Our stay at Jackie's cave house was amazing! As far as views and convenience go, the location is unbeatable.
Since the house is several flights of stairs below the main street, it's super close to attractions but also tucked away enough to give you relative privacy while enjoying the insane views from the terrace.
Like the other reviews, I will say that due to the incredible location and views (you're literally under the most pictured blue domes of Santorini), the tourist/pictures situation can probably get overwhelming. We went in October and it was still a daily ordeal to get down the stairs to the house, since the path is crowded with everything from people taking regular phone selfies to brides and grooms doing full photo shoots.
BUT it's worth it. It's nothing you won't get over once you're back home on that terrace! As far as photo takers getting in your space while you're trying to sunbathe, we didn't have any issues. We just left out our hats and magazines on the chairs to convey that the terrace is a private space.
Other notes: lots of space, comfy couches, comfy bed, and lovely, amazingly gracious hostess! Jackie arranged our transfer and had someone carry our luggage from the car to the house. From check-in to check-out, everything was perfect.