A vehicle surrounding area imaging system is configured to allow a driver to easily view and verify an image surrounding a peripheral side of the vehicle. The vehicle surrounding area imaging system basically has two cameras, a navigation system, a startup imaging determination unit and a monitor. The cameras take images of the areas to the sides of the vehicle to acquire images. The navigation system detects the current position of the vehicle. The startup imaging determination unit detects predetermined road regions that requires an image to be displayed from the periphery around the vehicle based on the current position detected by the navigation system as well as map information. The monitor selectively displays the images acquired by the cameras before the vehicle enters into one of the predetermined road region that requires an image display.