Usually it's hotels for my wife and I traveling. In fact we're headed out of town next week-going to spend 3 days going and 3 days coming on the road(a 1 year old makes travel a lot slower and makes us a lot less eager to put in full long days like the two of us alone might do). We'll stay with my parents in Kentucky for one of the nights each direction, and then hotels on the road and at our destination.
Usually we do a big summer vacation with my wife's family, and Destin, FL is a favorite spot. They like Sandestin, and there are hotel options but on the whole renting a home is hard to beat. My FIL likes booking through VRBO, or the last few times has bypassed them and booked directly through owners of ones we've liked(some have ways to do that). Split 3 ways, it's usually quite a bit less expensive than 3 separate hotel rooms. Plus, we always look for rentals with a golf cart, which is a big deal there too. The kitchen is nice, and since I actually genuinely enjoy being around all of them, having shared spaces is nice too(but still our own rooms at the end of the day). Since our son and our nephew spend enough time together to be practically brothers anyway, it's a ton of fun to have the space together for them.
The only time we really had an issue was at the most recent one last summer, where a bunch of community-specific rules weren't communicated to us and we received citation for them. We were told to place garage at the curb for pick-up before 6:00AM daily, but weren't informed that it couldn't be set out earlier than 8PM the night before. When we checked in, the golf cart was only half on the parking pad-not only did we find it that way but weren't told that this was against community rules and were cited within an hour or two of check-in before we'd even touched the thing. There were bunches of other little issues with the unit we were staying in(some outlets not working, towel rods in the bathroom falling apart, door keypad randomly changing combinations twice during our stay, parking pad being small enough that getting two vehicles+golf cart on it and not hanging off was a coordinated multi-step operation, a few others I'm forgetting), none of which would have been a big deal by themselves but which added up to make a less than great stay. We would stay in that particular community again, now knowing their specific rules(and double/triple checking to make sure there weren't new ones) but not the unit we stayed in.