First things first: STAY AT THE DEMETER CAVE HOUSE in Pyrgos. Don't stay in Fira/Oia/Imervogli.
Pyrgos is a hidden gem. It's quiet, authentic (the locals still live here) but still has everything you'd want on holiday. Restaurants, bars, easy access to everywhere else on the island. We ate at Penelope's, had drinks at Franco's, got lost in the alleys and watched the sunsets. We hiked from Fira to Oia (fun to do for the views) and we did not think anywhere along the way had the same charm as Pyrgos.
The Demeter Cave House in itself is perfect. A modern reno in an ancient cave house has a great feeling, comfort and all the amenities you'd need. A small kitchen, nice seating area with a TV, a comfy bedroom and a BIG bathroom with double sink and double shower. We immediately felt at home in the cave house to the point where I think I could happily live there. The rooftop is accessed by a 30s (max) walk around the corner and is spacious, has some of the best views in Pyrgos. Perfectly perched between 3 churches and with views to the Ocean, it's a great way to see the sunset without any crowds. People in Pyrgos will hike up a few levels above the cave house to take the same pics you are taking. You always feel like you are in your private space though and are never really out in the open. Oh and the private yard and hot tub/plunge pool is very private (someone would have to work very hard to see you in there). Basically the perfect house.
Next is the host Andrew. Andrew is one of the kindest and most generous people we've ever met as an airbnb host or in general. Great communication before we arrived in addition to the great app which makes your stay in Santorini easy. Follow the recommendations and you'll have a great time. He arranged transfers for us, a boat trip, last minute dinner reservations, dropped us off at the beach and dinner, took us up to a viewpoint, breakfast. Basically everything that a person doesn't need to do, he did and it made our stay really special. We have since moved on to a hotel in Paros and the difference in help and service is striking.
I will be telling absolutely everyone I know to stay at the Demeter Cave House. Best accomodation, best location in Santorini, best host. Thanks Andrew from Yianni and Julie❤️