Absolutely stay on WDW property. We have been 6 times and the last time stayed at the Carribean. The first 5 times we stayed outside the park, never again! We are planning to go again next Nov and have already booked at the Carribean. The thing that most impressed me was the transportation system - it is great. There are always plenty of buses and the timing is perfect. Plus you get a lot of extas staying at WDW, free package return to your room, early entry, guarenteed admission, etc. It is really worth it!

Our first time to Disney with small children we stayed at the Polynesian. I thought it was worth the added expense to be close to all the Disney properties.The transportation system in Disney is great!We were able to get back and forth from all the attractions to our room quickly.

Have been to WDW in 87,93, and 96. Have never stayed on property, but agree it would be more convenient with kids. Also, get the "Unofficial Guide to WDW", it has A LOT of info you won't find in official publications. It is especially important to follow their touring advice at busy times - May is a fairly busy month. The 98 edition of the Unofficial Guide just came out - make sure you get that and not a leftover older edition. I've always gone in October and found it worth it - even though we had to take the kids out of school. If money is a concern, we've stayed in decent, but not luxurious properties within a 10-15 minute drive for $30-35 / night. Email me directly if you would like more info. Have a great time.

Definitely stay on the property for all the advantages listed by previous messages. We did it both ways when traveling with small children on a budget. Employees on Disney property are extremely helpful and buses run on time. Purchase The Unofficial Guide to Walt Disney World and follow the advise. It will save you hours of waiting in line and wear and tear on you and the kids.