Digital technologies, including peer-to-peer platforms and online booking systems, have significantly transformed the tourism industry, with short-term rental accommodations (STRA) becoming a key component of global options. While STRA has notably impacted urban tourist centres, its effects on rural sustainability are less explored. This chapter examines STRA, or ‘alojamento local' (AL) in Portugal, in the rural Algarve, comparing its impacts to urban settings. Using both secondary quantitative data from national databases and qualitative interviews with stakeholders, this study aims to expand the limited literature on rural STRA. It characterizes rural AL patterns, explores the connections between lifestyle migrant entrepreneurship and the STRA sector, and assesses their role in sustainable rural development. This research also addresses the challenges and opportunities in promoting rural tourism as a driver for a sustainable future in areas considered ‘lagging' and ‘in decline' for decades.