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Santorini is one of the world's most recognisable and photographed destinations — the white-washed buildings and blue domes of Oia against the volcanic caldera is an image burned into global consciousness. A VRBO villa in Santorini is genuinely one of the great travel experiences. Here's how to do it right in 2026.
The Best Villages for a VRBO in Santorini
- Oia: The most famous — and most expensive. Sunset views are world-renowned. Book 6–12 months ahead for peak season. Worth every penny.
- Fira: The capital — more accessible, good transport links, restaurants and nightlife. Less exclusive than Oia but more practical.
- Imerovigli: Between Fira and Oia — often called the best caldera views on the island. Quieter than both with outstanding VRBO options.
- Pyrgos: The highest village — panoramic views, medieval castle, less visited. Excellent for those wanting the real Greece alongside the Santorini spectacle.
Cave Houses — The Unique Santorini Experience
Santorini's traditional architecture includes cave houses (skafta) — properties carved directly into the volcanic rock. Cool in summer, atmospheric year-round, unique to the Cycladic islands. Many of the best VRBO listings in Oia and Imerovigli are cave houses, often with private plunge pools cut into the cliff edge with caldera views.
Santorini Practicalities
- Fly into Santorini airport (JTR) — flights from most UK airports in summer season
- Island is small — car hire useful but ATVs and taxis also work
- Peak July/August is intensely crowded in Oia — May, June and September are better
- The caldera sunset is real — genuinely one of the world's great natural spectacles
- Wine: Santorini Assyrtiko white wine is extraordinary — try Domaine Sigalas
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Caldera-view villas, cave houses and luxury retreats across Santorini. Filter by caldera view, pool and village.
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Sento earns a referral if you click through our links — this never affects our recommendations. Prices and details correct at time of publication. Updated April 2026.