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If you're a frequent visitor to Tuscany and looking for somewhere that's slightly off the beaten track for your next trip, the medieval town of Cortona is a lovely choice and this apartment on the outer edges will help you see the best of it.

Spread across two floors, the interior is a distinctive mix of period features, such as the flagstone floors and wooden ceiling beams, and modern touches, like the monochrome kitchen and smart grey bathroom. Compared to a lot of other apartments for two, there's a pleasing amount of space inside and nothing feels cramped.

The local town is one that's easy to explore on foot and you'll discover plenty of restaurants and ice cream parlours, plus a couple of museums, during your wanderings. The Basilica of Saint Margaret of Cortona and Fortress of Girifalco are both only twenty minutes away on foot, too.

Noah's Son

This is an exquisitely restored medieval home found on the border between two of Italy’s most historic and picturesque regions, those of Umbria and Tuscany. But like the famous local wines we’re certain you’ll find this villa has done nothing but improve with age. Inside, the rustic interior with its leather furnishings and exposed timber provides a deep sense of comfort, whether you’re gathered in front of the wood-burning fireplace with a glass of red or sat at the writer’s desk in the small library waiting for the muse to strike.

Fortunately, inspiration is not hard to come by. Stepping outside you’ll be stunned by the beauty of the rolling verdant countryside, a permanent backdrop that can be equally enjoyed from the alfresco dining table as from the dazzling pool and sundeck. The atmosphere is only heightened by the numerous trees and flowering plants that seem to frame every view. Add to this easy access to the beautiful lakeside towns around Lago Trasimeno as well as amenities like a home gym and sauna, and it’s fair to say this really is all that you can ask for. 

The Middle of the Journey

Set amidst the verdant greenery of the Tuscan countryside, this elegant home invites you to experience the timeless charm of Italian living. 

And from the moment of arrival, the atmospheric presence of the villa feels inspiring. Formerly a church that belonged to an old noble property, the owners have sensitively restored this building into a home that shines with character and poetic beauty. 

From the traditional features to the art and objects, every detail brings a quality of joy to daily life. And whether you’re gazing at the garden views from the kitchen, sipping coffee on the terrace or soaking in the bathtub, it’s easy to settle in and feel at home here. 

Stepping outside, you’ll discover an idyllic sanctuary – a natural haven perfectly poised for refreshing morning swims, long lunches and sunset drinks. Take a short stroll and you’ll find the village of Pergo is just fifteen–minutes away – there’s a supermarket here for any basic amenities you might need. And for explorations further afield, the picturesque hilltop town of Cortona is just a ten–minute drive away. From here you can meander through the medieval streets, stop for gelato and savour the beauty of the Valdichiana valley. 

A Sweet Symphony 

Close to the cities of Perugia and Arezzo, this cosy bungalow is the perfect base for exploring the Umbria region. With easy access to a motorway, if you rent a car you can explore a lot of the area’s most fascinating hilltop towns with ease. The spacious garden encircles the entire house, offering plenty of green space for the little ones to run around. You’ll also find plenty of sunny spots from which to soak up the views, our favourites being the private swimming pool and patio.

Pastel Daydreams

Nestled on the hills at the foot of Lake Trasimeno, this charming villa is the perfect escape away from the hustle and bustle of everyday life. Ideal for larger groups, there’s plenty of space to spread out and enjoy some quiet time here – and with each bedroom boasting an en-suite, there will be no queue to get ready in the mornings. That said, we think everyone will naturally be drawn to the outdoor space. A private pool, sun-drenched terraces, alfresco dining spots and views across the lake – what’s not to love?

Terra Magica

This rustic-style villa, nestled amid unspoiled swathes of the Italian countryside close to the quintessentially Tuscan town of Cortona, provides the perfect place to slow down, reconnect, and immerse yourself in the laid-back way of life this area offers. In the surrounding area, named Val d'Esse, you will find a wealth of historical, cultural, and archaeological treasures, as well as the eponymous river that runs through the valley and plenty of fantastic local eateries serving traditional delicacies – so there really is something for everyone. 

Inside, the feeling of this home is one of an authentic old farmhouse. Filled with character, charming stone features, traditional detailing, and offering a rustic kitchen at its heart, the home is warm and inviting. Enjoy coming together in these cosy spaces to cook, eat, and unwind in the company of your nearest and dearest. 

Step outside and the pool area provides the perfect spot to take some time for yourself, soaking up the sun as well as the tranquillity of the rural location. As the sun begins to set, experience that elusive sense of holiday bliss as you dine overlooking the rolling green landscape, feasting on regional delicacies and sampling some of the area's delicious wines. When you want to venture further afield, then the iconic towns of Siena, Florence, and Assisi are all accessible for a day trip too.

