Introducing openings or holes into wooden structures is a common practice for providing utility services. However, this practice leads to stress concentration, resulting in a reduction in stiffness and load-carrying capacity. Therefore, understanding the effects of holes on beam properties is important for design considerations. This study investigates the mechanical behavior of a wooden beam made from juvenile Pinus elliottii containing open cylindrical holes with three different diameters: 4, 8, and 12 mm. The mechanical properties were evaluated for compression parallel to the fibers, quasi-static bending, and tension perpendicular to the fibers. Numerical simulations were conducted using a finite element (FE) model, considering the orthotropic elastic properties determined from experimental tests and elastic ratios reported in the literature. The experimental results indicated that the influence of hole diameter was not significant on the compressive properties; however, longitudinal crack failures began to form for holes with diameters of 8–12 mm. Regardless of hole size, the compressive and bending characteristics revealed that hole location did not affect the stiffness, strength, or damage mechanisms.