This probably sounds weird, but I'm wondering if anybody knows which hotels in Oia have actual doors on the bathrooms, and preferably a shower that doesn't get the toilet wet? I am also looking for a caldera view from the room balcony, ideally with a pool, hopefully for not much more than $200/night, if that exists. Thank you! This is for a trip this May, 2013, one couple, for about 5-6 nights.

Or maybe a pool is not necessary between May 14th - 20th?

Esperas House did. However, they cave rooms which may or may not appeal to you, and lot of stairs too.

The cave rooms look great, and stairs are fine, but I think the Esperas has sunset views, not caldera views.

The restaurant with the sunset crowds is nearby. You sit on gour private balcony and look at the crowds over there.
Personally we didn't like the cave room . It was well appointed, nice bathroom but a cave, natural light only at the front entrance. Our ancestors left caves for houses for a reason.