<p>To investigate the mechanical properties and fracture mechanisms of rock-like specimens containing a hole under water–rock interaction, uniaxial compression tests were conducted on five groups of rock-like specimens with different water contents (0%, 0.41%, 0.81%, 1.22%, and 1.62%). A high-definition imaging system was used to record the failure process, and scanning electron microscopy (SEM) was employed to clarify the mechanisms of damage evolution. The results show that increasing water content markedly modifies the mechanical response. Both the uniaxial compressive strength and elastic modulus decrease nonlinearly, and the post-peak response becomes noticeably more ductile at a water content of 1.62%. Meanwhile, the recoverable elastic energy prior to peak loading and its proportion decrease, whereas the dissipated energy and its proportion increase. Failure around the hole wall consistently proceeds through five stages: loading, local bulging, sustained ejection, pervasive ejection, and termination of ejection. With increasing water content, ejection initiates earlier, the failure duration is prolonged, and the overall process becomes less violent. The dominant failure mode gradually shifts from tensile-dominated failure to a mixed shear–tensile regime. The debris fractal dimension decreases from 2.2 to 1.7, indicating coarser fragmentation and a reduced overall degree of comminution. At the microscale, higher water content intensifies the development of pores and microcracks, weakens cementation, and increases fine particles, reflecting progressive microstructural degradation. Overall, degradation under water–rock interaction is governed by the coupled effects of physical lubrication, chemical dissolution, and stress redistribution. These findings provide a theoretical basis for evaluating the stability of surrounding rock masses in water-bearing environments.</p>