We had a beautiful stay in Oia. Aris' villa had a fantastic view of the caldera. Just keep in mind that you are mainly paying a premium for the private pool (with neighbours immediately on both sides) and the view, therefore if you are out doing activities each day, you may find that you can book a more affordable location without those two things.
Aris gave us a great introduction to the island and the villa and helped us with transfers from the airport and ferries. I would recommend getting some quad bikes on Santorini, they are the best and most fun way to get around. Also go to Santorini mou restaurant! It is great!