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The first consideration is whether you will stay inside Walt Disney World or outside of it. If you plan to spend your entire vacation at Disney, then you will generally want a hotel on Disney property. Additionally, if you are flying into Orlando, then you will generally want to stay at a Disney-owned hotel on Disney property.

Staying at a Disney-owned hotel allows you to take advantage of the Disney transportation system, which provides comfortable and efficient access to all Disney attractions via bus, boat, and monorail. Additionally, Disney hotels provide free transportation to and from Orlando International Airport via the "Magical Express" buses. Therefore, it should neither be necessary to rent a car for an all-Disney vacation nor to worry about driving and parking your own vehicle. Additionally, if you have reasonably well-behaved teenagers, you can turn them loose in the park without having to worry about transporting them or reconciling all of the conflicts between your desired itinerary and theirs.

On the other hand, if you also plan to visit other Orlando-area attractions such as Universal Studios or the Holy Land Experience, you will need a car and will be better served by staying in an off-site hotel. Few Disney resorts offer car parking that is convenient to the guest rooms. Additionally, Disney World is a long way from other Orlando-area attractions, and Disney property itself is so vast that many of the hotels located there are long drives from the entrances and exits.

Likewise, if you want to rent a condo or kitchenette, then you may want to stay off-world even if you are taking an all-Disney vacation. The Disney-owned Fort Wilderness Resort and Campground offers cabins for rent, but otherwise the only condominiums available on Disney property are those affiliated with the Disney Vacation Club time-share program. The time-share "villas" are available for rent to the general public when the club members are not using them. However, you can probably get more for your money by staying off site.

Not all of the hotels located on Disney property are owned by Disney. Several are owned by third-party operators such as Hilton and Starwood. These third-party properties generally offer better value for your money than the Disney-owned resorts, but only one of them, the Starwood Swan and Dolphin, connects to the main Disney transportation system. The other resorts provide more limited shuttle services that are not really a desirable substitute

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