I’m probably much like you. I researched and wanted the “best” caldera view in Oia with a private dipping pool, etc etc. Then I looked at the prices (and I was there off season)! Good lord! It’s not just lodging that is expensive. You can expect to pay 10 euros for food that costs 5 euros in Athens. I settled on Pergeri apartments because of the good reviews about hospitality and it’s more than reasonable prices. I like that it’s small (only four or five apartments) and a beautiful giant (shared, but each apartment has a perimeter made by a rail or pots of flowers) balcony sea view. It was way more amazing than what I imagined!! Super big with cold fridge and fold up clothesline and pins. Upsides: clean, spacious, beautiful sunrise views, breakfast catered to your room, owners will have an ATV or scooter brought to the location for you, beautiful caldera sunset view a 5min walk away, Taverna Tasos 2 min away (very very good). Close to Oia-Thira bus line. Drawbacks: very tight shower and bathroom but it can work, and that ATV I was talking about, you’ll need it if you want to explore Oia, Thira, beaches, etc. Only Imerovigli is close enough to walk. No nearby supermarket. And speaking of that convenient bus that’s only 1.50 euros — I wouldn’t recommend taking it to Oia unless you aren’t scared of heights. You’ll be driving cliff side and pretty fast on a small winding road. Overall: totally accessible if you rent an ATV or car, which you really need to do if you want to see the island anyway, and it’s away from the crowds. Perfect for families with the couch turning into a bed. I’d definitely stay here again. So spacious, the sunrises are spectacular, and the hosts are awesome!