Beautiful as it undoubtedly is, Santorini is the product of an ancient catastrophe. Around 1600BC, the volcano at the centre of the island exploded in a massive eruption before collapsing in on itself, leaving behind just a rocky fragment of its rim, or caldera — the slender semi-circle of rock we now know as Santorini. The Greek island remains volcanically active: there have been several eruptions since, most recently in 1950 on the neighbouring island of Nea Kameni.
Santorini’s volcanic origins explain why there’s precious little white sand to speak of. Here the beaches are nearly all black, ochre or red, and there are more pebbles than on other Cycladic or Ionian islands. However, what the island lacks in soft white sand, it more than makes up for in views. Santorini has one of the Mediterranean’s most memorable sunsets, best seen from the west coast, where the rocky cliffs plunge vertiginously into the brilliant blue sea.
The capital is Fira, a busy, attractive town on the west coast. Ten miles north is Oia: the island’s most photogenic village, known for its white sugar-cube houses at the top of the cliffs. On the southern side of the lagoon is Akrotiri, home to an archaeological site where an ancient Minoan city was discovered in 1967; it’s still in the process of being excavated, and has an excellent archaeological museum. But wherever you fancy staying in Santorini, we’ve got the perfect villa for you.
Main photo: Villa Nautilus, Firostefani (Expedia)
1. Caldera Premium Villas, near Oia
Best for cave living reinvented
No modernist box, this. Instead you will find a modern reinvention of a cave house, a style of architecture on Santorini that’s been around for centuries, naturally designed to ward off the punishing summer heat. Stark white walls, domed ceilings, rough walls and alcoves make it feel traditionally Greek, while minimalist furniture and glazed windows feel decidedly contemporary. Outside, on the small terrace, there’s a shady plunge pool and stunning vista over Oia’s cliffs.
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Pool Y
Family-friendly N
Sleeps 2
Price £££
2. Aspro Spiti, Oia
Best for caldera views
This higgledy-piggledy villa sits at the top of Oia in the Perivolas neighbourhood, and feels like a Grecian hobbit house, with whitewashed spaces seemingly hollowed out from the rock, patches of exposed stone and little staircases connecting the various rooms. It’s broadly on three levels: a ground-floor bedroom, a middle-level lounge-diner with a kitchen and second bedroom, and a third-level “loft” suite with a private balcony and roof lights on to the sky. A romantic arcaded plunge pool and cute gated garden — with a sea view, of course — complete the package.
Pool Y
Family-friendly Y
Sleeps 6-8
Price ££
3. Home of Lilies, near Firostefani
Best for bags of space
There’s space to spare at this sprawling villa, in an inland, out-of-the-way location about halfway between the main town of Fira on the west coast and Yalos on the east — you’ll definitely need a car to get here. It has a huge lounge, a well-equipped kitchen and four rooms that will easily sleep eight people; and while the decor isn’t as fancy as some of the island’s top-end properties, it’s pleasant enough. Brownie point: the outdoor pool is generously sized.
Pool Y
Family-friendly Y
Sleeps 8
Price ££
4. Villa Sophia, Megalochori
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Best for peace and quiet
Tranquillity is what you snare this charming village house for. It’s in the pretty, quiet hamlet of Megalochori, near the main square, and has the feel of a real, lived-in Greek house, with solid wooden furniture, dark panelled doors, wrought-iron beds and sepia-tinted photos — though it’s the delightful courtyard garden, framed by bougainvillea, palms and olive trees, where you’ll probably spend most of your time. There are hammocks to lounge on, a private pool and a view of the village church tower. It’s all rather dreamy.
Pool Y
Family-friendly Y
Sleeps 4
Price £
5. Athiri Villa, near Finikia
Best for value
Athiri is a sweet — and sensibly priced — little villa, typical of the island’s Cycladic architecture, with sugar-white walls and pale blue shutters. It’s in a small complex of three similar villas known as the Vino Houses, but feels very private, with a patio overlooking vineyards and a stripe of blue sea on the horizon. Two bedrooms mean it’ll sleep four — the only drawbacks are the detached bathroom (a bit of a pain in the middle of the night) and the lack of a proper pool, although the shaded plunge pool is perfectly adequate for cooling off. A complimentary breakfast prepared for you daily and bath goodies from Yves Rocher add extra spoil-factor. The villas lie on a backroad north of Oia, near the quiet village of Finikia; Baxedes beach is about 15 minutes away on foot.
