In a monitoring system for monitoring parking of a vehicle in a specific area by a monitoring image pick-up device, and a monitoring apparatus, the monitoring image pick-up device includes an image pick-up portion. And the monitoring apparatus includes: a parking area enter/exit determining portion for determining whether or not a vehicle enters or exits from the specific area; an imaging setting change instructing portion for instructing the image pick-up portion to change an imaging setting to another one suitable for capturing a vehicle image containing specific information on the vehicle when it is determined that the vehicle enters or exits from the area; and a parking determining portion for calculating a time for which the vehicle is parked in the area from image capturing time when the vehicle enters the area, and image capturing time when the vehicle exits from the area.