Luckily the presence of many hotel neighbors doesn't seem to disturb the relaxing vibe at Anastasis Apartments. The 11 large, apartment-style units have individualized contemporary decor and offer private balconies and kitchenettes. A welcome plus for many travelers: Anastasis Apartments is free of Santorini's typical (and tiring) cliff steps, making it great for anyone concerned with mobility issues. While there are bars and restaurants within easy walking distance of the Anastasis, keep in mind that most other mid- to upper-mid-range venues are set up for self-catering. If you want something more than just snacks on-site, you'll have to bump it up to a higher category.

This small hotel on the island of Santorini is comprised of seven luxury villas featuring fireplaces, private verandas, and high-end decor details. Elevated atop the less crowded northern curve of the area’s caldera and having replaced its bar and restaurant with butler and room service, Aenaon Villas is set up for upscale couples searching for a private retreat. There are no children under 12 permitted. Guests interested in a less isolated experience should look at neighboring San Antonio Hotel, which is larger and has a more sociable vibe.

For those looking to escape the bustle of certain Santorini locales, the 27-room Astra Suites’ quiet cliff-side location is a well-regarded option. The hotel has remarkable views with rocky caldera cliffs at its sides, the Aegean Sea below, and bright blue skies above. Rooms have large personal terraces and fluffy bedding while outdoor spaces are sleek and modern. The mix of traditional architecture and colorful contemporary decor gives the property an elegant and relaxing vibe. However, considering the high number of stairs, Astra’s not ideal for those with mobility issues.

Located in the village of Imerovigli -- an area known for spectacular sunsets -- and built along a caldera rim, the upscale Santorini Princess has loads of outdoor seating for soaking up the scene. The hotel’s 22 spotless apartment-style suites are spacious and comfortable, and most afford superb views from private terraces. With an outdoor pool, bar, lounge, and cafe, as well as an on-site restaurant and spa, guests never need leave the hotel’s isolated location. However, multiple stairs and no elevators are a problem for those with mobility issues, and guests seeking a popping nightlife are better off checking out places directly in town like Dreams Luxury Suites.

Above Blue Suites is an excellent four-pearl choice in the quiet and scenic village of Imerovigli. The village has the same stunning caldera and Aegean Sea views as neighboring Fira (a 20-minute walk) and popular Oia (a 20-minute drive), but Imerovigli is one of the quieter spots on the cliffs. The boutique hotel offers 10 individually decorated cave-style suites and all have private or semi-private terraces that face the water. Some upgrade to indoor or outdoor whirlpools. There's a chic pool and deck lined with sun loungers -- this is where candlelit dinners can be arranged in the evenings. Free hot breakfast is delivered to rooms every morning, which feels luxurious. As a cheaper alternative with the same views and a free continental breakfast, check rates at Prekas Apartments. 

The luxurious Kapari Natural Resort is undoubtedly one of the more beautiful Cycladic-style properties in Imerovigli -- or even the island. Cream-colored rooms are sophisticated and minimalist, with built-in furniture, and many have big indoor hot tubs. An on-site restaurant also impresses with excellent food and wine, and 24-hour room service is a nice touch. The lack of a private terrace in some rooms might disappoint -- as might the tiny pool. For a similarly chic vibe with decent-size pool, check out Honeymoon Petra Villas nearby. 

One of the more chic and stylish boutique hotels in the area, the adult-only Avaton Resort also features a serene and relatively secluded position on the outskirts of Imerovigli village. Its cliff-top setting also guarantees some of the best sunset views on the island, which can be enjoyed from the infinity-edge pool and each of the 11 rooms. Also offering a restaurant and impressive spa, this hotel really does have the whole package. The only real downside is its position makes it prone to wind so alfresco dining can be an issue. Astra Suites nearby is another excellent upscale option, though it allows children. 

With only nine rooms, the 2016-opened Cocoon Suites is an upscale, adult-only property, central to the small village of Imerovigli. Aegean Sea and caldera views here are some of the best in Santorini, available from loungers on cliff-perched terraces. Chic suites have minibars, private hot tubs or plunge pools, and smartly furnished terraces where breakfasts and meals are delivered -- candle-lit terrace dinners are particularly romantic. Room amenities mostly make up for unusual setups here, which don't include a communal pool, bar, or restaurant. While Santorini's notorious steep steps here are unavoidable, the views are the reward. The Astra Suites has a pool, but the property is less private.

