We grabbed a a quick week in Oia at the end of July/early August and it was a delight.
The island itself is very picturesque and Oia in particular...also Imerovigli nearby.
We stayed at Casa Francesca and despite a 7 hour outbound delay and arriving at 11pm instead of lunchtime, we still arrived to find the very helpful and charming staff still there to greet us, let us into our accommodation and show us a couple of places we might grab a quick bite in Oia. The manageress, Andrea, then came back as agreed the following morning to take us through what we might like to do on the island...not in any attempt to sell us tours, but because of her obvious passion for the island. 10/10 plus for the staff ...very charming.
Beyond that the room was cleaned daily with fresh towels pretty much daily, usually arranged into a series of towel sculptures on the bed, including two swans forming a love heart - sweet.. For reasonably priced accommodation in this typically premium priced resort, the welcome and service was exceptional.
The rooms also were very nice ...modestly furnished but charming...and with sea views over farmlands, rather than the caldera, a good sunny balcony with sun loungers, and with the caldera views an mere 100 meters away from the main avenue through the town
We swam and ate a lot in the Amoudi Bay area, which is below the town (250 steps!). Swimming is off the rocks and it pays to get their early to bag one of the more comfortable spots, but then the snorkeling is great and there is an island to swim to/ around with a tiny church on it. lovely...but not for you if you want sandy beaches. We didn't.
The seafood at the tavernas there was excellent - try the seafood spaghetti or the grilled prawns at the last taverna from the base of the town steps walking towards the little island. Memorable, though they are all good. Trevor McDonald was also there one lunchtime filming a travelogue on the island. This little area has a reputation for great seafood, though the food throughout Oia was generally very good.
So all in all we had a really lovely holiday which reminded us just how relaxing a holiday in Greece is.
You can see some of my shots of the island at http://www.pbase.com/paulwin/santorini_2010
Our thanks again to Casa Francesca, Andrea and the other staff whose names I'm afraid to say I've forgotten, In short this accommodation makes Oia affordable and is of a good standard, and enhanced by lovely staff.
Incidentally Andrea said her favourite months in Oia were May and September/October - less busy from day trippers coming to see this picturesque town and still pleasantly warm.
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC