Accommodations in Santorini with great sunset views

"Caldera view" refers to what you see from the top of the cliffs looking down into what's left of a once-active volcano's (Santorini) caldera. The villages with a caldera view are Fira, Firostefani, Imerovigli and Oia. For me "sea view" means a view from anywhere you can see the open sea outside the bounds of the caldera, such as the view from Perissa Beach or Kamari Beach, or from somewhere higher up the island's sloping topography and facing away from the caldera. THIS map should help you understand. "Mountain view" means just that, the view from any location that faces the mountain which separates Kamari and Perissa. "Sunset view" is obvious. It's from any location that faces west with nothing blocking the view. Only a small percentage of hotels on the cliffs have this view since most face south and not west. The sun moves northward as the season progresses, narrowing the choices even more as the months go by, but in May it shouldn't be a problem. In Imerovigli check Gizis Apartments, Prekas Apartments and Abyssanto Suites & Spa. I don't think there's anything in Oia with a sunset view within your budget but you can have a great caldera view in Oia at Thea Studios. I'm pretty sure you can see the sunset in May from the Sunset Hotel and the Hotel Mylos in Firostefani and from the Scirocco Apartments in Fira.

Thank you Lee for helping me understand that! At Oia would there be a good/somewhat private place to watch the sunset? Since we are going at the end of May I understand it will be busy and would like to avoid being completely packed in with lots of tourists/cruise people while watching the sunset. I've also read that Fira is pretty busy and touristy, do the Scirocco Apartments feel like they are in the midst of the city? Do either Imerovigli or Firostefani have the white buildings like Oia does?
Again, thank you!

It's a bit of a challenge to find someplace quiet in Oia to watch the sunset but if you walk partway down the steps to Amoudi Bay, below the crowd at the top, you can watch it in peace and quiet. Or you can walk partway down the road to Amoudi (it begins next to the post office) until you're facing west and just sit on the side of the road. If you don't mind a short trek you could walk to the trailhead for the hike to Fira (out past the desalination plant) and not only see the sunset but observe the color changes on all the buildings in Oia since you'd be above them in elevation. There are 3 restaurants with sunset views, the Ochre Wine Bistro, Kastro and Strogili. The Lioyerma Cafe/Pool has a front row seat poolside. When you're on the grounds of the Scirocco Apartments you won't be in the middle of all the village activity, you'll be down the cliff below it. I imagine there will be some foot traffic around you but not very much at all. It's quiet there. The prevailing color scheme on the island is white buildings with blue trim. You will find it everywhere.

I appreciate the response!
I think I've been able to narrow it down to Gizis Apts or Sunset Hotel. Any additional thoughts about these two? Pros or cons between them?

Gizis is a bit remote. If you stay there having a rental car at your disposal would be a very good thing. It's probably about 2 miles from Fira and it's an uphill walk back to Gizis the whole way. Of course there are buses and taxis too but a rental would be best and they're not really very expensive. The Sunset Hotel is just about 15 minutes' walk from the center of Fira. If you think you might go for one be sure to go to your local AAA office to pick up an International Driving Permit, no test or membership required, for about $20 plus a photo fee if you don't bring 2 passport photos with you. At least take the IDP with you and decide once you're there if you want to rent a car.

The Sunset Hotel is in Firostephani, and is very well situated ... as lee says u can easily walk to Fira square in 15 minutes, either on the rim path OR on a little-known lane that parallels the busy main road. Yet it's very serene by day AND evening because the cruise/tourbus crowds go only to Oia & Fira town. Hotel has only about 10-12 rooms but a nice large common roof terrace w. cushiony wicker chairs. I fondly remember spectacular sunsets there... no crowds no noise, no standing in a rim-path crowd.

I stayed at the Theoxenia Hotel in Fera on Via d'oro - with a patio and view of the ocean (caldera). There were 3 of us and I don't remember how much the room was - you may be able to find a current price on TripAdvisor or another similar site. But we all agreed that is one of the BEST hotels and views of all the hotels I have stayed in. We sat every evening on the patio with a bottle of wine, some cheese, fruit and crackers and it was so wonderful. They delivered a generous breakfast to our patio every morning at a time we chose and we started our days enjoying the caldera views. -------------------- Thanks for the comment posted below - yes, the hotel is on the main pedestrian street, but we are 3 gals in our 60s and the noise
did not bother us at all - our room was on the 3rd floor.

The Theoxenia may be a good hotel but it's far from quiet since it's right in the middle of all the fancy shops and galleries where all the cruise ship passengers congregate when they come ashore. To be fair, a standard room in May is in your budget, however, so you might want to take a look at their WEBSITE.

I'm not sure how much Sunset Hotel prices have risen, but in late may 2010, a double was €60 ... even in 2014, better than Theoxenia, I'm guessing.

We were in Santorini this past May, and most days the cloud cover conspired to foil the sunset. However, the temperature was mild, the scenery beautiful, and the food delicious. I simply encourage you not to hang the success of your visit on the sunsets, which may disappoint. That said, I would add to others' suggestions the restaurant Kyprida in Oia, where one night we had a very nice meal with sunset view, off the beaten path.