In this study, the surface roughness, dimensional accuracy, and circular and cylindrical deviations characterizing the hole quality were investigated experimentally. AISI 1050 steel in experiments was chosen as reference material due to its extensive applications in many areas. Uncoated and TiAlN coated by physical vapor deposition (PVD) method HSS twist drills with different diameters were used. Experiments were conducted on a CNC vertical machining center under dry condition with different cutting speeds and feed rates. The hole depth was 17 mm to ensure L < 3D condition. After each experiment, hole properties such as surface roughness, dimensional accuracy, circular deviation, and axial misalignment between inlet and outlet holes (cylindrical deviation), all of those that show the hole quality, were measured, and the results were evaluated. In addition to experimental analysis, a statistical analysis was carried out to indicate the effects of drilling parameters on test results. Process parameters such as tool type, drill diameter, feed rate, and cutting speed were optimized with consideration of multiple performance characteristics using desirability functional analysis. As a result, coated tools compared with uncoated tools gave positive results for each evaluation criterion. As the most important parameter on surface roughness (Ra) was drill diameter, the most effective parameter on dimensional accuracy, and circular and cylindrical deviations was cutting speed for both uncoated and coated tools except from cylindrical deviation occurring in uncoated drill.