The Magic of Staying at a Disney Resort
Many people who have been going to Walt Disney World since the 1980s will tell you about the days of waiting in the TTC parking lot waiting for your bus back to your resort on International Drive. It was a painful, unpleasant experience most of the time. Whether it was the sun beating down on you or the pouring rain, you missed a bus, and you paid for it.
Back then, Walt Disney World had 3 resorts (Contemporary, Polynesian, Fort Wilderness). They were expensive and for a family, often that meant staying off-property at International Drive. Once you got back to your hotel though, there was Wet and Wild, shopping, dining, and fun. It was the bus that made it so unpleasant.
Then something miraculous happened. Walt Disney World got Moderate, then Value resorts. That changed everything.
Once the different categories of resorts became available to guests, more began staying on property. Disney Transport buses eliminate the 60 minute wait for your next bus departure and you never left the resort, making your vacation all-Disney, all the time.
With 20+ resorts and tens of thousands of rooms, Walt Disney World Resort hotels are a great option for guests at literally all price levels.
Personally, I've stayed at 5 different resorts (Port Orleans French, Port Orleans Riverside, All Star Sports, All Star Movies, Art of Animation) and loved each of them, even the All Stars!
I've never paid rack rate (full price) for the rooms, but did overpay once due to an expected re-booking that happened.
The benefits of staying on-property include the transportation, theming of the resorts, staying in the magic bubble of the resort property and easy access to almost everything on-property. You never leave the magic, unless you go through the sometimes exhausting steps to do so.
That brings me to the only drawback. If you're planning to go to other theme parks, or places like the Kennedy Space Center, it isn't easy. It's not impossible, but you either need to plan ahead or rent a car.
In any case, I love staying on property and it breaks my heart to see those people sitting by the bus lane waiting for the transportation off-property.