Pool Y
Family-friendly Y
Sleeps 4
Price £
6. Villa Alpha, Imerovigli
Best for couples
Acrophobes beware: this gravity-defying villa teeters above a drop so vertiginous it feels as though you’re floating on air. Though small, this is a lovely hideaway for couples, with a level of luxury detailing that would put most boutique hotels to shame: sleek stone sinks, a walk-in shower, a romantic bedroom with a black marble tub, a cliffside patio and an angular outdoor pool that, from certain angles, seems to meld into the Aegean. It’s in Imerovigli, a small village north of Fira.
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Pool Y
Family-friendly N
Sleeps 2
Price ££
7. Windmill Villa, near Pori
Best for a taste of windmill life
Here’s something different: a converted windmill that still has its original sails. It’s situated on the island’s northeast coast — the sunrise side — and while this pad lacks the classic caldera views, it makes up for it in character. A spiral staircase winds up through the mill to two circular bedrooms, both en suite and decorated in soft pastels and floral fabrics, while little square windows peep out along the coast to the sea. The pool and terrace is shared with other mill villas. The quiet, sandy cove of Pori Beach lies just to the north.
Pool Y
Family-friendly Y
Sleeps 4
Price ££
8. The Villa at Grace, Imerovigli
Best for an exclusive feel
Few Santorini villas can match the style and sophistication of the Grace, the island’s premier boutique hotel. Perched above a rocky promontory, it offers just one, super-luxurious villa that spares no expense nor spoil: two deluxe bedrooms, a private spa and hammam steam room, an on-call chef to make your meals, a wine and cigar bar, a panoramic pool — plus all the added benefits of the island’s top hotel, including a yacht, yoga school, concierge service and fine-dining restaurant run by stellar chef Lefteris Lazarou.
Pool Y
Family-friendly Y
Sleeps 4
Price £££
9. Oia Mansion
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Best for period grandeur
This grand, neoclassical mansion is an Oia landmark, constructed around 1870 for a wealthy shipowner, and is still owned by his descendants, the well-to-do Nomicos family. With its imposing coral-pink façade, period rooms and sumptuous antiques — from Venetian mirrors to ornate chandeliers and armoires — the house offers the kind of period grandeur that’s hard to find these days. Despite the house’s size, the four bedrooms are all surprisingly compact, with traditional Cycladic white walls to keep out the heat. The pick is the Sea Captain’s bedroom on the ground floor (you can also visit the captain’s old office, which still contains his books and typewriter). Outside there’s a patio framed by wrought-iron fencing, and another terrace with a Jacuzzi and sundeck; there’s also an interior courtyard that’s perfect for a shady lunch. Breakfast is provided, and a chef is on hand to prepare meals should you so wish.
Pool Y
Family-friendly Y
Sleeps 8
Price £££
10. Aria Villas, Fira
Best for modern style
Four villas, all named after operas, are available at this smart hotel in Fira. They’re different in layout, but all the villas offer the same sleek, modern aesthetic (brushed concrete floors, open-plan spaces, Smeg fridges). Fidelio has a romantic staircase leading up to a mezzanine bedroom; La Traviata has a cave-like plunge pool; and the best view is from La Vida Breve, which has direct access to the rooftop Jacuzzi (rather oddly, it’s private apart from three hours every evening, when it’s shared with other guests). Guests have access to all the hotel’s facilities — including the pool — and the location in bustling Fira means there are lots of shops, restaurants and bars nearby.
