Among the most relevant fields of research recently investigated for improving the performance of gasoline direct injection (GDI) engines, there are ultrahigh injection pressures and the flash-boiling phenomenon. Both perform relevant roles in improving the air/fuel mixing process, reducing tailpipe emissions and implementing new combustion methods. When a high-temperature fuel is released into an environment with a pressure lower than the fuel’s saturation pressure, flash boiling occurs. Due to complex two-phase flow dynamics and quick droplet vaporization, flash boiling can significantly modify spray formation. Specifically, if properly controlled, flash boiling produces important benefits for the fuel–air mixture formation, the combustion quality and, in general, for overall engine operation. Flash boiling was broadly investigated for classical injection pressure, but few works concern ultrahigh injection pressure. Here, the investigation of the spray produced by a multihole injector was performed using both experimental imaging techniques and CFD simulations aiming to highlight the combined impact of the injection pressure and the flash boiling occurrence on the spray morphology. The shadowgraph method was employed to observe the spray experimentally. The information gathered allows for assessing the performances of an Eulerian–Lagrangian algorithm purposely developed. Breakup and evaporation models, appropriate for flashing sprays, were implemented in a CFD (Computational Fluid Dynamics) code. The experimental results and the CFD simulations demonstrate a good agreement, demonstrating that through adoption of a flash-boiling breakup model, it is possible to reproduce non-evaporating and superheated sprays while changing few simulation parameters. Finally, the results also show the significance of injection pressure in preventing spray collapse.