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Hi! I've had experience doing both. While it is definitely more convenient (and magical) to stay on property, we always find it cheaper in the long run to stay at a timeshare (that we also can get for a minimal cost). We usually drive and would rather be able to dictate where we drive and when rather than have to rely on buses. Also, we tend to save money elsewhere with eating breakfast at the hotel and bringing a lunch into the parks and then having one big meal in the park (usually dinner)!
However, we have also flown and I will say, the Disney Magical Express is VERY convenient, no need to pay for a taxi and it's no extra cost.
I will warn you. It is PACKED during the free dining plan promotion. Everyone wants to take advantage, so beware.

I've done both several times and for us, they were different vacations. I enjoy both for different reasons:

Off site is amazing for the space and getting to explore more of Orlando. We hung around the pool a lot, went outlet shopping, and only did 2 days at Disney. If we go adults only we prefer this style of vacation.

On site is so convenient if you will spending a lot of time at Disney, especially with kids. It's very easy for people in your party to come and go with the transportation service . Sometimes my parents will take LO back to the hotel while Dh and I stay a bit longer. When we stay off site we are at the park for the whole day which can be tiring for everyone.

We are going in March and staying at Caribbean Beach with the dining plan. We book more $$ meals when using the dining plan (character dining, etc) to make sure we get our money's worth.

Our on-site trip this year will actually cost $500 less than our off-site trip last year. We don't have to rent a car and won't be doing any off site extras like golf or shopping.

@kpc324: I did both. Last year, we stayed off-site and this year we stayed primarily at 2 resorts. (Split-stay) Yes sounds crazy but we pack up and move very easily. And I really wanted to check out Art of Animation.
At Disney World everything is spread out (as compared to Disneyland) so driving from Resort to parks vs. Off-site to parks is about the same if you pick a good off-site place. You pay about $20 for parking vs. free parking from the resort so add that to the cost as well as the rental car. We drove in from the resort because I don't like being dependent on the bus system/times. The $ that would have gone to parking money (if I didn't stay at the resort) went to the car rental. We got a nice sized car for $20 a day (including taxes) for our stay. We also got to eat at some yummy off-property Mexican food for a little cheaper than Park price.
To add more complication but more fun, my mom, LO and I took the Disney Magical Express in as DH had to fly in a day later and picked up the car.

Also if you are planning to use shuttle/bus system from off-site property the times are super inconvenient in most cases. In case you are wondering, I only slightly prefer staying on site over off site for the transportation perks but the benefits of getting to book your fast passes 60 days out rather than 30 blows every other reason out of the water. I was able to book every ride I wanted at all the parks for the entire trip, not to mention the free parking, bus system, Disney hospitality, theming, and free magic bands.

We've done both and I prefer using our timeshare and staying off property. We rent a two bedroom suite which makes things much more comfortable. I also prefer having a car to having to wait around for the bus. However, being able to book fast passes and dining early is one big advantage to staying on property.

As for the Resort DINING perk, you get to book from the first day of your vacation for your entire vacation rather than 180 days from each day of your vacation. So if you are staying at the resort for 5 days, you get to book 185 days out for all days of your vacation. If you are off property, you would have to wait until 180 days and then login each day afterward if you wanted to book a different place everyday at the beginning of your window. We got into all the preferred, hard to get restaurants because we were at the resort. It was amazing to have one awesome dining experience a day! I was online at the exact moment the reservations opened up according to my vacation dates!

Monorail hotels are definitely the most convenient in terms of transportation but they are $$$$. I can't imagine spending that much on a hotel room. Though I would if I had the money hahaha

I have stayed at Caribbean Beach, Pop century and Saratoga Springs. I found the bus service convenient at each. You might wait 5-10 for a bus to come and from there's it's a 5-15 minute bus ride. I love not having to drive, worry about directions, traffic etc so I gladly take the Disney busses to and from the parks.

@kpc324: Are you going to Disneyland or Disney World? If it is Disneyland...I would be more inclined to get a hotel across the street and walk it over. We have done this two years at a hotel just a simple walk across. We also had a stay at Paradise Pier which was nice. Oh and for one day we stayed at a Marriott (2 loooong blocks away-too far with a 2 year old) and the DL/Marriott shuttle was horrible. Added at least an hour waiting. I responded in previous posts above with DW in mind. DL has no Magic Band and different systems than DW.

