Cesena

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Located on a hillside blanketed with ancient olive trees and gnarled grapevines, this wonderful home offers you and your family a chance to get away from it all. Emilia-Romagna boasts some of Italy's best-preserved medieval towns, its finest produce, and its friendliest people – there's little not to love about this less-visited part of the country.

Your hosts have paid great attention to detail to create a home that boasts all the modern conveniences you'd hope to find while employing age-old building techniques to create a traditional-looking property that blends seamlessly with its surroundings. Inside, you'll find tiled floors, exposed beams and vaulted brick ceilings, plus plenty of antiques that lend further credence to the idea that this building could be four or 400 years old.

Beyond the gorgeous interiors, outside is where this home really shines. With over 10,000 sqft of gardens, there's plenty of space for an inviting pool and two covered seating areas, as well as verdant lawns for the kids to play on. The awe-inspiring views over the surrounding landscape are just the icing on the cake. 

If you can tear your eyes away, we'd suggest exploring the charming hilltop villages. You never know when you'll stumble across the best wine or olive oil you've ever tasted. Elsewhere, the historic cities of Cesena and Rimini are approximately twenty kilometres away.

Romagna Gardens

If you’re a large group seeking a sun-kissed Italian getaway, look no further than this expansive estate in Greve. Made up of three villas, each with a private pool and separate outdoor space, it’s the perfect blend to allow sociable time gathered as a group and quiet time when needed. All bedrooms offer en-suites, some open to the bedrooms, with luxurious touches peppered throughout. Oozing tranquillity, the outdoor space offers alfresco dining and views across the surrounding vineyards and olive groves. Locally, you’re just a few minutes from the village of Panzano where local eateries and shops await, while the centre of Greve is just seven kilometres away. 

Tuscan Hilltop

This beautiful home can be found in Reggello, close to Florence and only 4 kilometres from some of the best shopping in Tuscany. It’s a modern home-from-home, cool and comfortable, with a delightful outside space. A private pool sits in a vibrant garden filled with flowers and aromatic plants, where there’s a barbecue for alfresco dining, and an air-conditioned gym. Sliding doors connect the relaxing garden with the stylish villa, with its open-plan living and dining space. You won’t want to leave. 

Giardino Joy

Perched on a hilltop in Arezzo, this home is perfect for a relaxing Tuscan escape. The private infinity pool looks out across the mountains, and there’s plenty of space in the garden to take in the views, dine alfresco or even play a few rounds of table tennis as the sun sets. A separate one-bedroom annexe with its own kitchen and living space offers extra privacy for families or friends travelling together. And with Piazza Grande just a five-minute walk away, along with plenty of bars and restaurants, the location couldn't be better.

Arezzo Window

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind. You can enjoy access to the shared swimming pool and there are plenty of spots where you can sit back and admire the views. It also makes a great base for exploring this beautiful region. From here, its a short drive to the local villages of Lecchi and San Sano, while Siena and Florence are also within driving distance. 

Chianti Sunrise

Surrounded by olive groves and ancient woods, this traditional farmhouse welcomes you to an authentic stay in the heart of Tuscany. 

Located on Pomaio hill with sweeping views across the countryside, this is a wonderful setting to retreat into the heart of nature. And from the moment you arrive, you’ll want to savour the rustic simplicity and charm of this home – it’s the perfect place to connect with the timeless beauty of Italy. 

Families and friends will love gathering here – the communal spaces feel warm and intimate, inviting you to slow down and enjoy quality time together. And whether you’re drinking your morning coffee in the garden, swimming in the pool or cooking in the cosy kitchen, this is the kind of home that enriches daily living. 

Outside, follow the garden path out into the surrounding countryside for an inspiring stroll, or make the short drive into the majestic city of Arezzo – just ten–minutes away. Whether you’re admiring 15th century frescoes and abbeys, or olive trees and vineyards, this home is the perfect setting to celebrate the authentic taste of Tuscany. 