Under A Tuscan Moon

In the folds of the hills, this home is all about those Tuscan sunsets. Catch the golden hour, as the sun dips below the forest-clad hills, from the terrace where curtains frame the view and dining by candlelight is a delight. Days can be spent drifting from one terrace lounge to another, or swimming laps in the pool – the sun hits the water throughout the day. There are two farmhouse-style kitchens to choose from – one is professional-grade in the basement of the main villa and the other, a smaller affair in the separate cottage. Guests can spread out between both buildings, each with its own living room, and join together for excursions to Cortona, 10 kilometres away.  

Rosemary Breeze

Dating back to the 18th century, this home provides the perfect setting for a dreamy Tuscan retreat – one that’s filled with the majestic beauty of the Italian countryside. And from the moment of arrival, you’ll want to pause to admire the unique charm of this setting. 

Surrounded by trees, the abundant garden fills the house with a wonderful sense of peace and tranquillity – inviting you to put down your bags and make your way inside. 

From the elegant styling, rustic stone and traditional features to the air-conditioned bedrooms (each with its own bathroom), the owners have honoured the building’s heritage whilst integrating contemporary comforts – including a lift to travel between floors. And with an abundance of living space, both inside and out, this is the perfect location to celebrate the simple pleasures of Italian living. So whether you’re enjoying a quiet morning coffee on the terrace, swimming in the pool, relaxing in the shade or sharing Italian-inspired feasts as the stars fill the sky, every moment promises to be enriched by the natural beauty of the surroundings. 

Beyond this private sanctuary, it’s just a short scenic drive to the hilltop town of Cortona, while the region is brimming with opportunities for long hikes, sightseeing, wine tasting and simply admiring the views across the Chiana Valley.

The Main Event

Tucked within seventy hectares of countryside and surrounded by countless rows of olive groves and cypress trees, this charming Tuscan estate is the picture of rural tranquillity. Split into the main house and an independent annexe, the address has retained plenty of its original features – wooden beams, an open-hearth fireplace, stone floors and antique furniture give guests a sense of history. Start your day by pushing open the French doors in the living room and looking out over the neighbouring hills before sharing breakfast in the charming kitchen. 

Stepping outside, the home’s beautiful garden is an ideal sunbathing spot, while the sparkling swimming pool is perfect for cooling off from the midday heat. Find a cosy corner amid the plants to enjoy a cocktail at sundown, then head to the pergola, where an elegant dining table promises an unforgettable alfresco experience. If you can bear to leave your manor, the pretty town of Montepulciano is a short ten-minute drive away. Walk its winding streets and try the rare Vino Noble wine the region is so famous for.

Aglio e Olio

Made for outdoor living and large family gatherings, this home is sure to jump high up on your wishlist. We love the space this home has, and with two apartments independent from the main villa, it’s perfect for extended families where two couples are seeking a bit of added privacy. With traditional interiors, it’s a comfortable place to call home – but it was the outdoor space that caught our eye. Sun-kissed terraces, alfresco dining opportunities, a private pool and hot tub, and all a short drive from the beautiful hilltop town of Cortona. 

Tuscany in Bloom

This contemporary villa set on the edge of Terontola in southern Tuscany is just the ticket for those seeking a serene escape away from it all. Boasting modern interiors, a private pool and sun-kissed terraces, it’s a real gem. But the cherry on the cake? This home has its very own spa. So, if you fancy a sauna or massage, just wander down the steps to the lower ground floor where your sanctuary awaits. Keen to explore? Drive to historic Cortona, sample the local chocolate of Perugia, or bathe in the hot thermal springs at Bagni San Filippo – you’ll never be lost for things to do. 

A Triumph in Tuscany

Frescoed cherubs and exposed stone walls; this villa is the epitome of old Italian charm. It sits in the Umbrian countryside, an eight-minute drive from Castiglione del Lago, on the shore of Lake Trasimeno. Delightful day trips are on the cards with the Etruscan history of Chiusi a twenty-minute drive away and the hilltop enclave of Perugia reachable in forty minutes. 

A big swimming pool sits in the manicured lawn, where the old stone villa seems to admire itself in the water’s reflection. Alfresco dining is set up beneath gazebos that wouldn’t look out of place at a Rennaisance fair and the view is of endless rolling vineyards all around. Two built-in barbecues provide chefs with plenty of room to cook outdoors. 

Heading inside, a warren of archways lead to grand lounges and chandelier-clad dining rooms. Wooden ceiling beams and painted frescos on the walls feel as though you’ve stepped into the 18th century and the kitchen is a vision of old-world charm. This feeling continues in each beautiful bedroom, where four-poster beds are swathed with silk curtains and the two main bedrooms come with free-standing slipper tubs. 

Umbrian Fairytale

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