Despite the marginal growth recorded in the tourism sector in Kenya, the domestic visits and estimates fall far below the expectations. The study was guided by the following specific objective; to assess the moderating effect of contextual factors on the relationship between travel motivation and destination loyalty among domestic tourists in the Coast Region of Kenya. The study area comprised frequented attractions in the Coast region of Kenya. The study adopted an embedded mixed approach comprising descriptive survey and explanatory research designs. Simple random sampling and purposive techniques were adopted for domestic tourists, destination managers and experts respectively. Data was collected using questionnaires and interview schedules. Four hundred (400) questionnaires were distributed while 10 destination managers and 5 experts were interviewed. Data analysis was done using multiple regression models, hierarchical multiple regression and descriptive analysis. The multiple regression model results without interaction terms indicated that R-square = 0.442, implying that destination attributes and socio-psychological factors explain 44.2% of destination loyalty. The hierarchical multiple regression demonstrated that contextual factors have a moderating effect on interaction between travel motivation and destination loyalty since the model was significant {R2 = 0.255, F (7, 371) = 12.12, p =0.0001}. The model accounted for 25.5% of variation on destination loyalty. This means that the composite elements of contextual factors namely; political, economic, technological and socio-cultural factors significantly moderates the interaction between travel motivation and loyalty behaviour of domestic tourists. The null hypotheses were tested and rejected. The study recommends need for destinations and service providers to engage more on digital marketing and deploy technology during marketing initiatives and product development to capture niche segments since majority of the respondents were youth travelers