We had a great time at Jessica's house. The location is great, within the medieval settlements of Ano Syros. Many cafes and taverns with view are nearby. The people of Ano Syros were really hospitable. Going to Hermoupolis is easy by a free minibus until 22:30, and even by feet (thought returning from there is not recommended by feet). You can also get a taxi costing about 4 euros until 24:00 o clock.
The house is great. It is made of stone so it's really cool. You can find all the necessary stuff in the kitchen. The bathroom is comfortable (care your head when going in, the passage is low). There is no air-conditioner on the room, but as I said the room is really cool from its making and its position, so it wasn't necessary at all during our stay.
The host was great. They came and took us from the port (we had no means of transport). They helped us with whatever we needed and were really communicative.