Virginia Woolf with her great talent as a writer and thinker has achieved canonical status in world literature. There is no doubt that she was one of the most distinguished modernist writers in the twentieth century and her works continue to have an impact in today’s world. When Virginia Woolf was first introduced to Taiwan’s readers in 1960, her works were indeed seen as a stimulus to contemporary literary production, but it wasn’t until the 1990s that Woolf’s works were translated into Chinese on a larger scale and became more widely acknowledged by Taiwan’s readership. However, only certain novels were translated and in some cases, a single text gave rise to three or four different translations. The film productions of Orlando (1993) and The Hours (2003) have played an important role in promoting Woolf’s popularity in Taiwan. This article will attempt to examine Orlando, one of her most popular works in Taiwan, and investigate how different translators render this witty and poetic text. Orlando was first translated into Chinese in 1993, the same year the film version was released in Taiwan, and since then, four more versions of the work have appeared on the market (the most recent one being released in 2008). Why did the publishers want to produce different versions? What images do these four translations represent? What translation strategies do the translators adopt in order to deal with Woolf’s innovative style? This study applies the theoretical frameworks of Gérard Genette and of André Lefevere in order to investigate the four recent translations of Virginia Woolf’s Orlando. In addition, Shan Te-hsing’s concept of “double contextualization” fittingly explains how a translated work should be placed in the target culture. It is hoped that this case study can shed new light on the historiography of literary translation in Taiwan in particular and of translation studies in general.