Abstract: A system and method for completing an automated online transaction related to vacation rental property between an owner and a prospective rentor. Owners of vacation rental property provide information in the form of a Listing to an owner database at a website which provides access to the owner database by prospective rentors. Rentors can then select a desired Listing and book the associated property online and in real-time. Each Listing includes a rental schedule associated with a particular vacation rental home, a contract for the rentor to complete, and an application form. The website provides an interface comprising a field for the rentor to view and select at least one of the Listings and to provide personal information via the application form. A booking engine processes the completed application form, verifies that the rentor has agreed to the terms and conditions of the contract, generates an instant approval for a qualified rentor, and executes a booking with the qualified rentor.