Santorini Lodging recommendations please

In Oia check Ifestio Villas. They have 2- and 3 bedroom units but no pool. There is a very nice public access pool in Oia: www.lioyerma.gr

We had a lovely experience at Dana Villas in Firostefani in June 2016. I'm not sure of current prices, but it has a great pool and a very good buffet breakfast. We would go back.

Hi Dale! Welcome to Greece, the land of small rooms ... almost nowhere in Greece will you find a room for 5! I realize, coming from the Land of Red Roof Inn, etc, many in US are accustomed to big rooms w 2 queen-size beds, by the pool. And at $50p.p. In USA -- and when people complain to me that they can't find such deals abroad, I remind them: those queen beds by the pool are just off Route 70 in Ohio ... and here you are on a Famous Isle in Greece!

Your challenge is tough even in FIrostephani or Fira, and forget Oia!! Particular sticking points are CALDERA view from ROOM.. also pool request. I'm v. familiar FIrostephani, looked over the 49hotels available for your 3 nites (BTW, you don't make it clear if that's 3 nights or 4. I took it as 3 x 500 = $1500). BTW, sometimes lowest quotes on Booking.com are NON-refundable (& yu must pony up deposit). Since u are looking far ahead, pay the extra 10% or so and take the fully-refundable, and Pay-when-there price. Here's what I can recommend -- all on the cliffside, all w inland side handily just off the main road near the bus stop to Oia, and all walkable to Fira Town museums, shopping, clubs etc, in 15 minn. --based on Booking.com availability Sept 12-13-14:
• SUNSET HOTEL - $1213/3 nights - No pool, rooms don't have caldera view BUT there's a large common rooftop terrace with lovely wicker settees and a Stunning view! I know because I sat there one sunset w. friends and enjoyed great bottle of Santorini white wine (I'm not a white wine fan, but Santorini's is justly famous, dry, w a citrusy afterglow)
• AGNADEMA APARTMENTS -- About $1689, 1 apt & 1 room; some have views -- Lovely Pool area w seating & caldera view.
• HOTEL MYLOS - about $1500 3 nights, no pool, caldera v iew from most/all rooms
• AEGALI HOUSE -- $ about 2,000 at refundable rates - 2 superior doubles, w. extra bed in larger one, for 3rd person.
I don't know this one, but it's promising -- Rooms say"sea view" which usually means eastward, not caldera, but text seems to promise view of caldera. location near the above.

I didn't find anything that promising in Fira Town, except for places built way down on wall of the cliff, requiring vertiginous descents and arduous ascents on 100+ steps.

thanks everyone I actually found just what I want for just barely over our $500/night budget.. http://luckyhomes-oia.com/house01.htm

Good choice in a very good location.

Congratulations ... sources like that are often more successful for group sizes like yours...