Could anyone recommend a good hotel in Oia? I have researched about three dozen so far and nothing stands out. I am looking for something in the village with a nice pool and am comfortable with $300 - $350 US per night.
Check Olympic Villas, Rimida Villas, Laokasti Villas, Strogili Houses, Anemomilos Hotel and Oia's Sunset Hotel. Also, be advised that there's a very nice public-access pool in Oia that's free if you buy food and/or drinks, so it would be possible to find accommodations without a pool and still be able to swim: www.lioyerma.gr
Bruce we could guess at how do-able your request is, if you'd share the Dates of your visit ... May is far different from July, not only in temperature but in prices.
We are looking at late August or early September. There may be fewer people there in early September (relatively speaking), but August should be a bit warmer. Since the original post, we have decided to increase our price range for this special stay and are leaning toward Oia Suites which would be just under $400 US/night. That is a 10-15 minute walk outside Oia, but there is a bus stop right at the door to go into Oia or Fira, and with parking available it would be handy to get away to other parts of the island.
Well I've only stayed at Villa Galinia in Akrotiri. It was great, nice pool as well. Some friends stayed at Anemoessa Villa, it was exquisite! You could also check out Maria's Place, I was looking to stay there but there weren't any rooms available the dates I wanted.