Finding a parking space in urban areas is a daily challenge for drivers across the world, due to the increasing amount of vehicles and the limited amount of parking spaces. Drivers who are looking for a parking space in peak hours are often forced to drive around city blocks until they spot a free parking space. This process is termed in literature "cruising for parking" and is proven to (a) cost a lot of time and gas for drivers, (b) generate unnecessary traffic load, and (c) affect the environment negatively due to increased vehicle emissions. This work proposes a Parking Monitoring and Management System (PMMS) that collects, processes, and presents data about available parking spaces and their tariffs within a geographical region. The end-user application of the PMMS, parkITsmart, delivers at drivers bird's-eye view concerning the parking availability. To facilitate this, the PMMS gathers data from drivers', vehicles, their mobile phones, and Parking Inspectors (PIs). This work shows that in the Internet-of-Things (IoT) environment, "pairing" cars and drivers' mobile phones, collecting data from their sensors, and from PIs in a parking monitoring and management system, can decrease significantly cruising times for parking and can increase the time demands of the parking controlling process.