The house was tastefully designed and very clean. Communication went great. Dimitra was extremely helpful from the beginning and during our stay. The house has everything you need. One problem we had with the house is that it has Zero windows. Meaning no natural light. If you shut the door, it's an absolute darkness. The view is amazing but the only way you could see it was going to the patio which was located on the rooftop. During the day was way too warm to sit outside so we ended up paying for the view but sitting in the house and not being able to enjoy. That was a bummer as most houses close by had large big windows.
The internet didn't work at all. We asked the host twice to get it fixed but nothing happened. It was a bummer because we wanted to search for the area and what to do but was not able to get anything done. Oh, and no cellphone service in the cave house.
As far as transportation the host highly recommended us to arrange it for us. It cost us €40 but we realized that there is a very nice city bus from the airport to Oia for only €1.5
The arrangement the host did was pretty much a lady holding a sign at the airport with our names and asked us to get on a car, the driver had no idea where we were going and no English so We got a bit nervous. I ended up calling the host and have him talk to the driver. The driver was a random local guy. If I go back, I wouldn't ask for transportation arrangements. Airport was tiny and several taxi waiting at the door so no need to spend €40 for a random driver.
We used the local bus during our stay to see other areas. We got to speak to few other guests at the restaurants. It seems like most of the places in Oia with the same price range offered a complimentary transportation from/to airport. Our airbnb in Fira also had complimentary transportation.