Rock slopes involved in extensive landslide processes are often characterized by complex morphodynamics acting at different scales of space and time, responsible for different evolutionary scenarios. Mass Rock Creep (MRC) is a critical process for long-term geomorphological evolution of slopes and can likewise characterize actively retreating coastal cliffs where, in addition, landslides of different typologies and size superimpose in space and time to marine processes. The rocky coast at the Conero promontory (central Adriatic Sea, Italy) offers a rare opportunity for better understanding the predisposing role of the morphostructural setting on coastal slope instability on a long-time scale. In fact, the area presents several landslides of different typologies and size and state of activity, together with a wide set of landforms and structural features effective for better comprehending the evolution mechanisms of slope instability processes. Different investigation methods were implemented; in particular, traditional geomorphological and structural field surveys were combined with land surface quantitative analysis based on a Digital Elevation Model (DEM) with ground-resolution of 2 m. The results obtained demonstrate that MRC involves the entire coastal slope, which can be zoned in two distinct sectors as a function of a different morphostructural setting responsible for highly differentiated landslide processes. Therefore, at the long-time scale, two different morphodynamic styles can be depicted along the coastal slopes that correspond to specific evolutionary scenarios. The first scenario is characterized by MRC-driven, time-dependent slope processes involving the entire slope, whereas the second one includes force-driven slope processes acting at smaller space–time scales. The Conero promontory case study highlights that the relationships between slope shape and structural setting of the deforming areas are crucial for reaching critical volumes to induce generalized slope collapse as the final stage of the MRC process. The results from this study stress the importance of understanding the role of morphostructures as predisposing conditions for generalized slope failures along rocky coasts involved in MRC. The findings discussed here suggest the importance of the assessment of the slope instability at the long time scale for a better comprehension of the present-day slope dynamics and its major implications for landslide monitoring strategies and the hazard mitigation strategies.