Old Key West...

OKW has resort mugs for sale, yes. There is a spot behind the hospitality house where they can be filled. I forget the name of the place...
 
It's normally in the main resort shop, it'll be Conch Flats General Store in OKW. There are usually refill machines at the main shop and some of the pools as well.
 


Are resort mugs at OKW different from others?

will it matter if we stay at a DVC?

Disney currently offers the refillable mug program at all their WDW resorts. You can purchase them at your resort (or get them free with the dining plan) and refill them at your resort. They expire at the end of your stay at that resort.
 


They can be filled at Goods To Go, which is across from the main pool, behind the Hospitality House. We don't usually find them very practical for OKW due to the layout of the resort unless you plan on staying near or heading up to the Hospitality House a lot. We usually resort to buying bottled beverages to keep in our resort fridge.
 

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