In November, we did 2 nights on-site at All Star Music than moved for 4 nights to Cypress Pointe Grand Villas. All Star was fun but everything was such a hike - we were in Rock Inn and going to the Food Court, catching the bus, going to watch a movie at the main pool - all were a long hike after being at Disney all day. It was heaven to move to Cypress Pointe, we parked a few feet from the entrance to our condo unit, went out the back door and there was a nice pool with a huge hot tub! I find it shocking that Disney does not have hot tubs at all of their resorts
- with all the walking and standing one does there, you need a hot tub at the end of the day to relax in. I also loved having the laundry in the unit and just having lots of space to spread out.
We are returning to Disney again this November with my best friend and her family, we are doing 2 nights on-site at Pop (my friend is huge Disney fan so I thought she would like a couple of nights on-site) then we are moving to the Grand Beach Resort in a 3 bed/3 bath condo for 7 nights.
I agree with the previous poster that you should stay on-site first then move to an off-site condo. The off-site condos usually have the in-suite laundry
and just more space to spread out which is very beneficial once you start shopping.
To be honest, having experienced staying on-site at Value Disney resorts, I much prefer off-site in a condo. We have stayed at Grand Beach Resort, Sheraton Vistana Resort, Cypress Pointe Grand Villas (all within 5 minutes drive of Disney) and Villas at Fortune Place in Kissimmee which was about 25 minutes of driving. I like having a rental car and all the freedom it gives you to shop at the Disney Outlet store, go grocery shopping and just be in air conditioning. We also like to do SeaWorld and Universal or catch a ball game down in Tampa (we are hoping to catch a hockey game this November) so being on-site 24/7 at Disney is not a perk for us.