The Kenyan government, in collaboration with other education stakeholders, has done a lot to improve retention and access in the Kenyan schools. However, the situation has not improved much in the schools within Lake Victoria islands of Suba district. The present study investigated the strategies head teachers employ to improve retention in primary schools in Lake Victoria islands of Suba district, Kenya. The study adopted descriptive survey research design with an ex-post-facto approach. Kiwa and Kibuogi primary schools were purposively sampled to be studied, being the only island schools in the district. Data was gathered using both interview schedules and questionnaires administered to two (2) head teachers, six (6) teachers, 86 school pupils and 16 primary school dropouts. The sixteen school dropouts were reached through snowball sampling technique. The collected data was presented and analyzed using both descriptive and inferential statistics with the aid of Statistical Package for Social Sciences (SPSS Version 16.0 program). It was observed that the main factors that lead to pupil drop out of school were unemployed educated family members, death of both or one parent and migration of parents. Other factors included early pregnancies, early marriages, uncaring polygamous fathers and poverty. The study findings revealed that the most effective strategies head teachers employ to improve retention were games and clubs, peer counseling, academic counseling, gender appropriate facilities and normal class size. These were obtained through rating of the responses from pupils, teachers and head teachers. Others were gender balanced staff and feeding programs.