While island resorts in the South Pacific are primarily marketed as sun, sea and sand destinations, cultural dimensions value-add to and diversify the product for mixed audiences. Resort developments require, at minimum, the compliance with legally mandated environmental standards and adherence to national employment legislation. Socio-culturally and environmentally sustainable tourism concepts should exceed mandated environmental standards and be characterised by a close involvement with and respect for the expectations of local host communities who may hold land and/or traditional usufruct rights. But do resort developments comply? Using an example of a resort established on free-hold land during the pioneering days of resort development in Fiji, the aim of this paper is to provide a deliberation of the tension between organic resort development and sustainable tourism on private land. It will show that, where cultural and environmental planning controls were absent, development not only could progress unfettered but also that changes to tourism philosophies are not necessarily reflected in changes to a resort. The island of Malolo Lailai (Viti Levu, Fiji) has a rich and multi-layered history and heritage (Fijian, European and Chinese plantations, resort development) that provides an opportunity to value-add to the tourist experience. In reality, however, the ongoing resort development extinguishes past histories in favour of a post-occupation, twentieth-century colonial settler narrative, where heritage sites are merely allowed to co-exist provided they do not impact on resort development objectives. It demonstrates that, in the absence of external regulatory controls, the resort owner’s philosophy dominates and shapes the tourist experience.