Habanero pepper production was assessed with drip irrigation and plastic mulch, based on two transplanting dates. The objectives of the study were: (i) to evaluate the effect of two transplanting dates and the use of plastic mulch on water productivity and habanero pepper fruit yield under drip irrigation conditions; and (ii) to determine the profitability and economic viability of the product in the regional market. The work was conducted in the municipality of Huimanguillo, state of Tabasco, Mexico, in loam soils classified as Eutric Fluvisol. The Jaguar variety of habanero pepper, developed by INIFAP and possessing better genetic and productive characteristics, was used. Two transplanting dates were studied, (i) 30 January 2013 and (ii) 15 February 2013, with and without plastic mulch. The conclusions were: (i) application of irrigation depths based on crop evapotranspiration (ETc) and plastic mulch transplanted on 30 January increased the fruit yield of the crop and improved the benefit–cost ratio of the production system; and (ii) water use efficiency based on the 30 January transplanting date was 8.68 kg m−3 of water applied with plastic mulch, 6.51 kg m−3 without plastic mulch, and 3.65 kg m−3 for the 15 February transplanting date with plastic mulch.