We planned a trip at Christmas time in 20 days. So you have PLENTLY of time in my opinion. The crowds were not bad (we went 3 weeks before Christmas). I really enjoyed POR-FQ at Christmas, the decorations were all done in Mardi Gras colors and it was very vibrant.
I also thought Grand Floridian looked gorgeaous with all the poinsettias.
I'm in the minority since I'm not a fan of Wilderness Lodge. It is just to dark and the native indian decor is lost on me. It is very pretty at Christmas time, but I was glad I made the switch from WL to Port Orleans - FQ.
Resorts I would *not* reccomened at Christmas:
1. Animal Kingdom Lodge - unless you like non traditional Christmas decor.
2. Carribean Beach - I'm not a fan of this resort anyway, but I thought the Christmas decorations were Tacky.
3. Coronado Springs - same as CB
4. Contemporary - not a whole lot of decorations - but w/a tower room it would be cool.
5. Pop - just a bad idea all around
Resorts I would Reccomened:
1. Yacht Club - I just loved this resort with the dark wood and the bright poinsettia decorations. There is a HUGE model train set in the lobby that your kids will love. The tree is very large with some traditional ornaments and then also some large sail boats.
2. Beach Club - PERFECT in my opinion. Bright colors, traditional decorations, chocolate carousel, decorations EVERYWHERE.
3. Polynesian - Christmas in the tropics - no huge Christmas tree but lots of decorations.
4. Grand Floridian - the flag ship resort. The decorations are beautiful here.
5. Port Orleans Riverside or French Quarter - Very well done. The decorations are a bit on the traditional side but also reflect Lousiana. No big trees.
~Amanda