The Terracotta Sun

Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold. Or relax on your terrace or balcony in the private garden. It’s the perfect spot for an Italian feast cooked on the barbecue or rustle up something in the kitchen on the first floor with its marble worktops. If you need to top up on ingredients, then Gaiole, 4 kilometres away, has a selection of shops, as well as restaurants, while the nearest village, Barbischio, 1 kilometre away, has a superb trattoria. 

The Vines of the Vineyard

Traditional and romantic, this charming Tuscan home is in wine country, and we can practically smell the freshly uncorked Chianti from here. Beautiful to look at, both inside and out, and surrounded by lovely gardens, this is the kind of place where everything can just slow right down. Stroll to the pool for a morning swim, laze in the hammock in the shade of the trees, and casually put together delightful meals using the finest local ingredients. Inside, there are tiled floors, shuttered windows and exposed timbers, making for a rustic feel. There's a country kitchen for dining inside, but we're guessing you'll make the most of the covered terrace and eat alfresco each and every day. There’s nothing better than a wine tasting experience in these parts, so we recommend you sample the product at the Castello di Albola winery, just a ten-minute drive away. And if you're tempted to head off for a cultural day out, the stunning Renaissance city of Siena is just fifty minutes away. 

Vino Classico

This home is a true haven nestled right in the heart of Arezzo. With its luscious garden and rustic interior, it's the perfect place to kick back and relax away from the hustle and bustle. 

Step inside, and you'll be enchanted by the traditional touches, from the terracotta tiles to the original fireplace and wooden ceiling beams. Budding chefs can whip up their favourite dishes in the kitchen, using the fresh Italian herbs provided. And, the leafy garden provides the ideal spot for a sundowner – open a bottle of Pinot Grigio and relax on the patio as you make some plans for the following day. 

The hilltop Arezzo Cathedral is not to be missed – admire the painted ceilings before strolling through the medieval town, gelato in hand. The nearby Piazza Grande is one of the most beautiful in the region, and is an awe-inspiring setting for a coffee or something stronger. And, if you want to explore more of eastern Tuscany then there's plenty to see just a short drive away – from vineyards to castles, there's something for everyone. 

Pistachio Pesto

Treat yourself to a relaxing stay at this rustic villa in the heart of Chianti, one of the Old World’s best known wine regions. Fully renovated in 2016, this authentic Italian home will delight even the most discerning guest with its characterful design features – think wooden ceilings and gargantuan stone fireplaces – and comprehensive selection of modern amenities. 

There’s no shortage of activities to keep you busy here – whether it’s relaxing by the pool, playing board games by the fire, or perfecting your forehand on the private tennis court – but we wouldn’t blame you if all you wanted to do was sit back and take in the view. Settle into one of the chairs in the garden and gaze out at the Tuscan hills while your private chef gets to work in the kitchen. When you’re ready to eat, gather everyone round whichever dining table takes your fancy – there are plenty of options here – and enjoy a leisurely lunch under the midday sun before heading out on a gentle hike through the gorgeous countryside. If you want to explore further afield, hop in the car and set off for Radda in Chianti where you’ll find a whole host of authentic Italian eateries, or make your way to Siena – just over half an hour away – and spend the day learning more about the region’s rich history. Back at the villa, your comfy, air-conditioned bedroom awaits, so why not head up and get some much-needed shuteye? We promise this dreamy Tuscan abode isn’t going anywhere. 

Sunflowers & Sangiovese

Amidst the vineyards and olive groves of Tuscany, this winery estate perfectly embodies the magic of its location. Enjoy idyllic views and slow days relaxing by the private pool. There’s an outdoor kitchen with a pizza oven for memorable evenings under the stars. Inside, the rooms are set across the main house and the adjoining cottage – making this a great option for groups and families looking to stretch out and spend quality time together. You’ll also be perfectly placed for adventures across the Chianti Classico region. It's also just a twenty-minute walk into the heart of Greve in Chianti, where you’ll find a great selection of artisan shops, restaurants and patisseries.  

The Vineyard Dreams

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