Optically stimulated luminescence (OSL) dating is now commonly used to estimate the depositional age of Quaternary landforms along the southern Cape coast of South Africa. Due to the early onset of dose saturation in the quartz-rich sediments from this region, determining the age of deposits much older than the last three glacio-eustatic sea-level high stands has been a challenge. In this study, we explored the feasibility of using the thermally-transferred OSL (TT-OSL) dating method to obtain ages for aeolian and shallow marine deposits at three different localities that hold promise to further illuminate the long and complex Late Quaternary sea-level history of this region. The bleachability and behaviour of both the recuperated OSL (ReOSL) and the basic-transferred OSL (BT-OSL) signals were investigated, and used as independent chronometers to infer (a) the degree of bleaching of the sediments and (b) the stability of the ReOSL signal for dating of older samples. We examined the sensitivity of both signals to varying preheat temperatures and further developed the single-aliquot regenerative-dose procedure for TT-OSL dating of our samples. To verify our procedures, and to understand some of the underlying mechanisms responsible for the problems we observed, modern analogues and known-age Marine Isotope Sub-stage (MIS) 5e samples from the same localities were also measured. The Middle Pleistocene deposits investigated in this study produced statistically consistent ReOSL and BT-OSL ages compatible with sea-level high stands during Marine Isotope Stage 11. This result is of considerable significance, as it may yield new insights into maximum sea-level heights during this period, which is widely considered an appropriate analogue for future environmental conditions.