Competition from large businesses threatens the existence of Small and Medium Enterprises (SMEs) in Kenya. However, with the acceptance and adoption of e-commerce SMEs can compete with the established businesses in both local and global markets, but recent studies indicate a worrying trend on adoption of e-commerce by health related SMEs in Kenya. This research tested the effect of three contextual variables that is individual, technological, and external environmental variables on the adoption of Information Communication Technologies (ICTs) by SMEs in the health sector in Kenya. A cross-sectional survey design was used, and 172 semi-structured questionnaires were administered to the end-users. A Logit regression was applied in analyzing the influence of the three contextual factors on acceptance and adoption of ICT by SMEs. Results indicated that age, CEO’s ICT knowledge, relative advantage, government policies on ICT applications, and pressure from suppliers and customers were the main determinants of ICT adoption. The study recommended that government should develop a differentiated ICT policy and incorporate compulsory training in computer applications in the national school curriculum. In addition, SMEs should set a mechanism for monitoring the changes in technological innovations as the electronic marketplace evolves.