The 10-suite Afroessa Hotel is a great upscale option for couples looking for a quiet boutique property along the Imerovigli caldera and away from city crowds, with a little bit of history to boot. Individually decorated rooms with kitchenettes preserve authentic elements from the original site's 18th-century winery. Guests can swim in the outdoor cliff-side pool or enjoy the hotel’s two bars, though there’s no on-site restaurant. As at many other nearby hotels, guests with mobility issues need to consider the high number of stairs. All in all, it's a great value considering the caldera views, but guests should know that the reception desk is only open 12 hours a day, surprising for a four-pearl property.

The upscale San Antonio Hotel is in a secluded location far from other hotels at the narrowest point on the island of Santorini. The cliffside spot provides unobstructed views of the caldera and the Aegean Sea from its infinity pool and restaurant terrace, where a free American breakfast is served. The rooms have excellent views from their large furnished balconies too, though some open to shared terraces. Suites are more private and many have outdoor hot tubs. There's also a stunning spa built into a natural cave formation. Next door, the much smaller Aenaon Villas lacks a restaurant or bar, but it has cheaper rates in the same gorgeous location. 

What differentiates four-pearl Rocabella Deluxe Suites & Spa Santorini from most of the other luxury properties on the island is that it has four swimming pools, a full spa, and two restaurants; most hotels in this price range have just one pool and restaurant, and spas are even more rare. However, three of the pools (including the one with an infinity edge) are narrow. Views of the Aegean Sea can be admired from beds and balconies in the spacious rooms. Rocabella is located on the picture-perfect Caldera side of the Aegean Sea, off the beaten path between Fira and Oia. Some find it isolating while others appreciate the escape from crowds. If you must be part of the scene in Oia, compare rates at Andronis Luxury Suites.

Pegasus Suites & Spa, a luxury hotel set in the caldera cliff-face in the peaceful Santorini village of Imerovigli, blends in with the Cycladic architecture of the island. While immaculate throughout, the 18 suites and villas, many designed to resemble caves (without the mustiness), are particularly outstanding -- some have private hot tubs and plunge pools, and all have exceptional views. The on-site gourmet restaurant, outdoor pool with pool bar, spa with indoor pool and hammam, and pre-ordered Champagne breakfasts delivered to private terraces contribute to an atmosphere of secluded luxury. Travelers might want to compare rates with the nearby Honeymoon Petra Villas, which has a larger pool but less-luxurious suites.

Dreams Luxury Suites is indeed a seriously upscale, suites-only property located in the relatively quiet village of Imerovigli just north of Fira. All six suites are spacious with comfy lounges, separate bedrooms, and colorful mosaic bathrooms; the highlight is that each has an outdoor heated whirlpool or plunge pool (all but one have both) with those superb caldera vistas. Room service via iPad app and Champagne breakfast delivered each morning also mean couples don't even need to leave their room. If lack of a restaurant or spa is a problem, however, check out Avaton Resort the other side of the village. 

The upscale Pantheon Villas offers a combination that's almost unheard of in Santorini: uninterrupted caldera and sunset views, privacy, and sprawling space. The chic property is built off of the pedestrian path that meanders from Fira to Oia, and doesn't see the same press of crowds or traffic you'll find in the neighboring villages. The hotel has one of the largest (and chicest) pools in Santorini. There are 20 beautiful room options; five of them are villas with private pools. All guests get free breakfast and half-board packages are available at the excellent restaurant with indoor and outdoor dining. Expect a 30-minute walk to the heart of Imerovigli, the nearest village. For those who want caldera views and to be within a quick walk of restaurants and shops in Imerovigli, check rates at Heliotopos Hotel.

Honeymoon Petra Villas is an upscale property featuring strikingly original volcanic rock architecture perched on a lofty cliff face in the quiet Santorini village of Imerovigli. As well as impressive construction, the hotel also boasts one of the largest pools on the caldera, with a 24-hour poolside bar and daybeds (both rare on the island). Rooms vary widely in size from tiny to spacious, though all open to gorgeous sea-view terraces. Lower-tier rooms and bathrooms are so small it's better to look elsewhere if on a budget, but though those wanting to splash the cash will find this an excellent upscale option. Just note that the in-room Wi-Fi is barely usable and unlike at Astra Suites, there are no rooms with plunge pools (though some have hot tubs).