I never really understood this. Unsure of the US, but holiday lets are notorious for being poor investments in Europe (just look at the markets in Greece and Spain). $100k buys you quite a lot of long-term lets (rentals) over the next 20 years. Why not just rent a place without the hassle of maintenance, taxes, stress, and hand back the property after a few weeks? Also your priorities and interests might change, so some flexibility on renting different places at different points (with children that grow up and also have different interests) might be appealing.