Our stay in Oia was made so warm and homely, thanks to the two Marias - John's mom and girlfriend. We couldn't meet John as he was away on military duty, but the two Marias were so welcoming and gracious. Even though we arrived much earlier than the check-in time, the two Marias made sure we didn't have to wait too long, and made the room ready just a short while after the previous guests checked out, and yes it was clean!! :)
Though the rooms are cozy, and the bathroom a bit too small than I'd like, it was a perfect stay and gave us the best of Oia that did cost an arm and a leg! The two grocery shops are within 4 mins of walking, so you can grab a bottle of beer or some wine.
Tip : Try the shop behind the villa on the main road, NOT the marble road.
TAs suggested by other travelers, try to get a room with Caldera room across the church.
There is rooftop seating and other open tables all around the villas, so you can enjoy the sunset or breakfast away from the tourists. And while you are doing that, please ask Maria junior to make you a Greek frappe - it was heavenly and one of the best frappes I had on my entire trip to Greece!!!! :)
Thank you so much Marias for making our staying so lovely, and John for hosting us.