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The approach sets the tone before you even step inside. Casa Cortona by Stay Awhile Villas is the kind of property that feels as though it has always been here, its stone walls and terra cotta warmth inseparable from the hillside landscape that surrounds it. This is a private residence rather than a hotel, a distinction that shapes everything about the experience. There is no lobby, no concierge desk, no choreographed welcome. Instead, there is the quiet satisfaction of arriving somewhere that feels immediately and entirely yours.
The villa unfolds with the generous proportions of a traditional Tuscan home. Interiors are grounded in natural materials and a restrained palette that lets the architecture do the work. Stone floors, exposed beams, and whitewashed walls create rooms that feel cool and calm even in the height of summer. Living spaces are designed for gathering, with deep sofas, long dining tables, and the kind of open kitchen that draws everyone in. Bedrooms are private and unhurried, with linens that invite late mornings and shuttered windows that frame the surrounding countryside. The outdoor spaces are equally central to daily life here. Terraces extend the living area into the open air, offering long views over the rolling hills and the patchwork of olive groves and vineyards that define this part of Tuscany. Whether you spend the afternoon reading in the shade or preparing an evening meal with ingredients from a local market, the rhythm of the house encourages a pace that is slower, more deliberate, and deeply restorative.
Cortona itself is one of Tuscany's most storied hilltop towns, its Etruscan origins visible in the ancient walls that still encircle the historic center. Narrow streets climb between medieval buildings, opening onto small piazzas where locals gather over espresso and aperitivo. The town's cultural identity is layered and lived-in, shaped by centuries of art, agriculture, and community. Weekly markets offer seasonal produce, local cheeses, and cured meats, while trattorias serve the straightforward, ingredient-driven cooking the region is known for. Beyond the town, the Val di Chiana stretches toward Lake Trasimeno, and day trips to Arezzo, Montepulciano, and Siena are well within reach.
Casa Cortona is not a property that announces itself. Its appeal lies in the way it recedes, offering the space and comfort of a beautifully kept home without the formality of a traditional hospitality experience. Days here take the shape you give them. The house simply provides the setting, and what lingers long after departure is the memory of golden afternoons on the terrace, the sound of cicadas in the late heat, and the particular stillness that only a house like this, in a landscape like this, can offer.
The approach sets the tone before you even step inside. Casa Cortona by Stay Awhile Villas is the kind of property that feels as though it has always been here, its stone walls and terra cotta warmth inseparable from the hillside landscape that surrounds it. This is a private residence rather than a hotel, a distinction that shapes everything about the experience. There is no lobby, no concierge desk, no choreographed welcome. Instead, there is the quiet satisfaction of arriving somewhere that feels immediately and entirely yours.
The villa unfolds with the generous proportions of a traditional Tuscan home. Interiors are grounded in natural materials and a restrained palette that lets the architecture do the work. Stone floors, exposed beams, and whitewashed walls create rooms that feel cool and calm even in the height of summer. Living spaces are designed for gathering, with deep sofas, long dining tables, and the kind of open kitchen that draws everyone in. Bedrooms are private and unhurried, with linens that invite late mornings and shuttered windows that frame the surrounding countryside. The outdoor spaces are equally central to daily life here. Terraces extend the living area into the open air, offering long views over the rolling hills and the patchwork of olive groves and vineyards that define this part of Tuscany. Whether you spend the afternoon reading in the shade or preparing an evening meal with ingredients from a local market, the rhythm of the house encourages a pace that is slower, more deliberate, and deeply restorative.
Cortona itself is one of Tuscany's most storied hilltop towns, its Etruscan origins visible in the ancient walls that still encircle the historic center. Narrow streets climb between medieval buildings, opening onto small piazzas where locals gather over espresso and aperitivo. The town's cultural identity is layered and lived-in, shaped by centuries of art, agriculture, and community. Weekly markets offer seasonal produce, local cheeses, and cured meats, while trattorias serve the straightforward, ingredient-driven cooking the region is known for. Beyond the town, the Val di Chiana stretches toward Lake Trasimeno, and day trips to Arezzo, Montepulciano, and Siena are well within reach.

What strikes you about this Hollywood Hills villa isn't the grandeur itself—it's the way the interiors feel genuinely considered rather than staged. There's a warmth to the design that resists the cold minimalism so many high-end LA rentals default to, with bespoke art and furnishings that feel curated by someone who actually lives with beautiful things, not just photographs them. The outdoor space operates like a private world above the city—pool, hot tub, firepit, a proper BBQ setup—all oriented around that sprawling skyline view that never quite lets you forget where you are. It's the kind of place that suits a group who wants the energy of Los Angeles without surrendering their evening to it, where a night in feels as intentional as a night out.
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Guest
Great place. Would go again
Guest
⭐️ ⭐️⭐️⭐️⭐️. Beautiful home. Very clean! Everything is new and fresh. This house was my favorite, design wise. One thing that Stay Awhile does impeccably well is outfit the homes in such a way that you have everything you might need while staying there. Fully stocked kitchen. Comfortable bedding. Laundry supplies. They do it best. I know when I stay in one of Stay Awhiles properties, I’m going to be comfortable as if I’m at home. And I treat these houses like I’m home. Hands down my go to company when renting. This house specifically had a beautiful very functional outdoor space. The pool and deck area. The outdoor sofas and TV area. Outdoor shower which I definitely used. If you grill, there’s a grill. It’s great. All of it. Great property for their ever expanding portfolio. Another excellent stay, thanks guys!
Guest
Great place! Loved my stay here.
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