Last Summer we drove from NJ and brought Winston (shown in my avatar) with us. We stayed at pet friendly hotels on I-95 (plenty of nice ones to choose from, btw), and rented a house about 10 mins. from Disney, and stayed 2 weeks.
We had Winston booked at the Disney Kennel for many of the days we spent at the parks. The kennel, staff and accommodations were really nice. We got pretty much the best package they offered, such as personal time, walks, special snack, etc. Again, the place was top notch!
Around very early evening, right before dinner at Ohana, we called to see how he was making out, and the staff said he was very nervous and wouldn't relax/nap, eat or even do his business outside. Winston's spoiled silly, so we cancelled all the rest of the days, and he chilled at the rental house and made out just fine.
Heck, he's a Bulldog after all, they pretty much sleep all day
Now, the tough part for us is that we're leaving in just under a month for Disney, and he's staying home with our 3 cats for 6 days.
We already have 3 neighbors scheduled to take care of him and the cats. His treats will be plentiful (like they're never not,lol...), and we purchased new play toys for every day we're away.
We just don't wish to board him, and we've got super friends/family that he's very comfortable around, and we know he'll be just fine. The instructions I have printed out for each of his caretakers are very specific, and of course we're always a phone call/text away.