Disclosed is an employee vacation scheduling system for enabling an employee to purchase vacation travel services on the basis of the availability of the paid leaves thereof. The vacation scheduling system comprises a database comprising a plurality of employees wherein, each employee is associated with the number of paid leaves the employee is entitled to. The scheduling system further comprises a store module for enabling an employee to purchase a vacation travel service that spans a predetermined number of vacation days, a date module for enabling the employee, in the process of purchasing the vacation travel service, to mark successive vacation dates for the utilization of the vacation travel service, and a payment module for enabling the employee to pay for the vacation travel service upon determining that the number of vacation days are lesser than or equivalent.