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My dog is an indoor only kinda guy, but I've had friends do various things...

There are beds that have some sort of cooling system built in them. The one I saw in person had gel in it, but I've heard of some with fans or water beds.

Outdoor misting fans are kinda expensive, but relatively cheap compared to a heat stroke emergency vet appointment.

At work we treat over-heated dogs with ice packs under their bellies. If your dogs learn to like it, they might appreciate some ice packs to lay on? Hopefully they're not chewers- even ice cubes break teeth.

My dog has a jacket by Ruff Wear that you soak with water and it cools as it evaporates. He loves it.