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Sea cliffs covered in whitewashed houses. Panoramic views of the sparkling Aegean Sea. Endless sunshine. Artfully terraced towns. These are just some of the reasons the island of Santorini is one of the most popular tourist destinations in Greece.
Located 200 km (120 mi) southeast off the coast of the mainland, Santorini forms part of the historic Cyclades islands, with its circular archipelago and sunken crater revealing its volcanic past. The tall cliffs offer some of the best sea views anywhere, but it’s arguably the island’s unique architecture that draws the most attention.
Most of the houses on Santorini take after the traditional Cycladic style, meaning the primary colors are the white and blue of the Greek flag. The most iconic are in cities like Fira: multi-storied homes with blue doors and window frames. There are other styles of buildings as well, such as the yposkafo cave houses, which are carved into the facades of volcanic rock walls.
With such simplistic beauty, the Cycladic architecture takes one’s breath away, and there’s no better way to truly appreciate it than by enveloping yourself in all its whitewashed, undulating glory.
Tastefully styled, outfitted for the modern traveler, and framed by jaw-dropping island views, these are the best villas for rent in Santorini for a 2020 getaway beyond compare:
Dana Villas, Santorini
To experience the historic cliff house style but with a modern touch, the Dana Villas in Firostefani offers the perfect mix. The airy rooms, which are tastefully outfitted with light grey and robin’s egg blue furniture and decor, extend back into the cliffside, with cavernous spaces housing pools, bathrooms, and bedrooms.
But where the Dana Villas really stands out are the views; each room opens onto a sweeping panorama of the oceanic caldera, while the more upscale villas (such as the Honeymoon and Infinity Villas and Suites) include outdoor terraces, infinity pools, and Jacuzzis.
The Hector Cave House
The Hector Cave House (which is considered one of the finest AirBnbs in Santorini) is a rendition of another Santorini classic: the canava wine cellar. Carved into the caldera walls more than 250 years ago, this was originally used as a summer house by a local family before being converted into an upscale rental.
Measuring 60 m2, the white cave house comes with a loft bedroom, two bathrooms, a living area, and kitchen, but the crown jewel is the ocean-view terrace, complete with seating area and a cold plunge pool.
Native Eco Villa
True to its name, this luxury villa – located on the caldera rim – not only offers a truly cushy retreat experience, but you can feel good about doing it: the property is eco-friendly.
Part of a grouping of three high-end villas and built in the cliff home style, the Native Eco Villa stands out from its sisters with its understated decor and warm accent colors, such as the use of wood furniture and a charcoal-colored veranda floor. It can accommodate up to 8 people in its four bedrooms, is equipped with a kitchen and living area, and has a rooftop veranda and Jacuzzi.
The Small Architect’s House
Poised on the highest point on the island in the village of Pyrgos, the Small Architect’s House channels the usual vibe of Santorini houses, with its white walls, open flow, and gentle corners, but it has a twist. Designed by Oikos Architecture, the house has been given a more contemporary feel by foregoing the traditional blue doors and windows for dark wood accents and an adobe-brown courtyard floor, infusing the space with a more earthy feel.
Inside, brightly colored furniture (like a hot pink dining set and a yellow chandelier) add a touch of whimsy to the classic rounded white rooms. The two stories each come with their own bedroom with ensuite bathroom, complemented by a kitchen, vaulted and airy dining/living area, and walled outdoor veranda.
Sophia Oia Villa
At the sophisticatedly simple Sophia Oia Villa, purity is truly the name of the game. There are no fancy design gimmicks: just a villa that understands that a little goes a long way.
Located in the village of Oia, its multitude of curving or straight-edged rooms give the impression of being in a stylish Dr. Seuss house. Carefully placed decor elements like a wooden ladder transform the rooms, with teal blue doors and windows opening onto the ocean and village vista. Inclusive with a stay are services like housekeeping, and day trips can be organized around the island.
There is nothing like a night at the opera, or in this case, the Opera Mansion. This classy hotel was converted from a historic opera building into a single private suite, making it an ideal honeymoon destination.
Guests enter via a domed archway and descend the staircase to the private courtyard with pool, Jacuzzi, and ocean-view terrace. Inside, large arched rooms provide the perfect escape for the suite’s two guests, with a heated turquoise pool, personal steam room, and wine cellar accompanying the spacious bedroom.
Modern, minimalistic, and oh-so chic: that’s Villa Ariadne. Run by luxury outfit Cloud9, this one-bedroom suite villa is decorated with all kinds of trendy design flourishes, like contemporary free-floating stairs and funky light fixtures.
