Are you planning a family trip? Surely you have been dreaming of just the right vacation—sitting beside a crackling fireplace, curling up at a sunlit beach, or an ambling journey through a quaint mountain town. But before you get too excited, there is one thing you have to do: Where to stay?

The right rental can be the highlight of your vacation, while a poor choice can quickly turn it into a disappointing experience. After all, no one wants to book a place promising an “ocean view” only to find out it is just a little puddle in the parking lot.