Santorini villas usually sell the sunset, but the island’s wine country is somewhere else: inland, in the hill villages of Pyrgos and Megalochori, where the vines grow in low baskets on volcanic ash and most of the cellars are a short drive away. These six villas and villa resorts put you among those vineyards, each with its own pool, plus one caldera estate in Oia for travelers who want the view first.
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In this article
How we chose these Santorini villas
Three rules cut the field. Every stay is bookable on Expedia, so you can check your dates through the links below. Every one gives you a private pool or shares a pool among only a handful of units, because privacy is the point of renting a villa rather than a hotel room. And five of the six sit in Pyrgos or Megalochori, the two villages closest to the island’s best-known cellars; the sixth is the exception for a first trip, in Oia.
Ratings are Expedia guest scores with the number of reviews behind them. Where a villa has only a handful of reviews, we say so: a perfect score from nine guests is a promising sign, not a verdict. The list is unordered. For the wineries themselves, start with our guide to Santorini wineries.
Pyrgos, the hilltop wine village
Pyrgos is the highest village on Santorini, a tangle of lanes below the old castle and the slopes of Profitis Ilias. It looks over both coasts, and the vineyards run right up to its edge. Santo Wines, the island’s big cooperative winery, sits on the road just outside the village.
1. Santorini Sky, Luxury Resort — Pyrgos
Santorini Sky is the most complete villa resort in the wine villages, and the one we would book first. It sits on the mountain above Pyrgos, and the villa terraces look out over the island to the sea, with the sunsets that guests single out again and again. Each villa is a self-contained retreat, and reviewers mostly mention two other things: the silence and the staff.
It suits a couple who want hotel service with villa privacy, and who plan to stay put in the evenings. The limit is the setting itself: this is a mountain retreat, not a village stay, and you will want a car or a driver for dinner out. For wine, it is right in the middle of the cellar villages.
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2. Ananda Retreat — Pyrgos
Ananda Retreat is the quiet, self-catering answer to Santorini Sky: a pair of villas on the hillside between Pyrgos and Megalochori, with a garden, a terrace and a view over the water. There is no restaurant and no lobby, which is exactly why it is here. You live like a guest in a private house and set your own hours.
Pick it if you would rather shop in the village than order room service, and if you like the idea of cooking a simple dinner around a bottle bought that afternoon at a cellar door. The limit is the review count, still small, and the lack of on-site dining: a car makes the evenings much easier.
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Megalochori, in the middle of the vineyards
Megalochori is the wine village proper: old mansions, bell towers and vineyards on every side. Gavalas Winery, one of the island’s family estates, is in the village, and the clifftop cellar of Venetsanos Winery is just down the road above the port of Athinios.
3. Soil of Sun Luxury Villas — Megalochori
Soil of Sun is the only stay on this list where the vineyard is part of the property, and that alone earns it a place. It is a tiny compound of suites and a villa at the edge of Megalochori, with the vines around it and the caldera a few minutes away on foot. The estate also runs its own tastings, so the first glass of the trip can be poured outside your door.
It is for travelers who want to wake up in the vineyards rather than drive to them. The honest caveat is size and track record: with only three units it books out fast, and the perfect score comes from very few guests so far. Treat it as a find, not a sure thing.
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Book it
Villas are booked one at a time
A villa is a single unit, not one room among many: when it is taken for your week, it is gone. If your dates are fixed, compare every villa on the island for the same nights before you commit to one village.
4. Mansion Kyani — Megalochori
Mansion Kyani is the pick for a group of friends or two couples traveling together. It is a restored village house on a rise above Megalochori, with a cobbled courtyard laid in the old island style, three separate bedrooms and a pool deck built of volcanic stone that looks across the vineyards to the sea. It feels lived in, not designed for a brochure.
You rent the whole house, so the price only makes sense if you fill it. In return you get the most generous space on this list and the longest review record of the private houses here. The listing also offers a small manual rental car at no charge on standard rates, which settles the question of how to reach the cellars; check that it applies to your booking.
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5. Volcano Flame — Megalochori
Volcano Flame is the caldera view without leaving wine country. The village is only a few minutes’ walk from the caldera rim, and from this small villa the pool looks straight across the water to the volcano islands. It is the most romantic stay among the vineyards, and the closest a Megalochori stay gets to an Oia sunset.
It suits a couple who want the view and the vines in the same place. The limits are a small review record and no dining of any kind on site: you eat in the village or at the cellars. Venetsanos is close enough that a sunset tasting there and a short drive home is an easy evening.
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Oia, if the view comes first
Oia is the far northern tip, the village on every postcard, and it is a long way from the southern vineyards. A villa here makes sense if the sunset is non-negotiable and the wineries are a day out. For more hotels across the island, see where to stay in Santorini for wine lovers.
6. Canaves Epitome — Oia
Canaves Epitome is the full-service option for travelers who want a villa and a resort at once. Built in dark stone a short walk from the castle, it keeps a little distance from the lanes that fill with day-trippers at sundown. The villas are the reason to come: a private pool, your own terrace, and staff a phone call away.
It is the splurge here, and the farthest from the cellars of Pyrgos and Megalochori, at the other end of the island. Plan one wine day with a driver, perhaps on a Santorini wine tour, and keep the evenings for Oia.
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When to book a Santorini villa
Late spring and early fall are the sweet spot for a wine trip: warm enough for the pool, cooler than August for walking between cellars, and the tasting rooms are all open. The harvest on Santorini starts early, usually from mid-August, when the white grapes come in first and the island is at its busiest.
Villas are single units, so they sell out faster than hotel rooms for the same week. For May, June, September and October, booking several months ahead is sensible, especially for the small properties in Megalochori. Some of the pools are seasonal, open roughly from April to October, so a winter stay is quieter but not a swimming holiday.
Getting there and getting around
Santorini’s airport is on the east side of the island, a short drive from Pyrgos and Megalochori, and the ferries arrive below Megalochori at Athinios. From the wine villages, everything else is a drive: Fira is close, Oia is across the island. Buses link the main villages, but a car or a driver gives you the cellars on your own schedule. Our guide to renting a car for a wine trip in Europe covers insurance, documents and drink-driving rules.
Compare car rental in Santorini →
If you plan to taste seriously, book a driver for that day, or pick a villa within walking distance of a cellar: Santorini Sky, Soil of Sun and Mansion Kyani all are.
Choosing between them
For a couple who want service and the best address in wine country, Santorini Sky. For privacy and a kitchen on a smaller budget, Ananda Retreat. For sleeping in a working vineyard, Soil of Sun. For a group, Mansion Kyani. For the caldera view from wine country, Volcano Flame. And if Oia is the dream and the wineries are a day trip, Canaves Epitome.
Whichever you pick, give the cellars a proper day: Santo Wines for the view and a wide flight, a family estate in Megalochori for the stories, and Venetsanos at sunset. Our guide to visiting Santo Wines explains how to book it.
Prices are “from” rates, indicative and set by our booking partners: they change with dates and availability, so check the current rate on Expedia.
