This study aimed to assess the feasibility of the Apple AirPods Pro with the headphone accommodation feature as a hearing assistive device for patients with mild to moderate hearing loss (HL). The study included a total of 35 participants with mild to moderate HL. To determine the degree of HL in the participants, a screening test using pure-tone audiometry was conducted prior to the main tests of functional gain, word recognition score (WRS), and sentence recognition in noisy environments. The study employed two hearing devices: the Bean (a personal sound amplification product, PSAP) and the AirPods Pro. Regarding functional gain, there were no significant differences between the Bean and the AirPods Pro at all frequencies, except 8 kHz. In terms of WRS, both the Bean and the AirPods Pro had higher scores than the unaided condition. In sentence recognition, both the Bean and the AirPods Pro had higher scores than the unaided condition. During real-ear measurement, the Bean demonstrated consistent frequency responses, while the AirPods had a deviation exceeding 10 dB SPL at 6 kHz in the left ear. This deviation was absent for all other frequencies. This study shows that the Apple AirPods Pro, with its headphone accommodation feature, performed similarly to a validated PSAP and improved hearing compared to unaided conditions.