I took my dog to a kennel for the first time last year when we went to Las Vegas. I won't take him to a regular kennel again, I felt horrible leaving him there for 8 nights, and from now on I am either letting my parents watch him or I am going to pay more and take him to a place near my house that is more like a pet hotel than a kennel. I worried about my dog the whole time I was on vacation. If you must do a kennel, check it out in advance, some kennels have small cages and the dogs hardley get out, some have big, nice areas that are like 6' x 8' and have an outdoor run attached so that when the kennel is open during the day your dog can go outside when he wants to. My experience was awful. I took my dog to his "stay" right on our way to the airport, fully expecting to be able to bring him all the way into his "room" and putting his bed and toys in there with him and telling him I would be back soon. Instead, the kennel owners refused to let me even SEE what the kennels looked like, in fact, they just took him from me in the lobby, and they could see how distraught and everything I was and still refused my request, they told me I would disturb the other dogs and upset them. So, unfortunately, I had to leave him and that was it. I left in tears and feeling totally horrible. I will never use them again.
We don't go to WDW until late August, but I am already having anxiety about leaving him, and I think I am just going to have to burden my parents with caring for him. At least then I know he will be treated well and will be in good hands.
My other suggestion is that you search all over, and try and find a place that is not kennel like. (search using internet) I live in Indiana, we have a place about 40 min. from here called "Auntie Barbara's". It looks wonderful, the dogs get their own rooms, like real bedrooms with a tv and everything (don't laugh, my dog watches tv!) and the kennel is actually a home! It is great, $25.00 per day, but well worth it if I have no other means. I would suggest internet searching and I would book as soon as you can because good places fill up fast, don't get stuck like I did and have to take anything that is left. It will ruin your vacation. Good luck and I hope you find a place that will give you peace of mind.