We have stayed on and off site. Now that we are a family of 5 off site is the only choice for us!!
Pro:
*tons of space to spread out(for us everyone has their own bedroom because we choose a 6bdrm)
*can enjoy the pool/hot tub while the kids are asleep
*we have our own car and do not have to wait in long lines and be crammed into public transportation with hot, sweaty and crabby families.
*ability to cook your own meals if you want(we pretty much ate out the entire trip, but it was nice to have fresh fruit and other items and access to the full kitchen)
*If you pick the right house you have private pool/hot tub and a resort pool with waterslide. You only get a waterslide at WDW if you stay at a deluxe or mod.
*better than deluxe accommodations for mod pricing
*If you pick the right house you are just as close to the park as the values and even some mods.
*If you pick the right house the kids get to sleep in an amazing themed room. Our last house my dd got her own princess bedroom, there was a toy story room and a mickey room. The kids went crazy for them.
Cons:
Still can't find any
Some will say:
* EMH(we avoid that park)
*not having public transportation
* and the ever popular "disney bubble". I don't feel any less magical or inside the bubble off site.
*early booking, which I can see that, but you can book one night at a hotel on site and not use it to get that perk for your whole trip. Some find that price worth it for the early booking, some do not. Our last trip we had every ADR we wanted without it, but with the new FP+ it is something we are considering for our next trip.
I would avoid CL and stick with VRBO. If you go with Windsor Hills( a beautifu community very close to the parks) they have their own website too with more options!