On top of all this, the property also comes with all necessary modern amenities, including a truly decadent bathroom (and indoor pool with massage jets). A rooftop veranda with a heated pool, Jacuzzi, and 360-degree views of the Adriatic Sea and the other islands of the archipelago is the cherry on top.
This stately villa, renovated from its first life as a wine and tsipouro (Greek brandy) factory, is considered one of the most refined Santorini rentals.
The island’s sculpted houses are famous for their gentle curves and corners, but Villa Fabrica has decided to take a more contemporary approach and is all about the sharp lines and angles, creating a crisp look. Split into four units, it pampers guests with amenities such as terrace pools, breezy living rooms that open up to the fresh air, and Jacuzzis.
Gitsa Cliff Luxury Villa
Built in the style of the yposkafo cliff houses, the Gitsa Cliff Luxury Villa ups the ante with its Art Deco-esque furnishings and accent colors. Guests enter onto a chic veranda with tiled floor and bubbling Jacuzzi, followed by the living room, with its plush couch and chairs, front room table, and coffee/wine bar. Further back into the cliff can be found the cavernous bedroom and bathroom. Soft, recessed lighting completes the vibe.
As Gitsa is a cliff house, there’s only one level, with the rooms branching off each other back into the cliff face, but above the entrance veranda, there is a small rooftop sunning area with sun chairs where one can relax and drink in the oceanic views.
Kamini Santorini Villa
The sea views from almost anywhere on the island are incredible, but the vista from the large private deck of the Kamini Santorini Villa is one of the best: rolling hills covered with white houses stretching down to the sea. And all this you can enjoy from the comfort of your infinity pool and back deck – complete with dining and barbecue area.
Stylistically, this opulent villa also stands out from the rest with its choice of exposed stone exterior walls, evoking a more rustic vibe. Inside, the classic white rooms seamlessly flow together to connect the full kitchen, bedroom, bathroom, and living area. Splashes of orange in the decor offer just the right amount of variation.
Classically Mediterranean with its white walls and stone accents, this gem of the Aegean started life as an 18th-century canava wine facility. First impressions matter and Villa Cyrene knows it: you immediately enter into a lovely courtyard with a cobblestone floor, blooming flowers, warm walls, and staircase to the second floor with its outdoor hot tub.
Retreat inside to escape the Santorini sun, where the airy rooms, initially designed to keep the wine cool, offer hours of relaxation, whether cooking a romantic meal in the fully equipped kitchen or reading a book in the living area. Then step out and explore the surrounding village of Megalochori or take the included rental car to discover the rest of the island.
As the name suggests, the first thing that draws the eye on the Windmill Villas – a series of three grouped together but individual villas – is the large, functional windmill feature on the outer wall. The three properties – Lilac, Green, and Blue – are clustered on a rocky hillside, each with an outdoor patio with swimming pool, sitting area, and picturesque Aegean views.
Inside, it only gets more charming, with fresh floral decor, open, breezy rooms, as well as colored doors and window frames that correspond to the name of each villa. Refreshing in its design and isolation, it’s a quaint place to get away from it all and enjoy the simple pleasures.
Utterly Mediterranean in its design, decor, and vibe, Villa Mikaela is a pitch-perfect Greek retreat for those who appreciate the finer things in life. Located right on the rim of the caldera, the top feature of this lovely villa is the back patio, complete with large swimming pool and covered seating area – all with some of the best views on the island.
The lushly decorated interior of whites and blues is equally indulgent, with Victorian-era inspired furniture, gauzy curtains that blow in the breeze, and seashell sconces. Arched entryways connect the rooms, of which there are 5 bedrooms, a full kitchen, bathroom, Jacuzzi, and more.
San Nicholas Cave House Villa
Part of the 5-star Chromata Hotel, this private cave house villa is generally considered to be the best hotel villa in Santorini. Chromata pulls out all the stops, offering top-notch butler service and modern comforts like AC and WI-FI.
Initially a private home, the two floors of the San Nicholas Cave House Villa have their own bedrooms, and some of the bathrooms feature heated Jacuzzis. But naturally, in an environment like that, it’s the outdoor terrace – with cold plunge pool, wooden sundeck, alfresco dining, and stunning views – that steals the show.
It’s easy to pamper yourself on Santorini, but Nafsika Estate takes it to a whole new level. This expansive 350-square-meter clifftop estate features five bedrooms, large dining and living rooms, and a full kitchen (although you may want to leave the cooking to your own executive chef). In addition, Nafsika provides private butler service to attend to your every need.
But as with most Santorini villas, it is the terrace area that is the stand-out feature. Located on the lower floor but accessible via both interior and exterior staircases, the large, stone-paved terrace features a large swimming pool, sunning areas, and unbeatable views. And did we mention there’s a private helipad?