I've heard lots of people say, "Shoot, I'm not staying at a Disney hotel. All that money when all I'll be doing is sleeping there? I don't think so."
The truth is, you're paying for a lot more than lodging. What folks don't often consider is that if you decide to stay off-property, you still have to drive to the parks - and pay around $14. You think traffic in the big city is bad? Try driving back to your hotel after the Magic Kingdom closes.
One of the great things about the Walt Disney World Resort is that it's its own working city, in a sort of bubble, complete with its own forms of transportation. Certain resorts offer transportation to the MK or Epcot via monorail, and all resorts offer bus transportation to guests. Buses, or motorcoaches as Disney calls them, arrive at the resorts and theme parks approximately every 20 minutes. True, the motorcoaches don't always allow for the most pleasant experience - like when you're standing for the 17-minute ride back to your resort - but trust me, it beats driving your own car.
See, if you did drive to the Magic Kingdom, you'd park in a lot by what's called the Transportation & Ticket Center, which is actually across the Seven Seas Lagoon from the MK itself. You'd have to take a CM-driven tram to the actual park entrance. Not so bad, but after a long day at the park, you'd have to wait in a massive line for the tram, walk to your car, and then wait in line to get out of the parking lot onto the main road, where traffic jams await. Doesn't sound fun to me.
Another great benefit of staying on-property is the extra time you're allowed in the parks. Every day, one park has Extra Magic Hours - which are extra hours either before that park officially opens, or after it officially closes. This is only open to resort guests. You're paying lots of money for your vacation, so why not maximize the time you can spend doing fun stuff? Plus, Big Thunder Mountain Railroad looks really cool at night. ;]
If you're flying to WDW, staying on-property means that complementary transporation - Disney's Magical Express - will be provided to and from the airport. No taxis for you!
Remember that Dining Plan I talked about? That's only available to Disney resort guests, and it saves a lot of money.
The shops at the theme parks are awesome - but who wants to worry about holding packages when you're riding corkscrews on Rock'n'Roller Coaster? If you stay at a Disney resort, they'll ship your packages to your resort, no problem.
Mr. Skeptic would now say, "But I can't afford it!" Actually, if you budget correctly, you can. The original resorts at WDW are the Grand Floridian, Contemporary, and Polynesian. These bad boys are several hundreds of dollars per person per night, and Disney realized that this does not suit the average guest's budget, so they've added plenty of resorts since then. There are others along the same price range as those three, all grouped in the deluxe resort tier. There are also moderate and value resorts. Basically, the more expensive the resort, the closer it is the parks.
A complete list of the resorts:
Yacht Club & Beach Club
Animal Kindgom Lodge
Walt Disney World Swan and Dolphins Resorts (not technically owned by Disney)
Port Orleans French Quarter
Port Orleans Riverside (formerly Dixie Landings)
Fort Wilderness Cabins
The moderate resorts are, obviously, moderately priced, and the value resorts are the least-expensive option.
And if I haven't managed to convince you that you should stay on Disney property, here's one last thing: staying on-property is FUN. Checking in and receiving your Key to the World card is FUN. All the resorts have various themes, and you'll notice that theme in the decorations, pools, restaurants/food courts, Cast Member costumes, and even the bedspreads.
That's it for now, folks. Have a magical day!