Cultural differences and cultural diversity, in today’s globalized world, is a challenge faced by individuals and organizations. The shrinkage of cultural boundaries across the world, as an impact of globalization, has made it imperative for global managers to possess the appropriate kind of skills that enables them to function effectively in diverse cross cultural settings. It is important for hotels to realize that customer cultural orientation are not identical all around the world and thus understanding customer cultural orientation is important in enhancing service quality. The study sought to evaluate how customers’ cultural orientation affects service quality expectations among 3-5 star hotels in Nairobi City County. The target population was 12 managers, 72 supervisors and 1220 customers. Yamane formula was used to calculate sample size of 61 supervisors and 301 customers. Purposive sampling was used to choose 12 hotel managers. Pretest for the questionnaire was undertaken to ascertain the reliability of the tool before embarking for actual data collection. Data analysis involved both descriptive and inferential analyses. Descriptive analysis included frequency, percentages, means and standard deviation whereas inferential analysis involved correlation and regression analysis. Pearson correlation coefficients revealed that that there was a positive and statistically significant correlation between customer cultural orientation and service quality of three to five star hotels in Nairobi City County. The study also found out that there was a positively and significant correlation between management perception and service quality of three to five star hotels in Nairobi City County. Finally, it was established that communication strategies had a positive and significant association with service quality of three to five star hotels in Nairobi City County. The model summary revealed that customer cultural orientation, management perception and communication strategies explains 53.9% of changes in service quality of three to five star hotels in Nairobi City County. Regression results showed that customer cultural orientation had a positive and statistically significant relationship with service quality of three to five star hotels. It was also established that management perception had positive and statistically significant relationship with service quality of three to five star hotels in Nairobi City County. Communication strategies had a positive and significant relationship with service quality of three to five star hotels in Nairobi City County. The study concluded that customer cultural orientation, management perception and communication strategies have a significant influence on the service quality expectations among 3-5 star hotel clients in Nairobi City County, Kenya. It was recommended that for the star hotels to offer quality services, there is need for the staff need to be updated on diversity in cultural orientation among the customers, take time to understand the needs of their customers, help clients to make decisions and learn more to get to know the diverse culture, language, perception, psychology, economy, political and social backgrounds of the clients. The managers and supervisors need to lead from the front by knowing diverse languages, culture and psychology to enable handle clients who may proof hard to handle by the other staff. Keywords: Customers cultural orientation, management of hospitality, communication strategies, service quality expectations, 3-5 star hotels, challenges