The past few decades have seen a transformation in Sri Lanka from a traditional agricultural based rural economy to a more diversified economy leading to more pluriactive farmers. Pluriactivity has been identified as a survival and/or capital accumulation strategy. However, available literature reveals that all the pluriactive households are not socio-economically better-off. The objective of the research is to compare and contrast better-off and worse-off pluriactive households in a given locality. This is in terms of the nature of income generation activities carried out by them and will be discussed in line with theories of entrepreneurship. Multiple embedded case study strategy was adopted. This was in order to explore meanings attached to socio-economic behaviours as perceived by the rural households. The research was carried out in a selected village in Kurunegala district, Sri Lanka. Initially, households were divided into soio-economically better off and worse off groups based on information gathered from key informants and subsequently, two samples were drawn from each group. Multiple data collection methods such as in-depth interviews, group discussions and direct observations were used. The data were analysed qualitatively and the findings were supplemented with quantifiable evidences whenever necessary in order to increase the validity of conclusions. The study site was a typical example of a resource constrained environment and pluriactivty has been adapted by both groups in order to increase their household income. However, the better off households have diversified into more off farm income generation activities and hence their dependency on agriculture was lower than that of worse off households who were mainly dependant on agricultural activities. In addition, the better off households exhibited more entrepreneurial qualities as they extract values from the environment without regard to the resource owned by them.