We present an efficient approach to ambulance fleet allocation and dynamic redeployment, where the goal is to position an entire fleet of ambulances to base locations to maximize the service level (or utility) of the Emergency Medical Services (EMS) system. We take a simulation-based approach, where the utility of an allocation is measured by directly simulating emergency requests. In both the static and dynamic settings, this modeling approach leads to an exponentially large action space (with respect to the number of ambulances). Futhermore, the utility of any particular allocation can only be measured via a seemingly “black box” simulator. Despite this complexity, we show that embedding our simulator within a simple and efficient greedy allocation algorithm produces good solutions. We derive data-driven performance guarantees which yield small optimality gap. Given its efficiency, we can repeatedly employ this approach in real-time for dynamic repositioning. We conduct simulation experiments based on real usage data of an EMS system from a large Asian city, and demonstrate significant improvement in the system’s service levels using static allocations and redeployment policies discovered by our approach.