Cliff Side Suites is a chic and upscale boutique option on the caldera in Firostefani Village, which looks similar to neighboring Fira, but is less crowded since it’s farther from the cruise port. The hotel’s whitewashed buildings and 24 cave-style rooms and suites certainly look a lot like what the neighboring hotels offer, but the finish here is noticeably high quality and modern. The small outdoor pool and adjacent bar serve as the main social hub; it’s also where free hot breakfast is served. There are two whirlpools, though they don’t overlook the caldera and the water isn’t heated. Note that the hotel isn’t well signed and can be hard to find. Look for a hidden set of steps near Wild Ginger sushi restaurant and make your way down. For something similar that’s closer to Fira, check rates at Aria Suites Hotel.
Caldera views and peace and quiet
Cliff Side Suites is a boutique hotel with big views and small public places. It’s located down a steep flight of gray-painted steps and the small hotel is spread out over the cliff that drops dramatically in to the Aegean Sea. As is the island’s custom, the architecture here consists of smooth whitewashed walls and cave-style interiors with few windows, but lots of sun decks and terraces. White wicker chairs and marble-topped tables look chic with white parasols. Kids are allowed here, but there are many, many steps and most of the guests are honeymooners. Guests do gather by the small pool, since that’s where breakfast is served and the pool bar offers drinks and meals until sunset. After the sun goes down, the photoshoots are over and mostly everyone goes to bed for the night.
On the caldera in Firostefani Village
Firostefani Village is adjacent to the more well-known (and more crowded) village of Fira. It’s about a 20-minute walk along the caldera between the two cliff-hugging villages, but it will likely take longer as you stop to admire the Aegean Sea views, shop at the unending boutique and souvenir stores, and eat. Further out, it’s a 20-minute drive to Santo Wines Winery. Expect a 25-minute drive north to Oia and Amoudi Bay. Red Beach is about a 30-minute drive. Bus rides take about the same time as driving. It’s about a 10-minute drive from the ferry’s cable cars and 15 minutes to Santorini Airport.
Cliff Side Suites is difficult to find and not well-signed. It’s easier to look for Ginger Sushi Lounge, then locate a hidden set of stairs that leads down the caldera. There, you’ll find the front entrance to Cliff Side Suites. As for parking, cars can’t access the entrance of the hotel, but the public parking lot and bus stop is much closer in Firostefani than it is in Fira (you can forget about parking at all in Oia.)
Chic cave-style rooms and suites with a modern finish and some kitchenettes
Cliff Side Suites offers an excellent selection of cave-style rooms and suites, all with gorgeous caldera views from private or semi-private furnished terraces. Decor is decidedly upscale (which can’t be said of all cave-style rooms on Santorini at this price point) and include bright white walls and sheer white curtains. Soothing gray tones in armchairs and bed runners look modern, as do the matching white reading lamps next to the beds. All units come with a flat-screen TV and satellite channels, free Wi-Fi, minibar with cold drinks, air-conditioning, and safes. Some of the rooms have a kitchenette, but this must be requested when booking. Suites upgrade to more space with a spacious living room and built-in sofa, plus armchairs and framed wooden mirrors to reflect light.  Lovely bathrooms feature a cave-style shower. Robes, Oliva toiletries, and hairdryers are provided.
Delicious hot breakfast, small outdoor pool, pool bar, and two unheated whirlpools
Features here are upscale, but there are a few qualifiers. Rates come with a free hot breakfast buffet that includes American items like eggs and bacon, along with Greek yogurt and pastries. Guests can then order from a small menu of food and drink items by the pool from lunch until sunset. The pool area has gorgeous caldera views and a row of chairs set in front of a long counter for enjoying the sunset with a cocktail. The pool itself is quite small, and it’s not heated. There are two additional whirlpools, but they aren’t heated and don’t face the caldera. Wi-Fi is free throughout the property. Staff is available to assist with luggage, though there is no parking at the hotel.