I've lurked on here for a while and wanted to weigh in as someone else with some experience with a dog on Disney World property. Since the dog policy was announced last year we've made three trips to Yacht Club, two trips to Fort Wilderness Cabins and one trip to Port Orleans Riverside. Prior to Disney designating dog friendly hotels we had rented an RV from one of the providers who offer delivery to Fort Wilderness for three previous trips with our dog as it was the only way we could have our dog with us.
Outside of Disney we travel frequently with our small dog--we both travel frequently for work so whenever we travel personally we prefer dog friendly destinations so it is not additional time apart from him.
We have found Disney's dog policies similar to what we see at non-Disney resorts and destinations, dogs aren't allowed in food and beverage locations, pools and fitness centers but anywhere else is typically okay. When the dog friendly hotels were first announced there was so much bad information out about what you could and couldn't do we almost cancelled that first trip after the new policy was instituted because we thought the dog was only allowed in the hotel room and in the designated relief area and nowhere else. Disney has now posted each property's rules on the individual hotel's web pages which has made making an informed decision much easier.
Our dog is crated during the day while we are at work so being in a crate for part of the day while we enjoy the parks isn't an issue and the resorts all have so much outdoor space to explore and people watch it really feels like he loves the time with us at Disney World.
Fort Wilderness has miles of sidewalks to explore on foot or on a golf cart, we were here right after Christmas last year and checking out all of the campsite decorations was especially fun. Many RV-ers have RVs specifically so they can easily travel with their dogs so it is always fun meeting people at the dog park.
Port Orleans Riverside we really liked--walking along the Sassagoula River and the rest of the property at night or just people watching outside of the Steamboat Company as the horse and carriage comes and goes while enjoying an ice cream.
Yacht Club is probably our favorite Disney resort and we've enjoyed our time there with our dog walking along the board walk and watching the boats on Crescent Lake. According to the Yacht and Beach Club Recreation Team's Instagram (
ybresortactivities) they are even offering a dog play time, treats, and paw-art projects on Sunday afternoons at the tennis courts. We haven't stayed here since they started offering this but plan to take advantage of it on a trip in the coming months.
In general my advice would be if your dog is comfortable in a crate during the day and you already travel regularly with your dog and your dog travels well I wouldn't hesitate to also take them along on a trip to Disney World. If you've never taken your dog on an overnight trip I'd probably not recommend Disney World being your first dog friendly destination.