I'm going to Disney World! Should I stay on or off property?

Here’s a common Disney Debate: is it better to stay on or off property for your Disney World Vacation? This is actually a disputed topic within my own family - half of us stay on property, the other half stay off. Today, I’ll cover some of the biggest things travelers consider when booking their trip and compare Disney Resorts to non-Disney options. Here we go!
Cost
This is usually the #1 item to consider for any individual or family traveling to the Disney Parks. How do you get the most bang for your buck? Many believe that Disney Resort prices are high compared to surrounding hotels, but I just don’t find that this is the case. While it can certainly be cheaper to stay off property in some situations (splitting an off-property condo or rental house with a large group is one example) you have to keep in mind all the amenities you get at a Disney resort and decide if staying off property really does save you money. I’ve done extensive comparisons myself to see if I can get a better deal by staying off property, but I always end up staying at a Disney Resort.
As an example, I could stay at Disney’s Grand Floridian for one night for $617, or the nearby Four Seasons for $631 a night. Or, you could stay at Disney’s Pop Century for $115 a night, or the nearby Holiday Inn for $105. There isn’t actually that big a cost difference between Disney Resorts and the comparable off-property hotels. I’ll also mention that the off-property hotels often charge “resort fees” that aren’t included in the price of the room, which Disney does not do. In the long run you could end up spending a lot more to stay off property because of these hidden fees.
Transportation
Staying on-property at a Disney resort means you get as convenient and stress-free a vacation as you could possibly hope for. With your Disney Resort stay, you get free transportation to and from the airport with Disney’s Magical Express. You don't even have to get your bag off the airplane if you don’t want to - Disney will do that for you, and bring it right to your room!
You’ll also get super convenient transportation from your Disney hotel to all the surrounding Disney parks - either by bus, boat, or monorail. This is great if you are with a large group - you don't have to wait around for your fellow travelers to head to the park because you aren’t sharing a car. You can hop on the bus whenever you are ready to go, and the rest of your party can join you later!
Many off-property hotels in the Disney World area do provide some sort of free or cheap transportation to the parks. Some will also bring you to both Disney and Universal, which is great if you plan to visit both parks! You’ll just want to confirm with the hotel that they provide this service before booking if it’s important to you. In many cases, you’ll likely end up needing a rental car to get to/from the airport and parks. If you plan to travel to Universal Studios, or any other non-Disney locations in the area, then this might make the most sense for you.
Proximity
Many of the Disney Resort Hotels - especially the Deluxe Resorts - are extremely close to the Disney Parks. You can walk right into Epcot from the Boardwalk, or the Yacht & Beach Club. If you stay at the Contemporary, Grand Floridian or Polynesian, you could hop on the monorail and be at Epcot or the Magic Kingdom in no time at all.
This close proximity to the parks is extremely helpful if you have young kids and plan to head back to the hotel for a nap part way through the day. You save so much time by staying at one of the on-property hotels, and it will be easy to return to the parks in the evening for the fireworks!
There are a few non-Disney-owned hotels that are within walking distance of Disney property, such as the Swan & Dolphin, or any of the hotels in the Disney Springs area. If staying off property near Disney Springs, you can walk right over to the Disney Springs bus area and hop on a Disney bus to any of the parks! The walk might be a bit further than that at the Disney Resort Hotels, but this is a great option if you really want to stay off-property.
Dining
It’s true that eating in the Disney Parks and the surrounding resorts can be very pricey. In some cases, the Disney Dining Plan can be a great value and save you lots of money, but that’s a topic for another day. If you’d like the Disney Dining Plan, then you’d have to stay on property. A few times a year, Disney offers the free dining plan with your stay which is truly an awesome deal. You could save as much as $70 per person per day, or more!
If you stay off property and rent a car, then you will have endless food options in the Orlando area and can probably save quite a bit of money as well. If you have a kitchen included with your accommodations, then it’d be worth making a trip to a local grocery store to prepare your own food for the week. You could also stay at a hotel offering free continental breakfast, and added perk that no Disney Resorts offer.
Extra Magic Hours
For me, this is a HUGE reason to stay on property. Each day, one Disney World Park will open early or stay open a few hours later, but only for guests staying on-property. This means you have access to all the rides and attractions with significantly shorter wait times. My brother and I were once able to run back and forth from Rock’n’Roller Coaster to Tower of Terror at least 6 times, and NEVER wait in line. Best. Night. Ever.
If you stay off property, you obviously miss out on this huge perk. So there’s that.
Theme
This one totally comes down to your preference. Do you want to have a completely immersive Disney experience and cut yourself off from the real world? Then you need to stay on property. The Disney Resort Hotels keep that Disney magic alive for you throughout your stay - you never have to interact with anyone but fellow Disney Vacationers, and Disney Cast Members. The theming ranges from tasteful, to over-the-top crazy depending on what resort and room type you choose. If you are traveling with kids, go for the crazy rooms at the Art of Animation or Pop Century resorts! If you want something more subtle, check out the Contemporary, or Port Orleans Riverside & French Quarter (just as a few examples.)
If you think you are going to want a break from Disney, then definitely choose a resort off property. Not everyone is as Disney-obsessed as me, so you might prefer a quiet, normal hotel with no Disney Magic to be seen.
Hotel Quality
The quality of the on-property hotel rooms varies depending on the resort. If you are willing to dish out the big bucks and stay at a deluxe resort, you are bound to get a really great and spacious room. On-property value and moderate resort rooms can be a bit run down at times, so I’d recommend looking for a hotel that has recently been renovated.
The comparable off-property hotels can definitely be a bit nicer.
Conclusion
To me, the bottom line is convenience. This is a vacation after all! There should be no effort involved. Staying at a Disney property means no rental car, no paying for parking, no sitting in traffic, and extra time in the parks each day. It also means I’m totally immersed in the Disney Magic from the second I step off my plane. Often times a Disney Resort means a lower cost as well, despite what you may have heard.
That being said, if you are someone who doesn’t care about any of the extra perks like transportation or extra magic hours, if you have rewards points to use at an area hotel chain, if you plan to spend a decent amount of time outside of the Disney Parks, or if you are traveling with a large group and find an awesome condo or home to rent, then it may make sense for you to stay off property. It all depends on what your situation is.
90% of the time, staying on property is your best bet, though there are definitely circumstances where you should consider an alternative. I hope this post has given you some idea as to what direction you should go!