Among the existing Cultural Heritage settings, Underground Built Heritage (UBH) represents a peculiar case. The scarce or lack of knowledge and documentation of these spaces frequently limits their proper management, exploitation, and valorization. When mapping these environments for documentation purposes, the primary need is to achieve a complete, reliable, and adequate representation of the built spaces and their geometry. Terrestrial laser scanners were widely employed for this task, although the procedure is generally time-consuming and often lacks color information. Mobile Mapping Systems (MMSs) are nowadays fascinating and promising technologies for mapping underground structures, speeding up acquisition times. In this paper, mapping experiences (with two commercial tools and an in-house prototype) in UBH settings are presented, testing the different handheld mobile solutions to guarantee an accurate and reliable 3D digitization. Tests were performed in the selected case study of Camerano Caves (Italy), characterized by volumetric complexity, poor lighting conditions, and difficult accessibility. The aim of this research activity is not only to show the differences in the technological instruments used for 3D surveying, but rather to argue over the pros and cons of the systems, providing the community with best practices and rules for 3D data collection with handheld mobile systems. The experiments deliver promising results when compared with TLS data.