After having to recently put down our 15-year-old beagle (sniff!) we now have just two dogs. We used to travel with them frequently to my parents' vacation home; however, we find that it's just too stressful on all of us to even think of taking them to WDW or any similar vacation. They aren't great at the kennel, so we now leave them at home and have them looked after by a combination of a very helpful neighbor, another neighbor's teenage sons (who know our dogs and work pretty cheap), and a professional dogsitter (who is not so cheap but very professional and great with the pups).
The dogs miss us, but they are more comfortable in their home environment than they would be on the road with us, and we know they are well taken care of.
BTW, there is a website somewhere (sorry I don't have the URL) which lists pet-friendly accomodations all over the country.