We stayed at Saratoga Springs before kids (no dining package) and although the other Disney "benefits" were great the actual hotel room itself wasn't that great. And bc we didn't have dining package and no car, we were limited to whatever hotel and Disney food that they offered.

My husband is a huge Hilton member so now we just use our Hilton points to stay at the Hilton "on" Disney property. We've stayed at the Bonnet Resort and the Waldorf Astoria for free. The rooms were better especially at Waldorf They have a pretty regular shuttle to all the parks and most of the time, we didn't have to fold the stroller bc they just rolled it straight onto bus. Hilton also has character dining on one morning.

@misolee: oh good to know about Hilton! I didn't even know there was a WA down there!

@Anagram: We did the split by checking out of one place and putting our bags in the car before park hours (morning). Then at the end of a short park hours day (or was it a long hours park hours day that we wanted to just split up? can't remember right now) we just went straight to our new hotel instead of back to our old. It was seamless. You can even have your luggage sent directly via Disney but we preferred to keep everything with us. We moved from All Star Movies to Art of Animation. Magic Bands were unaffected except that we got two sets (hooray) and I read that there are limits on times you can make purchases in the park before checkout if you want delivery.
I am a pro packer so picking up and moving is not a struggle for us. I did this with a five year old but have also done it in the past too. This is the first time I went Disney to Disney.

I went in college (with my family) ... we stayed off property, but our resort had a free shuttle.

Disneyland or Disneyworld? I highly recommend staying on Disneyland property or heading to the beach. Do NOT stay in any value-type property around Disneyland. Its ridiculously gang and crime infested, oddly enough.

Hi! I'm new to the site, saw this post and I had to comment

There is no question that staying off property is cheaper buuuuttt...

We went to Disneyworld this year from Sept 8-Sept 17th... We got free dining and stayed in a cabin in Fort Wilderness. DD was just shy of her 3rd bday, turned 3 on Sept 16th so she was free! It was an absolutely magical trip.

PROS:
-The crowds were not an issue, at all!
-The free dining was great and the portions are huge
-Fort Wilderness is gorgeous and the cabin with a kitchen was a great resource, we ordered in groceries and ate breakfast every morning in out room.
-DD loved the boat ride to the magic kingdom
-Outside Bus service (to other parks) was fast and efficient 95% of the time
-We got a golf cart to explore the property and get to the bus and boat quickly(a must!!!)

CONS
-It was hot... like beyond hot, especially at animal kingdom we ate lots of ice and drank coconut water to hydrate
-The golf cart is pricey in my opinion, and there is an internal bus system but it was slower from what I heard.
-mosquitos were bad near the boats but they do provide bug repellent
-the bus service from Disney Springs was awful... We almost missed the bus to the airport because FOUR buses drove past without stopping. but an amazing Disney employee arranged for an immediate shuttle to get us back to the resort in time.

I would 100% stay at Fort Wilderness again

@kpc324: You are so welcome!

The dining plan gives you 1 Quick service credit, 1 Table service credit, 1 snack credit for every night you stay, per person. The portions are so big you'd be okay just with that probably. but we didn't know about the portion sizes before going lol

I would still do a grocery order to do fruit, veggies and toast but we had so many leftovers.

For instance, there is a space themed restaurant in Magic Kingdom - a quarter chicken dinner equaled 1 quick service credit - it included a drink, the meal (which was huge) AND dessert!

honestly I'm so grateful there was so much walking lol

@Anagram: Yes so when you are facing the dock where the boat is, there is tons of parking to the right (near the outpost) for the golf carts. We decorated our cart with a Canadian flag and leis so we knew which one was ours

Dittos for the buses to go outside the resort.

It was awesome, we just whipped wherever we needed to go and there was golf cart parking... (you can only park and drive regular cars in certain spots)

@Anagram: It was pricey (in Canadian dollars LOL), but honestly SO fun. It was convenient to strap the stroller to the back of the cart too and DD rode up front

We can't wait to go back.