We are going to Santorini in June. So far I have three places picked out. I am debating on splurging on a $210 cave house on Oai which is double my target budget of $100 - $120 a night but has gorgeous views and is right on the cliff below the church with the blue roof or a cute B&B in Firostefani that is $118 a night or a house in Pyrgos for $107. We are on the island for 3 nights. Any advice? I have read about dreadful crowds in Oai and Fira.
Yes, it does get crowded in Oia, but nowhere near as crowded as in Fira. There are some choices in Oia that are not so expensive and still come with the view. Check Thea Studios (make sure it's the one in Oia), Aspa Villas, Villa Kallisti, Casa Sofia and Olympic Villas. Firostefani is a good option if you want easy walking-distance access to all that Fira has to offer. Pyrgos is a lovely traditional village and you can see most of the island from there since it's at a high elevation over the sea. Oia is the most beautiful and romantic village.
Thank you so much for the suggestions. I think I am going to stay in one of the ones you suggested on Oai. I really appreciate it.
Another tip, some pensions and hotels on the non-caldera side have access to patios and outdoor seating areas on the caldera side as their owners both several properties. My wife and I booked a pension (sorry I forget the name) like this in Oia where if we wanted to sit and people watch and have a beer overlooking the caldera we just had to cross the street to to the private patio of the hotel across the street. If you are worried about money this might be a compromise for you.