Not quite sure if the 5 star designation is very accurate; haven't looked at this particular property, but I've looked at a LOT of places in Oia for this summer when my family is doing a four night stay and many of them really stretch to get their 4 or 5 star ratings, based upon the pictures and description of service. ETA #2: Ok, I felt stupid making unsubstantiated, generalized remarks, so I looked. This place looks like a solid 4.5 star and is a bargain for what you're paying, based upon normal 4-5* prices for the area.

We ended up getting something that works excellently for us as family of seven: Bluedome Cavehouse on Airbnb. We're paying $319.25 a/i per night for a three bedroom house (with beds for seven) with an absolutely unbeatable view and which is comfortable enough and looks quite charming. Not five star, but certainly an unbeatable location and price.

ETA: Not at all meaning to knock your contribution. Oia/Santorini is a very eclectic accommodations market and every little bit of info helps, both yours and mine. I've never used Airbnb before, but I'm VERY glad I turned to this unexpected source (we're mostly staying at Park Hyatts and Starwoods otherwise) on this trip. I'm sure a more typical couple traveling will appreciate the 5 star deal.