This paper presents a six-month exploratory case study on the evaluation of three Haptic Music Players (HMPs) with four pre-verbal children with Profound and Multiple Learning Disabilities (PMLD). The evaluated HMPs were 1) a commercially available haptic pillow, 2) a haptic device embedded in a modified plush-toy backpack, and 3) a custom-built plush toy with a built-in speaker and tactile shaker. We evaluated the HMPs through qualitative interviews with a teacher who served as a proxy for the preverbal children participating in the study; the teacher augmented the students’ communication by reporting observations from each test session. The interviews explored functionality, accessibility, versus user experience aspects of respective HMP and revealed significant differences between devices. Our findings highlighted the influence of physical affordances provided by the HMP designs and the importance of a playful design in this context. Results suggested that sufficient time should be allocated to HMP familiarization prior to any evaluation procedure, since experiencing musical haptics through objects is a novel experience that might require some time to get used to. We discuss design considerations for Haptic Music Players and provide suggestions for future developments of multimodal systems dedicated to enhancing music listening in special education settings.