Villa Montessito

As soon as you walk through the door of Villa Montessito, your shoulders drop.

This ultra-luxurious villa, which is perched high on a hillside just above Mykonos Town, has a horizon that extends from the old port to the distant line of islands, giving the impression that it is floating above the Aegean. At dusk, everything slows down as the sky turns copper, rose, and deep violet in front of you. At night, the sea is filled with tiny moving lights from boats and yachts. Montessito stands out among Mykonos Villas as one of the few residences that blends a genuine five-star rating with a feeling of comfort, seclusion, and coziness.

The light is the first thing you notice when you wake up in one of the ten bedrooms. Even before you stand up, you can see the bay’s curve and the whitewashed homes of Chora below thanks to floor-to-ceiling openings. No one has to sacrifice comfort thanks to the main villa’s seven double bedrooms, all of which have views of the sea and private bathrooms.

The additional double bedrooms in the guest house, which has its own separate entrance, are ideal for staff members traveling with you, older kids, or friends who would like a little more freedom. Montessito is perfect for large family get-togethers, birthday vacations, or those once-in-a-lifetime celebrations where everyone you love is finally under one roof because it can comfortably accommodate up to twenty guests.

The large pool terrace is the focal point of the house. The property’s front is lined with a massive infinity pool that visually spills into the Aegean’s deep blue. This is where life takes place during the day: children playing by the water’s edge, friends meandering between loungers and shaded couches, background music playing softly while someone mixes drinks at the bar.

The terrace transforms into a different kind of stage as the heat subsides. The whole scene in front of you becomes a living painting as the sun sets behind the town and boats silently enter and exit the port. You realize that it has been hours since you last looked at a watch.

White walls, natural stone, soft textiles, and thoughtfully selected furniture that feels opulent but never stiff are all features of Montessito’s sleek, modern island interior design. Large, cozy couches, long tables for late-night dinners, and a fully furnished kitchen ready for a private chef or a self-assured home cook are all part of the main living areas’ communal design. The home theater creates the ideal dark, cozy space for movie marathons after long days in the sun, and the private gym allows you to work out while taking in the scenery.

The property never ceases to astound you when you step outside the main house. Everyone can find their own spot to read, converse, or simply gaze out at the water thanks to the numerous lounging areas. The helipad is perfect for guests arriving by private charter or traveling from Athens or neighboring islands because it allows you to arrive in total privacy and style while completely avoiding the main roads. Overall, it feels like a self-contained compound in the sky that is both close to everything and completely separate from the outside world.

You are only a short distance from the heart of Mykonos, despite the feeling of escape. Depending on traffic and the time of day, Mykonos Town is typically 5 to 10 minutes away by car from the villa. This makes it simple to take a late afternoon stroll through Chora’s lanes, grab a drink in Little Venice, or eat dinner at one of the old-harbour restaurants before heading back to the peace of the hill.

Mykonos Airport (JMK) is normally 15 to 20 minutes away from the property, while Tourlos, the island’s main port, is typically 10 to 15 minutes away by car. A comfortable SUV or a prearranged driver is advised, especially at night or during peak season, as the roads are paved but narrow and frequently steep on the final approach.

Day trips and beaches are equally accessible. Ideal for a swim and a long lunch at a beach taverna, the more sheltered locations, such as Ornos and Agios Ioannis, are usually 15 to 20 minutes away by car. You can visit the well-known party beaches of Psarou, Paraga, and Super Paradise, all of which are comparable distances away, before returning to the tranquility of Montessito. Ornos or the old port, which are both conveniently close to the villa, can typically arrange boat charters to Delos and Rhenia, two of the most unique experiences in the Cyclades.

Montessito stands out among all the Mykonos Villas due to its hilltop helipad location just above town, its uncommon capacity for twenty guests spread across ten bedrooms, and its resort-style amenities, which include a large infinity pool, a private gym, a home theater, and total privacy, all wrapped in a design that feels luxurious yet effortlessly livable.

A stay here is ideal for three straightforward experiences. Go to Mykonos Town one evening for a sunset drink in Little Venice and a leisurely dinner in Chora. Return in time to see the final rays of the sky from your pool terrace.

After spending a few hours at the south-coast beaches (Ornos for families, Psarou for people-watching, Paraga for music) on another day, head back to the villa for a late-night movie at the theater and one last swim outside. On the third day, stay completely local: wake up slowly, work out in the gym while the town below comes to life, spend the afternoon lounging in the shaded lounges and by the pool, and end the day with a private chef dinner on the terrace while the boats follow their paths across the dark water.

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