The last 2 years we saw several much lower OKW prices appear as August arrived, but very few of these were 5-nighters. If I needed a long stay I wouldn’t bet on getting a better one later.
5-night Old Key West Studio 08/01 for $262/night or 2% under median
Probably not the cheapest February price we’ll see for this room, but very few will be 4-nighters. A much more than respectable amount under median and a worthy listing.
4-night Old Key West Studio 02/10 for $297/night or 10% under median
Not a high volume room in historical data, but this is the lowest July price recorded by about $130/night. There have only been a small handful of lower listings in other times of the year.
2-night Beach Club Villas 2 Bedroom 07/25 for $728/night or 30% under median
Even though this is “just” 8% under median for September, in reality the majority of lower Poly prices don’t stray much farther below, this. Verdict: Go for it!
2-night Polynesian Villas Studio 09/11 for $374/night or 8% under median
14-night Saratoga Springs Studio 09/12 for $229/night or 2% under median
vs all September multi-night SSR listings, this one is just under median.
Will we see lower priced ones appear as time moves on? Almost certainly, likely somewhere close to a beefy several.
Once you start comparing to 4-nights or longer, that expected number drops faster than a teenager outside of a flume boat.
Let’s Limit to Long Lengths
vs >=7-night Listings
This listing is 6.5% under median vs all longer Sept stays
There have been 61 listings 7-nights or longer.
Weirdly in BOTH 2024 and 2025 there were 22 listings and exactly 11 of them were at this price point or lower.
This year there have been 17 total and 8 of them were at or below this price point.
Only 1 or 2 appeared each year any closer than this number of days out from check in.
Looking at longer stay comparisons is iffy because the numbers drop precipitously:
Number of >=
8-nights: 11 listings
9-nights: 6
10-nights: 5
This is the only September 14-nighter.
BOUGIE ALERT. There are TWO sequential Grand Flo Grand Villas that had huge drops to 46% under median. Is a rare room in the data so the median is squishy, but FWIW the rack cash rate of this room is about $3,800/night before tax. Do with it what you will.
3-night Grand Floridian Grand Villa 07/12 orig $3,013/night now $1,310/n or 46% under median
2-night Grand Floridian Grand Villa 07/15 orig $3,013/night now $1,310/n or 46% under median
This is very likely the last long SSR we’ll see for July…
6-night Saratoga Springs Studio 07/26 for $258/night or 16% under median
If you want a below median May Aulani hotel room - NOW IS THE TIME.
Almost all lower priced listings for this room show up now at 11 months and we got two tonight!
5-night Aulani Hotel/Inn 05/22 for $408/night or 11% under median
6-night Aulani Hotel/Inn 05/23 for $408/night or 11% under median
Near the bottom of recorded prices
Now is the time, now is the BEST time… 
