If you plan on staying on Disney property, stay off site the first night. Why pay the big bucks when you are arriving later and cannot take full advantage of the benefits.
Staying at a Disney property can be pricey. I have looked into staying on property and for our family it doesn't work even with the dining plan and discounts they give. I will share my experiences and future plans with you. The first time I ever went to Disney World was with my family when I was a child. We stayed in hotels throughout the week. We got free breakfast and a pool. We were kids so we were happy with whatever. The downside is that it didn't have a shuttle service.
The next two times we went, my husband, daughter, and I stayed in a Villa at Summer Bay resort in Clermont. It offers complimentary transportation and tons of activities including water sports on their own lake. Visit Summer Bay Resort to learn more. We got an incredible discount because we were part of the Armed Forces Vacation Club (AFVC) We payed a total of 379.00 for 7 nights before taxes. I absolutely loved the villa. It was clean and spacious with 2 bedrooms and 2 bathrooms. It had a full kitchen and had great views. I felt very safe there with a gated entrance to the resort. I loved all the activities and the other amenities that came along with it. We even went to shades of green at Disney to score some deep discounted tickets for the husband.