The advent of the Internet envisions a cashless society by enabling financial transactions through digital payments. Significantly, the emergence of coronavirus (COVID-19) disrupted our traditional cash handling means and triggered an inflexion point for switching towards contactless digital payments from physical cash payments. Furthermore, Internet of Things (IoT) technology escalates digital payments to the next level by enabling devices to render goods and services without requiring any human interaction. This research proposed an IoT-enabled cashless vending machine that incorporates both cloud computing and payment gateway for ordering and purchasing items through digital payment systems by using a mobile application. The system enables a pre-installed mobile application to scan the Quick Response (QR) code attached to the body of a vending machine, opens the portal of a webbased virtual machine through the code, allows user to choose and order items from the virtual vending, initiates and authorizes a digital payment through an IoT gateway installed inside the physical vending machine by establishing a connection between user's and vendor's financial entities, and finally, dispenses the ordered items by unlocking the shelves of the vending machine after the successful payment transaction. It operates in the Arduino platform with an ATmega 2560 Microcontroller and Esp8266 Wi-fi module as hardware components, mobile application software, and payment gateway API. The system performed an average response time of 14500 milliseconds to pick a product after running 150 consecutive API test calls. This result shows a satisfying time for enhancing customers' buying experiences with digital payment systems and a customizable and cost-effective IoT-based intelligent vending machine to introduce for mass production.