Montalcino

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Boasting traditional Tuscan charm, this countryside villa welcomes up to ten guests, making it an excellent choice for a family or group of friends looking for a restful getaway. Inside, there’s plenty of space for the group to spread out, then come together for meals in the garden. The private pool is sure to be a hit, and the covered terrace is an ideal spot to enjoy a tipple or two. Buonconvento is the closest village, but if you’d like to explore further afield, Siena is easily reached by car.

Green in Bloom

Enjoy the beautiful views of the valley, countryside, and forest from this renovated home's balcony or relax in the small, terraced garden area. This place has a hot tub too in the stone-built cellar, accessed from steep stairs in the living room (there's a bathroom down here too). If you're looking to cook elaborate meals, we should mention that this home just has a kitchenette. Still, there's a bakery 200 metres and a restaurant and bar 50 metres away, as well as a grocery shop 500 metres from this home in Seggiano. Further afield, the pretty town of Montalcino is 23 kilometres away.

Blue Umber

Old collides with new at this secluded villa in the middle of the south Tuscan hills. Days can be spent hopping between the vineyards of the Val d’Orcia or day-tipping to the UNESCO village of Castiglione d'Orcia, a short drive away. This Tuscan farmhouse is surrounded by forest-clad hills, creating a beautiful view from the myriad terraces and patios where you can dine and recline. A private pool awaits for hot days and there’s a barbecue with a view. Oodles of space inside allows big groups to spread out – across the cosy farmhouse living room, the family snug and a vast chill-out room with a teepee and boho-style lounge areas. 

Artistic Retreat

Located in a peaceful and picturesque spot in rural Tuscany, not far from the city of Grosseto, this charming villa is ideal for those looking for a back-to-nature break. There are plenty of hiking, cycling and horse-riding trails in the area, ideal for sunny days discovering vineyards and olive groves. At this home, you'll be surrounded by green and leafy views, and you won't be short of wonderful places from which to view them, with a hot tub, private pool and a lovely dining terrace that's perfect for evening feasts.

The Old Turnstile

Traditional character and contemporary touches collide in this Castelmuzio townhome. Built into the ancient city wall, it has a sense of history and grandeur that we can't get enough of. A working fireplace divides the dining area from the kitchen, while cosy bedrooms beckon after a long day – our favourite is the top-floor suite with its clawfoot tub. Outside, a sun-kissed terrace is the perfect spot to enjoy a morning coffee. There's also a private plunge pool. As for location, you'll be in the heart of the Val d’Orcia. Florence, Siena, and other Tuscan gems are within driving distance.

Cypress & Fig

If you love the artsy side of life, you'll thrive in this contemporary loft. Colourful art pieces stand out, with some splashes of colour added by the feature walls. Natural light pours in through the large kitchen windows – the perfect chance to watch the morning birds fly by. You even get a lovely view of the courtyard from the bedroom too. 

Spend the day at Constanti winery – this is where your host works, so she will be more than happy to give you a tour of the place. Beautiful vineyards surround the loft and a wide range of wineries to sample some of the tastiest glasses of red.

Return home to sit at the dining table while the scent of a home-cooked Italian meal fills the room from the nearby kitchen. After you've eaten, pick a book off of the shelf, and snuggle up on the sofa while the moonlight shines through the windows. Pop the TV on for background noise or simply enjoy the peace and quiet that Montalcino brings.

Artistic Grapes

Located in the Tuscan countryside, this impressive estate is an excellent choice for a couple of large families looking for an easygoing stay. Set across a main building and two guest houses, the residence, dating back to the 1600s, has been carefully restored and boasts fantastic views of Val d’Orcia. Although the traditional interiors may not be to everyone’s taste, the space is functional and perfectly suited to group dining and relaxing. Need a hand planning activities? Your host provides a wide range of experiences from truffle hunting to wine tasting – all on your doorstep.

Titiro Toscano

This villa has space for the whole family to spread out and get comfortable. With a games room and a private pool, there's never a dull moment here – and that's not even counting the many terraces where alfresco dining will no doubt be on the cards. Inside, you'll find a kitchen, dining room, and a living area on each floor. Nearly every room boasts exquisite views of the Brunello vineyards and surrounding countryside. You're also in a great position to explore the Val d'Orcia. Siena, Montepulciano, and Bagno Vignoni are all within driving distance.

Brunello Beauty

This sprawling estate in Tuscany is the stuff that dreams are made of. Composed of the main farmhouse, two outbuildings, and a shared hall, along with plenty of outdoor space, it's perfect for large groups planning an escape to the Italian countryside. 

There are plenty of original features to admire, from the stone exterior to the arched brick doorways and vaulted wooden ceilings. With two kitchens and two indoor living rooms, everyone can make their own schedule and relax in style. Out in the garden, you'll find a sparkling swimming pool that invites you to cool off and plenty of sun loungers where you can catch some rays. And, when evening rolls around, the whole group can gather under the pergola for a fabulous alfresco dinner straight off the barbeque – don't forget the prosecco. 

It would be easy to while away your days without leaving this fabulous estate, but the rolling Tuscan countryside is waiting just outside the walls. You can drive to the medieval walled town of Lucignano in under twenty minutes, and admire the stunning views from its hilltop location. And, if you fancy a day trip, you can drive into the city of Siena in half an hour, or arrive at romantic Lake Trasimeno in forty minutes. 

Trip To Tuscany

Fall in love with the timeless charm of Tuscany from this home perched on the hills of Val D’Orcia. Outside, days can be spent by the saltwater pool and lounging under ancient oak trees. Upon arrival, you will be gifted with four bottles of wine from the estate – setting the tone for an unforgettable Italian stay. Housekeeping is available for an additional fee along with a range of extra services – including private chefs and local tours. It’s worth noting there is an unpaved track leading to the entrance of this home, but you will find it’s just a twenty-minute drive to Castiglione D’Orcia, while Montalcino is just a little further afield. 

Valley of Heaven

This Tuscan home is located in the picturesque village of Monticchiello. Comprising a manor house and separate cottage rented as one, it’s a great choice for a group getaway. The garden is the star attraction here, with its views of the Tuscan countryside. And if you want a relaxing start to the day, your host can provide breakfast to enjoy at the alfresco dining table. We love the exposed beams and brick archways, although the traditional decor may not be to everyone’s taste. Location-wise, you’re surrounded by rolling hills and vineyards, with the historic city of Pienza just under 4 miles away.

Rolling Hills Retreat

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