Fully automated provisioning and deployment in order to reduce the costs for managing applications is one of the most essential requirements to make use of the benefits of Cloud computing. Several approaches and tools are available to automate the involved processes. The DevOps community, for example, provides tooling and artifacts to realize deployment automation on Infrastructure as a Service level in a mostly application-oriented manner. Platform as a Service frameworks are also available for the same purpose. In this paper we categorize and characterize available deployment approaches independently from the underlying technology used. For this purpose, we choose Web applications with different technology stacks and analyze their specific deployment requirements. Afterwards, we provision these applications using each of the identified types of deployment approaches in the Cloud. Finally, we discuss the evaluation results and derive recommendations which deployment approach to use based on the deployment requirements of an application.