We wanted to experience a Cave house so we signed up for this place and it was a good experience with gorgeous views of the Caldera sunrises (didn't get to the sunsets, which were overly hyped). This place had 2 bedroom & 2 baths (albeit compact) was quite sufficient for the 4 of us, it also had a nice sitting room and a porch in the front. Kitchen was well furnished but I wish it had a few more amenities like a cutting board, cutlery.
We had asked to be picked up at the airport and shared a mini-bus with a few others who all traveled on our flight from Athens. Each (family) party had to pay 30 Euros (irrespective of size), which was fine for us but others may have objected. In retrospect, I wish I had rented a car at the airport.
Being the off-season (post Christmas, pre NY) very few places were open in Oia, so we had only a few dining options without going to Fira. But we did discover Roka a very nice restaurant which was close by (Open 1:30 PM for lunch, not sure their times for dinner). There was one place at the bus-stand that charged too much for what was offered. Looks like most places are run by an "extended family" of enterprising Albanians incl. Taxi service, cafe, bus service, house rentals....