My introduction to vacation rentals came shortly after my first child was born, when my wife and I somehow got it in our heads that it would be a good idea to take a vacation not only with my wife's parents but also with her brother and his wife and my wife's grandparents. I pictured the nine of us crowded together in a small cabin in New Hampshire with no room to move around and nothing to entertain us but the misadventures of my in-laws' corgi, cat, and cockatoo. (Yes, they all joined us, too.)
It turns out my fears were misplaced. We had plenty of space, plenty to do—the rental was on a lake with its own private dock—and plenty of money left over after booking to spend on food and activities. As introductions go, my first brush with the art of renting a vacation property couldn't have gone much better. But the truth is I got lucky that first time. I didn't know what I didn't know about vacation rentals.
We've rented a new place every summer since then, sometimes here in the U.S. and sometimes overseas, and each year I've added a few new rules to my list of what to look for, what to ask, when to book, and when to walk away from a rental agreement. So whether you're new to vacation rentals or need a refresher course on how to go about picking the right one for your next trip, follow these eight steps and you'll be relaxing in the perfect property in no time.