Background: To identify factors necessary for the proper inclusion of foreigners in Japanese healthcare, we conducted a survey to determine whether foreign residents, even those with high socioeconomic status, referred to as “Highly Skilled Foreign Professionals”, experience difficulties when visiting medical institutions in Japan, using satisfaction level as an indicator. Method: A five-point Likert-scale, anonymous, online questionnaire was administered to faculty and doctoral students enrolled at the Okinawa Institute of Science and Technology Graduate University (OIST). The respondents’ demographics and their opinions on what they found difficult or important during medical examinations, their impression of Japanese medical personnel, their requirements for language support and interpretation, and their opinions about local healthcare delivery systems were collected. The questionnaires were distributed and collected using Microsoft Forms. Results: Responses were obtained from 90 respondents (response rate: 20.7%). The percentage of respondents who were dissatisfied (bottom two of five Likert scales) with medical care in Japan was 23.4%. In univariate logistic regression analysis, 11 of 35 questions were significantly correlated with dissatisfaction with medical care (p < 0.1). Duration of stay, presence of family members living with the patient, satisfaction with life, and perceived usefulness of language support were negatively correlated with dissatisfaction with medical care, while communication problems with medical personnel, need for medical personnel to respect patients’ culture, religion, and privacy, and difficulty in getting to medical facilities were positively correlated with dissatisfaction with medical care. No significant correlations were found with age, gender, or Japanese language level. Multiple logistic regression analysis showed that the presence of family members living with the subject (AOR = 0.092, p = 0.010), the desire for multilingual documentation (AOR = 0.177, p = 0.046), the physician’s concern for the patient’s culture and religion (AOR = 8.347, p = 0.029), and difficulty in communication with healthcare providers (AOR = 6.54, p = 0.036) were significantly correlated with overall dissatisfaction with medical care. Discussion: On average, the targeted Highly Skilled Foreign Professionals did not have strong levels of dissatisfaction with Japanese healthcare, but when they did have dissatisfaction, it was related to language barriers, lack of cultural and religious considerations, and difficulty in communication with healthcare providers. We believe that the results indicate the focus points of support necessary for the inclusion of foreigners. We also believe that the finding that family cohabitation is associated with satisfaction with medical care is a useful insight into effective reciprocal support on the part of patients.