I would highly recommend staying in Imerovigli, especially after braving the crowds of Fira and Firostefani. This villa is right on the crest of the caldera so the views from the huge deck are amazing - you can see both the caldera and the slope side. The house itself is a traditional cave style (the separate bedroom has no windows) which I was not expecting but really enjoyed. The main walking path is just below the deck so you do see people walking by (not a lot on this part of the path) which at first bothered us a little but then we started to enjoy listening to the conversation and laughter. For a crowded area, we felt spoiled being on such a huge lot with ample parking. Tips for the sunset viewing - we braved the crowds at Oia one night but found the sunsets around the villa were better with no crowds at all. Either walk to the second church on the path in the heart of Imerovigli for an unobstructed view (Oia in the distance but low) or walk down the path 50 meters or so just below the church (Skaros Rock will be set just below the sunset).