Has anyone been to both of these places? Is one better than the other? Is there similar accomodation that's better? Thanks!

They're both good choices. The biggest difference is that Strogili has a pool. Both have excellent caldera views. Neither has a view of the sunset. Strogili is about a 15-minute walk from the village square. OOH is 5-10 minutes' walk to the square but on the other side of the village. Part of the walk from Strogili is along the main road with lots of traffic on a narrow street with no sidewalks.

Also check out Lena's House, Lucky Houses, Rimida Villas, Lauda Hotel and Filotera Villas.

Thanks! Do any of the places you mention have a sunset view?

No. Your choices for a sunset view are Esperas, Fanari Villas, Golden Sunset Villas, Oia Castle Hotel and Marizan Villas.

Thanks for the info brotherleelove.

I've got my plans a little more settled now, and am deciding between Old Oia Houses and Marizan Villas. Marizan Villas is more expensive, so I want to know if it's worth the more money. I know one of the best things to see in Oia is the sunset! Is the sunset view walkable from Old Oia Houses? Thanks so much!

Oia is small. OOH is only about 5 minutes' walk from the sunset vista point.

I'd rather have a room with a caldera view. It lasts all day but the sunset only lasts a short time.

One observation I made last June about the location of Marizan Villas: It gets very windy on that end of Oia around sunset when the air is cooling.

Well, if I were you, I would also check Imerovigli Village. It is located close to the capital, Fira, and most of the hotels built there have a view to the volcano and the caldera which is amazing. Moreover, Imerovigli is said to be the best place for sunset watching and as BBL said, it doesn’t last much, so you should look for a caldera or sea view room rather than sunset view. Go to Oia, at the castle, on sunset time, early enough to find a good place from where you will enjoy the best sunset view you have ever had!

Thank you! I will look into Imerovigli Village. I fell in love with Oia after watching "Sisterhood of the Traveling Pants" Is the caldera view from OOH similar to the caldera view from Imerovigli Village?

The view from Imerovigli is actually better, as long as your sunset view isn't blocked by Skaros Rock, since it's higher up on the cliff and overlooks all of Oia from a distance when you're facing towards the sunset. The 'downside' of Imerovigli is that there are very few shops and restaurants there, and if you're on foot and in Fira for some dining or clubbing and have to walk back to your hotel it's all uphill. Some of the hotels in Imerovigli are actually even further out from Fira, so be sure you know where yours is actually located. Of course you can take the bus or a taxi but the later it gets the more difficult that becomes.

Poor sentence structure may have confused you. It's Imerovigli that's higher up on the cliff, not Skaros Rock. But if you're between Skaros Rock and Fira your view westward towards the sunset and Oia may be blocked depending on the hotel and whether or not it's higher up than Skaros Rock.

Are there any apartment-hotels like OOH in Imerovigli, that you'd reccommend?

The only one I know of with the view you want in the same general price range as OOH is Gizis Apartments. http://www.gizishotel-santorini.com/rates.php

I also want to let you know that Gizis Apartments is one of those that is even further out from Fira on the way to Oia. But have a look at the panorama shot of the caldera on the website, the view is amazing.