Pool Y
Family-friendly Y
Sleeps 6
Price £££
11. Nafsika Estate, near Megalochori
Best for the celebrity lifestyle
Need your own helicopter pad? Simply can’t get by without your own butler or personal chef? For movie-star, money’s-no-object luxury, this sprawling house is perhaps the most ostentatious of all the villas in Santorini. In an isolated spot cut into the cliffs near Megalochori, surrounded by swathes of uncompromising concrete, it looks for all the world like a Bond villain’s lair. It’s vast, too: five bedrooms, a domed living room, a massive dining room that seats ten, and an eye-popping terrace fronted by glass that looks directly out into the caldera. The finish is impeccable, of course — but it all comes at quite a price.
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Pool Y
Family-friendly Y
Sleeps 10-12
Price £££
12. Virginia’s Cave Villas, Oia
Best for cave-house chic
Flintstones-chic in ever-popular Oia — these cave houses offer something refreshingly different to the sleek lines and sharp edges of many of Santorini’s villas. Burrowed into the cliff face, they’re a hipster’s take on a monastic cell: archways, rounded ceilings and smooth stone surfaces, married with natural fabrics, cane furniture and funky, grotto-like bathrooms. All the villas have gravity-defying cliffside patios where you can soak in the hot tub with a majestic Mediterranean view — but it’s definitely worth bumping up to Grand or Superior for maximum space.
Pool N
Family-friendly N
Sleeps 2
Price £
13. Aenaon Villas, near Imerovigli
Best for getting close to the caldera
Head into the clouds (if there ever are such things on Santorini), on one of the highest points of the island; a remote spot, ten minutes’ drive north of Imerovigli, roughly halfway between Oia and Fira. You’ll find this adult-only villa along with a cluster of others on a rocky red hilltop, high on the rim of the caldera. They’re typically Cycladic in design, ice white, with domes and chimneys, little brick fireplaces, shuttered windows and private verandas that lead out on to a communal terrace and infinity pool. Heaven in villa form.
Pool Y
Family-friendly N
Sleeps 2
Price £££
14. Anemi Villa, Oia
Best for a splash of colour
This unusual house offers a change to the usual Oia sugar cubes: bright pink, and originally a sea captain’s residence, it zings with colour and fun. Close to the heart of Oia village, it’s light and airy inside, with oak floors, high ceilings and marbled stone surfaces. There are three bedrooms, all with their own bathrooms (in grey, brilliant blue and punk pink); stairs ascend to a small roof courtyard with a plunge pool and, at the top of the house, a grandstand view across the village’s rooftops to the caldera. Several cute cave houses are also available.
Pool Y
Family-friendly Y
Sleeps 6-8
Price ££
15. Villa Nautilus, Firostefani
Best for tradition
Lost amongst the warren of white houses in Firostefani, this tucked-away house provides a classically Cycladic stay. It’s traditional in feel — domed ceilings, plaster walls, terracotta-tiled floors, shutters — but it also has an intriguing history, with memorabilia left over from the days when it belonged to a merchant seaman. There are three bedrooms: two in the main house, and a romantic master in a separate building across the cobbled courtyard. Stone steps lead up onto the rooftop terrace and an absolute knockout of a plunge pool.
Pool Y
Family-friendly Y
Sleeps 6
Price £££
16. EroSantorini Estate
Best for next-level luxury
This is the one for the ultimate family-and-friends escape: your very own private island estate, in an ultra-secluded spot about a mile south of Fira. Each suite provides glorious privacy, with lovely shared spaces providing ample room for alfresco get-togethers. There’s a communal terrace and alfresco kitchen for lazy lunches, a cliffside fire pit for late-night barbecues and of course a private chapel, outdoor cinema and poolside “serenity cave” to relax in. The setting is incredible too, set amongst citrus trees and fragrant shrubs, with a working kitchen garden to pick a few Mediterranean herbs for supper. This really is next-level luxury — infinity pools are ten-a-penny on the island, but infinity pools with their own underwater sound system?
