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Ask your vet - usually the vet techs (the younger kids) in the vet's office do pet sitting to make some extra money.
The cost varies where you live (here in the land of everything being more expensive, it's more like $20 a visit) but it works out great because they not only care, they already know your pet because they're from your vet's office, and if something like your dog's eye thing happens, they know enough to bring him in to be treated.
They also are able to give meds if your pet needs them.
I did it for years and it worked out great, until my cat needed multiple meds and other care three times a day - at that point I had no choice but to medically board him at the vet's office...and (I'm lucky, I know) having a good, long-term relationship with my vet who adores my cat, she visited him and checked on him herself a few times a day.
The other thing you can check is privately-run pet hotels that take in a limited number of pets - I never used them, but I found a few in my area where they treat the pets really well, take them out and play with them a few times a day, etc.
But without question if you can figure out the pet setting thing, the least traumatic way for your pet is to leave him at home where he's comfortable and happy, and have someone come to your house.
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