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.

While the Hotel Sunny Villas is a perfectly decent take on the traditional island-style property, it's really all about the views. It is set in the charming and fairly quiet Imerovigli village just north of Fira with a mixture of cave-style and more modern accommodation -- all clean and nicely presented. Although all rooms have their own terrace, some are separated by a walkway. Though there's a small pool with deck chairs, there is no restaurant or spa (not unusual for this price range). The sunsets, however, are no less stunning than at other cliff-top hotels in the area and rates are relatively good value. It's worth comparing prices with the more upscale (but sometimes not more expensive) Afroessa Hotel, however.

Prekas Apartment is one of the best values on the caldera in Imerovigli. Nine cave-style rooms with Aegean Sea and Skaros Rock views cost a fraction of what they do in neighboring villages of Fira (about a 20-minute walk) and Oia (about a 20-minute drive). Imerovigli Village itself is one of the quieter caldera villages, but it has a handful of souvenir shops and Greek restaurants. Though the rooms are spotless and come with kitchens or kitchenettes, they could use a style infusion, or at least some new bedding. Perks include a small outdoor plunge pool, continental breakfast delivered to rooms (for a fee), and a helpful front desk staff. Note that there are lots of stairs to navigate to reach the front desk, pool, and some rooms. As an alternative, the Heliotopos Hotel is more chic and includes a hot and cold breakfast buffet in the rates. 

Krokos Villas is a 16-room, mid-range property comprising three different parts set among the rambling assortment of properties in the center of Imerovigli village. Rooms can vary a lot, largely dependent on whether or not they've been renovated yet, though all have basic kitchenettes and open to sea-view terraces. While breakfast can be delivered to your room, there's no real restaurant and the lack of a proper pool or spa is also a letdown. Rates, however, do tend to reflect the hotel's shortcomings and are some of the cheaper you'll find in this pricey market. If there's a bit of room in the budget, compare rates with the The Rocabella Deluxe Suites & Spa, which has more features and is sometimes only slightly costlier.