Pool Y
Family-friendly Y
Sleeps 10
Price £££
17. Villa Kassie, near Pyrgos
Best for a place in the country
Book this pad for something different to the usual Santorini style. Instead of being on the caldera’s edge, here you’re inland near the fortress village of Pyrgos, with a widescreen panorama across fields and plains to the coast and the distant island of Tholos. Built from rustic stone, this pad looks rather like a hilltop castle. The bedrooms are cosy: curvy walls, nooks and Grecian fabrics give character, while the cave-style kitchen has a glass roof and a funky, bright orange Smeg fridge. Outside there’s a spacious wooden deck complete with a pool; the sunset view is magic.
Pool Y
Family-friendly Y
Sleeps 6
Price £££
akvillas.com
18. Presidential Villa, Akrotiri
Best for a multi-family break
Gloriously detached, in a prime spot on the southern edge of the caldera, this grand villa feels more palatial than presidential. With seven bedrooms, it’s a brilliant option for a multi-family holiday. Composed of stacks of white boxes, like an oversized Lego experiment, it’s extremely spacious, with rustic arches, shuttered windows and those smooth white walls that are characteristic of Santorini. As so often, the outside space steals the show, especially the Aegean-facing panoramic pool — and there’s a boutique hotel nearby where you can use the spa, gym and restaurant. Many of the island’s best-known beaches are within easy driving distance, including Red Beach and White Beach.
Pool Y
Family-friendly Y
Sleeps 14
Price £££
bluevillascollection.com
19. Villa Tatusa, Oia
Best for catching the sun
There’s not just one sunbathing deck at this luxury villa in Oia, but two — along with a knockout pool overlooking red cliffs and blue waters. Like much of Santorini’s architecture, from the outside, the house looks like it’s been fashioned from cake icing: all swooping forms, curves and archways fashioned from brilliant-white plaster. Inside, brushed concrete gleams in the kitchen and bathrooms (the rustic rock sinks are a nice touch), and the villa’s layout means there’s flexibility to book one, two or three bedrooms. The steep terraces, steps and hard stone surfaces mean it’s probably not ideal for small children.
Pool Y
Family-friendly N (better for older children)
Sleeps 6
Price ££
akvillas.com
20. Villa Mystiko, near Firostefani
Best for location
A knockout cliffside position is the main selling point at this uber-stylish villa, built on the rockface above Firostefani — the highest part of the island’s capital, Fira, famous for its magnificent sunset view over the caldera. The villa is laid out in open-plan fashion, with vistas unfurling through every window, including from both bedrooms, one of which has its own corner hot tub. The design details are well thought out — a marble coffee table, oversized light bulbs, minimalist black lampshades — but all eyes are drawn here to the cliffside terrace, where there’s the obligatory infinity pool and a patio that seems to hover above the Aegean.
Pool Y
Family-friendly Y
Sleeps 4
Price £££
akvillas.com
21. Villa Kamari, Kamari
Best for families
This handsome arcaded villa is a long way from the crowds, on the quiet southeast side of the island, in the shadow of Mount Vouno. It’s a perfect Santorini retreat for families: four smart, unfussy bedrooms sleep up to eight, and there’s a spacious, pine-shaded terrace with a seriously impressive (and very private) pool. Better still, you’re just steps away from the black volcanic sands of Kamari Beach and its seafront restaurants and bars — and the location is perfect for sunrise.
Pool Y
Family-friendly Y
Sleeps 6-8
Price £££
akvillas.com
22. Chromata San Nicholas Cave House, Imerovigli
Best for hotel amenities
This dizzyingly positioned villa has the best of both worlds: a sleek, cave-like pamper pad, with the added benefit of being on the grounds of one of the island’s top hotels, Katikies Chromata (with amenities including infinity pool, spa and a brace of restaurants). It’s in Imerovigli, a slightly less hectic caldera-view village than Oia. The villa is spread over a couple of levels, with the usual luminous white plaster walls and passageways you’d expect from a Santorini cave house: there’s a grotto-like master suite and a second bedroom with steps onto the patio, where there’s a small plunge pool for a dip.
Pool Y
Family-friendly Y
Sleeps 5
Price ££
ihg.com
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