We had our family reunion at Villa Santorini during a brutal cold snap and so cannot comment on any of the outdoor-ness but the house itself was lovely! The wood burning stoves + central heat kept the whole house toasty warm in spite of -15 wind chill. The kitchen is extremely well equipped (magically so, actually, for a rental). Hilary was super-helpful and immediately responsive to any questions we had. The house has been very thoughtfully supplied with everything you need - from extra beach towels to board games - for a perfect vacation. The whole house is a top-notch renovation - high end appliances, fixtures, media, etc. Classy all the way.
Two things to keep in mind if you are thinking of booking this property:
1. Although the house absolutely can sleep 30 people, it might not be in an ideal configuration. There are two HUGE "view" bedrooms, and then 5 small bedrooms. If the grownups in your group want the view bedrooms to themselves, you'll be giving up a fair bit of supplemental sleeping space. If you are willing to give up a master bedroom to the kids, you can accommodate a lot more sleeping bodies. You could easily add 2 queen airbeds to each of the king bed master suites, but none of the smaller bedrooms can accommodate an airbed. One has 4 twin beds, the others all sleep 2 people in queen beds. Just something to think about. We were able to put two airbeds in the media room.
2. The house has a cool, eco-friendly ozone based washing machine. It runs on cold water only, no detergent. Great for the planet, great for light wash needs. Not great for anything truly dirty. Spaghetti sauce and grease stains did not come out in the wash. If you are traveling with kids you will want to pack heavily enough to not need to do laundry, or you'll want to factor in a laundromat visit so you can blast detergent, bleach and hot water through your baby food disasters. Of course if you come in the summer the kids can wear a bathing suit all week and there won't be any laundry!