In the Netherlands, there will be an urgent need for additional housing by the year 2040, which mainly has to be realized within the existing built environment rather than in the spatial extension of cities. In this data-driven study, we investigated the effects of different urban planning strategies on heat stress for the current climate and future climate scenarios (year 2050) for the urban agglomeration of The Hague. Heat stress is here expressed as the number of days exceeding minimum temperatures of 20 °C in a year. Thereto, we applied a diagnostic equation to determine the daily maximum urban heat island based on routine meteorological observations and straightforward urban morphological properties including the sky-view factor and the vegetation fraction. Moreover, we utilized the Royal Netherlands Meteorological Institute’s (KNMI) climate scenarios to transform present-day meteorological hourly time series into the future time series. The urban planning strategies differ in replacing low- and mid-rise buildings with high-rise buildings (which reduces the sky-view factor), and constructing buildings on green areas (which reduces the vegetation fraction). We found that, in most cases, the vegetation fraction is a more critical parameter than the sky-view factor to minimize the extra heat stress incurred when densifying the neighbourhood. This means that an urban planning strategy consisting of high-rise buildings and preserved green areas is often the best solution. Still, climate change will have a larger impact on heat stress for the year 2050 than the imposed urban densification.