The study aims to investigate the perceptions of the UAE digital natives regarding web vendors, and online privacy and security, that in turn determine their online shopping intentions. Despite exponential growth in e-commerce in the GCC in general and UAE in particular, and favorable economic and demographic factors, research in this realm is sparse. This study attempts to fill this void. More than 200 respondents aged between 18-30 years are surveyed and data is collected on their perceptions regarding various characteristics of web vendors, online security and privacy, and online shopping intentions. Principal Component Analysis and Binary Logistic Regression is used for dimension reduction and to examine association between the extracted factors and intention to shop online for the target group, respectively. The results highlight the importance of establishing positive brand image and adapting effective and viable privacy protection mechanisms to motivate consumers to shop online and use payment mechanisms other than cash on delivery.