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.

This 10-room boutique property rests cliffside and mid-caldera, just outside Imerovigli. Because public space is limited to the narrow, windowless lobby and the smallish infinity pool area, the vibe here is private and thus it's a romantic spot for couples. While the property is within a 15-minute walk to the center of town, there’s a hefty amount stairs to deal with. For those with mobility issues, the stair-free Anastasis Apartments (which also has a spa) may be a better bet for a slightly higher price. However, those seeking out a private holiday surrounded by beautiful views and a highly traditional aesthetic will find Artemis Villas hard to beat.

The 13-room Absolute Bliss Imerovigli Suites, an upscale, well-maintained property with personal service and competitive prices. Charming rooms and suites have indoor or outdoor hot tubs with sea views, and there's an exclusive villa with a heated pool and an indoor steam room with chromotherapy. The hotel’s outdoor pool and dining terrace ---where romantic dinners can be arranged -- offer gorgeous views. However, there’s no full-service restaurant or spa. For a property with more facilities, consider the Rocabella Deluxe Suites & Spa Santorini.

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. 

Remezzo Villas is a 12-room mid-range boutique property set among a host of hotels along the Imerovigli caldera cliffs. Displaying traditional architecture, the hotel is a suitable choice for anyone looking for a self-catered holiday without too many frills -- but with gorgeous views and sexy spaces. Due to its traditional design, many if not most of the hotel's features and spaces are small, including the pool, sun deck, lobby, and lobby bar. Guests not wanting to deal with the high amount of steps here may want to check out the nearby and similarly-priced Anastasis Apartments, which also offers a light snack service and free breakfast with slightly higher quality rooms. Rooms here, however, have a sleek island vibe.

The Altana Traditional Houses is an upscale boutique property perched high above Santorini with spectacular caldera views. This restored 1779 captain's house is built into the cliffside, and features sundecks throughout and a small pool. The 10 rooms have whitewashed walls and private terraces overlooking the Aegean, and some have jetted tubs. The Altana's organic farm provides produce for its cafe, serving traditional dishes along with cocktails and local wine. Breakfast is included (and served until late), featuring homemade Greek items. The vibe at the hotel is relaxed and romantic, with no TVs on the premises, and a quiet location in Imerovigli between Fira and Oia. Guests seeking a more active, resort-style vacation may prefer the nearby Rocabella Deluxe Suites & Spa, with its two restaurants, four pools, and gym.

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.