The ultimate Santorini summer home escapes

Destinations

Fully immerse yourself in Greek island life in an idyllic villa on the island of Santorini, where you can swim in a cobalt-blue sea, drive around tranquil whitewashed villages to buy your morning Spanakopita (spinach and feta pastry), and sunbathe in blazing sunshine when it's safe to do so. Your only challenge is finding the best vantage point to take in this island's dreamy vistas.

Continue reading for Santorini’s highest-rated flexible vacation homes, according to global travelers.*

Ikia Kriton

Have a glass of wine with a surreal Aegean Sea backdrop at Ikia Kriton

Have a glass of wine with a surreal Aegean Sea backdrop at Ikia Kriton

This old stone house is built into the cliffs on the edge of Santorini’s caldera, a crater that was partially submerged by the Aegean Sea after a volcanic eruption about 3,600 years ago. Views out onto this half-moon-shaped bay are highly sought after, and hundreds of thousands of visitors come each year to witness the soulful sunsets over whitewashed villages, a cobalt blue-sea, and maroon cliffs. The unblemished panorama of the island from this house’s broad terrace is a valuable asset and a heavenly spot for an early morning coffee or a night cap brought to you by welcoming hosts Kriton and Eirini, a mother and son duo.

Anemi House & Villas

The infinitely-instagrammable color palette of Anemi House & Villas

The infinitely-instagrammable color palette of Anemi House & Villas

A traditional Santorini cave house painted pink, lilac, and blue, Anemi House & Villas is as photogenic as the caldera itself. It’s laid out like a rabbit warren, with gray stone stairs and private pockets of terrace punctuated by a plunge pool. Shaded by olive and palm trees beside overflowing flower pots, you’ll have a wide choice of places to enjoy a glass of wine in the evening sun. The house has everything you could ever want on vacation: An attentive but unobtrusive owner, Dimitris, beautiful monochrome suites varying from bright white to royal blue and hot pink, 360-degree views of the island from the rooftop, outdoor hot tubs, and lots of local markets.

Azalea Houses

Azalea is an 18th-century winemaker's house with peach-colored brick walls

Azalea is an 18th-century winemaker's house with peach-colored brick walls

A restored, 18th-century winemaker’s house with mud brick walls, Azalea Houses is authentically and traditionally Greek. At the same time, it’s the height of luxury with a minimalist aesthetic. The curved, peach-colored exterior creates a glorious color palette against the blue of the sea and sky. Walk to the nearby and famously pretty town of Oia, or find a private corner of the terrace while reading a book in a hammock shaded by fuchsia flowers.

Solstice Luxury Suites

Solstice Luxury Suites's rooftop pool is the perfect setting for drinks after dark

Solstice Luxury Suites's rooftop pool is the perfect setting for drinks after dark

This whitewashed, cliffside Santorini villa is a masterpiece of minimalist design and Greek island appeal. The suites are all smooth lines and white linen, and the terrace has views of nothing but deep blue sea from the box-like rooftop swimming pool. Be sure to enjoy a drink here after dark, when it’s lit up with cacti planted around it like abstract sculptures. Additional perks include private hot tubs and a wonderfully hospitable staff led by Hercules and Nikos.

Cleo's Dream Villa

Cleo's Dream Villa is situated just below Santorini's famous blue-domed church

Cleo's Dream Villa is situated just below Santorini's famous blue-domed church

Beneath this cliffside villa, greenery flourishes in the fertile, volcanic soil and leads down to the sea, while above it you can see Santorini’s famous blue-domed church, the Three Bells of Fira. Its location is right in middle of the beautiful town of Oía, though it’s so quiet you wouldn’t know it. It’s also close to the beach, so you’ll be able to choose whether to relax in a private hot tub, rooftop pool, or a white sandy cove. The rooms themselves are decorated in soothing beige, gray, and rose pink, and open up to the terrace with deck chairs and a sweeping view of the caldera.

*The data scientists at Booking.com used internal data to uncover the most highly-reviewed vacation homes in Greece (they were all in Santorini).

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