(1) Background: This study aimed to evaluate and compare the clinical optical image quality following implantation with different premium IOLs by the analysis of the point spread function (PSF) Strehl ratio using a Pyramidal WaveFront-based sensor (PWS) aberrometer at two different pupil sizes. (2) Methods: This study included 96 eyes of 70 patients implanted with: (1) 19 AcrySof SA60AT (control group); (2) 24 LENTIS Mplus LS-313 MF30; (3) 33 LENTIS Mplus LS-313 MF15; and (4) 20 Precizon Presbyopic. Main outcome measures were PSF Strehl ratio, PSF Strehl ratio excluding second-order aberrations (PSFw2), total root-mean-square (RMS), and low- and high-order aberrations’ RMS measured by PWS aberrometer. Results: SA60AT had the highest significant PSFw2 Strehl ratio at both 3- and 4-mm pupil size (0.41 ± 0.11 and 0.28 ± 0.07) followed by LENTIS Mplus 15 (group C, 0.35 ± 0.1 and 0.21 ± 0.06) and a near tie between LENTIS MPLUS 30 (group B, 0.27 ± 0.08 and 0.18 ± 0.06) and Precizon Presbyopic (group D, 0.27 ± 0.07 and 0.17 ± 0.04). MPlus MF15 was found to be significantly better than MPlus MF30 at both 3.00 mm (p < 0.0001) and 4.00 mm (p = 0.002). (4) Conclusions: The PSFw2 represents a new tool to objectively evaluate the far distance retinal image quality of multifocal IOLs, and the far distance clinical image quality parameters measured by PWS aberrometer differed significantly according to the technology of the implanted lens.