My (now) husband and I stayed in Jackie's Cave House for our honeymoon. It was everything we were looking for and more. Jackie coordinated our transportation to and from the airport, which made life so much easier. I highly recommend you pay the extra fee for this! The home looks just as it does in the pictures. It was very spacious for two people. Waking up to the view every day was amazing! We used the private jacuzzi and terrace every day! We bought a glass of wine and enjoyed conversations as the sun came down.
Jackie goes above and beyond with communication and responds within the hour. She answered every and all questions we had. She met us in person when we arrived to show us around the house and gifted us beer. Also, she suggested activities, such as the catamaran, which was one of our favorite parts.
As many other reviews mention, it does get crowded during busy season (we stayed in July). Sunset hours cause a bit of people traffic as you try to walk up or down the stairs. All you need to do is say excuse me and they will move by! Also, note that there is no A/C, but the fans kept us cool at night.
If you are looking for a one of a kind experience in Santorini, this is where you need to stay! Oia is the most beautiful part of the island, you have to stay here!!