It is well recognised that there can be strong emotional bonds between people and the properties where earlier generations have farmed and lived. These relations outrun economic reason and affect how individuals act, plan and relate to these places today and in the future. But what about the bonds and acts regarding a second home, a leisure place that mainly is a consequence of our modern, urban society? Many second homes are being shared within families and several generations may jointly use second homes. This chapter examines second home usage within families and over generations. It analyses second home users’ enactment, including their thinking, feeling and acting, of their second home in relation to existing or future shared usage/ownership and generational change. Four different materials are used: a questionnaire survey of second home users, interviews of second home users, media discourse, and a survey. The results show that the bonds to the second home property are strong but vary between owners, the bonds being stronger among owners who inherited the property as compared to owners who had bought it. Conflicts between family members often start when the authority over the second home is being transferred between generations. It is not only those who live today that have to be taken into consideration when making decisions, but also those who had lived before and those who will come after are significant.