My mom, who is in her mid 70’s and has always wanted to go to Disney World, has decided that she wants to take her two daughters, I’m one of them, and her two grandaughters, one is my child, on a girls trip to WDW. I love this idea, of course, but know that the planning is going to be a challenge. To accomodate everyone’s schedule we will have to go in June of 2020 and Mom wants to meet with me to discuss and price the options. I want to try to get the ball rolling before I meet with her and will start with hotel options. Though we don’t have a specfic resort in mind, we do want to stay on property. (I should insert here, that while we don’t have a hotel preference at this point, I’ve always wanted to stay at the Yacht or Beach club, but I suspect that my mom will balk at the price.) Here’s my first problem: I have been able to research the DVC rental options a bit so I have a rough idea of room types and prices for 5 guests, but I’m unable to run the numbers on anything else because those dates don’t show up on the Disney site. If we want to do a DVC point rental I understand that we will need to try for that 11 months ahead, which only gives us a couple of weeks to make this decision, but I don’t want to pull the trigger without being able to compare other options. Any suggestions or insight?
Package prices for 2020 are due out on the 18th June. 
You can also run the prices for this year and use that as a guide.
here is a website for info on when rake rates are published and when historical discounts are offered
I am curious about this:
First, are these discounts generally across the board? Or do they only apply to select rooms?
And so, let’s say at 499 days out, I book a room at the Contemporary. Then, presuming they offer the same type of discount next year, can I then call up Disney on August 15 and have them retroactively apply the discount? I believe that is possible…but then, perhaps it wouldn’t apply to that specific room.
Yes, if requested WDW will retroactively apply discounts if they are still available for the resort/room class you have already booked. This is why some people prefer to go with a TA - a reputable one will be monitoring discounts and will try to snag applicable ones for their clients.
That’s the part I am unclear about. I know they will retroactively apply discounts, but it isn’t clear as to what it means to be “still available”.
Does that mean that if all rooms of the type I have already reserved have been filled up, even though the advertised discount applies to my room type, that it would no longer be considered “available”? Or, put another way, does it only apply to rooms where there is at least ONE of the same type available?
There are not always rooms in each resort, and even if there are, they don’t have them available in every category (I think this is what you are asking!). And it changes based on that availability, so if you don’t see what you want immediately, check back often. I REALLY wanted BC/YC/BWI for our last stay and just couldn’t piece together the AP discount for the days we needed. About a month before, I had a split stay at the same resort (BWI). Finally, after a month or so of daily checks, I found the standard view room for BC I was looking for for my entire stay.
Also, the AP rates aren’t always the best. Sometimes I’ve done better with MVT and, sadly, for August, the standard ‘sun and fun’ discount available to everyone is better than the AP rate. It pays to shop around - and if you have a TA - to have a very patient one who will constantly move the reservation to wherever the best deal is at the time!
That’s not QUITE what I mean. So, let me state it this way.
Let’s say I reserve a lake view room at 499 days out (full price) for a room in the Contemporary Tower. Now, let’s further say that TYPICALLY, a lake view room would be included in the discount in August for the December 8th date (picked for illustrative purposes only).
Now, let’s say that on August 14th, they announce the discount, which includes the lake view Contemporary room. But, if someone were to try to actually BOOK that room, Disney would said, “Sorry. We’re all full up. How about this lovely Garden View room instead?”
But, when I call up, I said, “I already have a lake view room. Can you please apply the discount?”
Will they said, “Sure! No problem!”
Or will they say, “I’m sorry. Because there is no availability of that room, we cannot apply the discount retroactively.”
OR, alternatively, would they have never listed the Contemporary Lake view as a room that the discount applies?
Ok, got it. They will say there is no availability. I don’t know if there is a list of what once had availability or not, but they won’t just apply a discount to a previously booked room if there is no availability showing for the discount.
Okay. Thanks.
That makes booking super early, then, a bit of a risk. You could end up stuck with a room at a much higher price, then. But, on the other hand, if you don’t book early, you risk the room you want being sold out. 
When I was discussing availability, I was referring to availability of the discount for the class of room booked, not whether that room class is available for reservations for the dates in question.
However, to sort of answer your question, I believe that if you have the room class booked and the discount applies, then they will apply it regardless of whether there are any more rooms of that type available as they are not actually re-booking (and therefore looking for room availability) but are instead just applying it to your specific reservation.
@ryan1 In my experience (including plans for this summer) Disney will apply discounts retroactively to already booked vacations. In your example, if the type of Contemporary room that you had already booked was included in the new discount offering, you can indeed call to get the new discount put on your current reservation.
We just had this experience with booking free dining (when it was rereleased in May I believe). The type of room we had booked earlier was fully booked by the time free dining was offered again, but when I called to get free dining put on our reservation - it was not a problem to change the promotion for our reservation. It took a little longer because our room type was fully booked so they had to spend more time to edit our reservation, but getting the promotion was no big deal (we still have same room class plus the bigger discount of free dining - 5 adults make the free dining discount huge for us).
The only time this wouldn’t work (again, in my experience) is if you have a room reservation that isn’t included in the promotion being offered. There have been times we have stayed at POFQ and a promotion comes up after booking that we couldn’t apply to our reservation because POFQ wasn’t included in the promotion.
That makes booking super early, then, a bit of a risk. You could end up stuck with a room at a much higher price, then. But, on the other hand, if you don’t book early, you risk the room you want being sold out.
Yes–This.
This all leads me to wonder if there is any place, like the MouseSavers page, that not only lists historical discounts, but the SPECIFICS of those historical discounts. (Which hotels were included/not included.) That could be super useful to know.
From what I have heard and read, this is not something that is available, as Disney doesn’t release the number of rooms available for any of the discounts. They also do not release specifics on any discounts. Give you an example. The parties are always Limited number of tickets, however, there is no information on the number of the tickets available. It is Disney that decides what 'Limited" means.
The discounts on rooms that I have seen, they always have somewhere in the fine print the word “Limited”.
Okay. I guess I’ll pay attention explicitly this year as to what happens in August. I’ll see what rooms are actually discounted, and hope the same will apply in 2020.
Ah. Just for the fun of it, I wanted to look at availability for December 2019 right NOW. Turns out, there is none for ANY room type at the Contemporary. Which means that come August, there wouldn’t not be any discounts offered, I’m sure. So booking early will be the only option and pay full price.
We are only doing a single night at the Contemporary, though.
This was definitely not my experience with the AP discount. I had a room booked at BWI and called to have the discount applied, but by the time I actually reached someone, the availability was gone and I was unable to get the discounted rate. I needed to keep shopping for availability.