Lifestyle relocation is a highly privileged form of mobility. However, the extent of such privilege needs to be addressed theoretically and empirically in countries such as Spain where lifestyle migration is rising. This article dissects the extent of such privilege by analyzing the economic advantages and challenges that different social groups have when acquiring properties for lifestyle reasons. By lifestyle reasons we understand here a mix of economic, leisure and life change motivations underlying lifestyle migrants' property acquisition.To explore the unequal advantages and challenges faced by lifestyle migrants, we explore the variegated economic strategies conducted by Swedish lifestyle migrants in the property markets in the coastal areas of Majorca, Costa del Sol and Costa Blanca in Spain. Such trajectories that illustrate the extent of the privilege of lifestyle migrants are analyzed by (i) dissecting the privileged position of lifestyle migrants in what Wright labelled as the 'relations of production'; by (ii) exploring how the position in the relations of production intersect with other social structures and particularly age, gender and civil status; and by (iii) categorizing the trajectories of Swedish lifestyle migrants in the Spanish housing market according to three main positions of privilege: less advantaged, advantaged and super advantaged.