After staying in Oia 10 years ago, the prices (which were already high) have not unexpectedly risen even higher. I think the cave house we stayed at was $150/night and now about £250/night. Wow. In any case this time I had read that Imerovigli had a higher setting and therefore better sunset view than Oia. Additionally a sunset private jacuzzi would make it even more memorable, made possible (and affordable) only by the fact that there was 10% of the usual tourists and accommodations were often discounted.
I found Kasimatis to be the most affordable with the honeymoon suite at £196/night down from £250/night. Luck would have it that we were given an upgrade to the junior suite (£300/night) which had an excellent view of the world, although people did have to cross past the front of the outdoor area to get in and out of the place.
Our host was a stunning Greek woman dressed as classic Athenians would have, and very attentive and friendly to match. The breakfasts were collections of yoghurt, fruit, pastries, eggs and more.
How I miss it already.