exchange actors within the sharing accommodation sector (i.e. hosts and guests). However, despite the exponential growth in the sharing accommodation entrepreneurship, literature exploring the characteristics, motivations, and challenges of entrepreneurs venturing in this sector is still scant. This study draws on a qualitative study approach using semi-structured interviews with entrepreneurs involved in the sharing accommodation sector in Petra, Jordan. Findings revealed that sharing accommodation entrepreneurs were mainly driven by the desire for economic and cultural benefits. The positive host-guest relationship (e.g., honesty toward guests and enhancing positive reputation) emerged as a key factor influencing the growth of the sharing accommodation businesses whereas market-related issues (e.g., severe competition and lobbying efforts from traditional lodging businesses) were found to be the key challenges derailing the businesses.