This chapter focuses on home-based economic activities (HBEAs) in two Caribbean cities. These income-generating activities are financially, socially and spatially strongly integrated within the household. In the Global South they are, after paid work, the most often performed type of livelihood activity. HBEAs vary in terms of type of activity, the role they play in livelihoods, and how space, skills, labour and funds are used in their operation. The chapter addresses the relationship between HBEAs and the institutions and social relations functioning at the neighbourhood level. It asks how these neighbourhood relations are shaped by the role HBEAs play in household livelihoods and by their patterns of operation. Empirical findings show that for HBEAs neighbourhood relationships are extremely complex and provide HBEAs with huge benefits but also pose core constraints. Most HBEAs rely on the community for their market. Positive aspects for the operators are general support by community members and the familiarity with and short distance to the market. On the negative side, the neighbourhood as market is small and has limited purchasing power. Operators are forced to sell goods very cheaply, have to deal with huge competition and need to provide unreliable credit. They are limited in their ambition to grow because this will trigger negative reactions from neighbours. HBEAs that are informal and provide modest and supplementary incomes and have the community as a market are much more affected by neighbourhood relations than HBEAs that operate in a more formal manner.