Tramountana, Vourvoulos

Life at Tramountana is laid back and luxurious. The villa is uncluttered and simple, helping you forget all the stresses and worries you left back home. You’ll have no trouble settling in here, especially when you find out about the garden that borders the villa filled with herbs and seasonal vegetables. You’re welcome to help yourself to both. The villa is set in Vourvoulos, a hillside village in the center of the island. In the late afternoon, the romantic outdoor dining space encourages you to serve up a freshly barbecued feast and enjoy the day’s final moments of sunshine. It all leads up to a glorious finale; if you’ve ever been to Santorini, you know the sunset is the main event. If not, you’re about to find out at Tramountana.

Blue Angel Villa, Fira

Blue Angel Villa is a traditional cave house (known on the island as a canava) turned luxurious vacation retreat. Originally built in the 17th century, the home stays true to its historical roots in the form of handmade floor tiles (imported from Italy) and traditional stonework. Now, it’s a picture of modern Santorini with all the technological amenities today’s travelers expect: 3D TV (with glasses), Blu-Ray player, an iPod dock, and a computer with Wi-Fi access. When you arrive you enter through an intimate courtyard high up on the clifftop, to find the welcoming interior and outdoor space complete with hot tub. After a short 10-kilometer transfer from the airport into Fira, you’ll be treated immediately to a complimentary bottle of local wine and a basket of local goodies. The biggest treat of all, of course, will be your view of the caldera on Santorini’s western tip at the end of the day.

Villa Estelle, Imerovigli

Welcome to this cozy, curvy home on a hillside in Imerovigli, far away from the tourist crowds and perfect for families and small groups. Villa Estelle is clean and compact with a snow-white exterior that gives it a classic Greek look and feel. Inside it’s as comfortable as your own home, and equipped with Wi-Fi so you can stay connected as well as a juicer and coffee maker for the perfect start to your mornings. Outside, you’re spoiled for choice: from the heated plunge pool to the rooftop garden (ideal for an early morning yoga session) to the poolside dining and the sun terrace connected to the living room, there’s no shortage of options from which to watch those lavender sunsets.

Mansion Kyani, Megalochori

Megalochori is a quiet, traditional Greek village along the west coast of the island, known for its vineyards and wine tastings. High atop a hill in the heart of Santorini, you won’t have to go far to feel surrounded by Greek culture. Learn the language, interact with friendly locals, take a cooking lesson, or participate in a Greek singalong – you’ll feel like you belong in no time. Mansion Kyani is embedded in the culture. With the Aegean Sea in the distance and two luxurious living areas, Kyani is one of the best bang-for-your-buck villas you’ll find in Santorini. The Holy Mary Church takes over the skyline, and in the evening, you’ll want to grab a spot on the couch by the pool, surrounded by loved ones, and take it all in.

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