Castellina in Chianti

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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

With rolling Chianti hills all around, this traditional villa couldn't feel more Tuscan if it tried. Comprised of a main house and three en-suite bedroom cottages, it's perfect for a large family getaway. While the bathrooms could do with an update, and some of the interiors feel dated, it's all beautifully cared for. Kids will love you for the private pool with dive board –⁠ a fifty-metre flip-flop from the main house. There's also a bocce court and a ping-pong table, and you're welcome to pick fresh vegetables and eggs from the gardens and chicken coop. Location-wise, you're just 5 kilometres from the traditional Chianti towns of Radda and Castellina.

Chianti Memories

With majestic views across rolling hills and olive groves, this home makes it easy to enjoy the magic of Italy. Set within a working winery, you’ll be treated to an authentic taste of rural life along with all the essentials you could need to slow down and spend quality time together. There’s a private swimming pool and a terrace for alfresco dining. The rooms are set across the main house and two independent apartments – making this a great option for groups looking for space to stretch out. Your host can help organise a range of sweet extras such as private chefs and guided tours. Plus, there are beautiful hiking trails straight from the door and it’s just a short drive to the historic towns of Castellina and Radda, as well as the city of Siena.

The Tuscan Muse

Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright interior, where farmhouse simplicity meets elegant design in the living room. With its giant hearth, plump sofas and tiered chandelier, this is the perfect spot for socialising over a glass of wine or curling up by the fire with a good book on cooler nights. With four comfortable bedrooms boasting postcard-like countryside views and a farm-style kitchen full of traditional charm, you’ll have everything you need to make yourself right at home. Head outside to take cool dips in the pool, or sit back in one of the many sun loungers while taking in the spectacular hillside views. Wander around the vineyards, visit Castellina in Chianti (less than ten minutes away by car), then come back home for a barbecue under the pergola paired, naturally, with a glass of Chianti. 

First Of The Summer Wine

This cosy apartment is located in the heart of historic Fonterutoli, surrounded by beautiful Tuscan countryside. Spend your time visiting local vineyards and wineries, or take a day-trip to Siena. The apartment has a classic Tuscan stone facade, which adds to the charm. Inside, you’ll find a fuss-free home that’s equipped with everything you might need for a short break. We think the best feature is the outside area, where you can sit in the shade of the trees and admire the stunning view. 

Wild Onion

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

In the quaint village of Lecchi in Chianti, this semi-detached cottage is part of Montebuoni, a Tuscan hamlet with stunning views of Chianti Classico's vineyards. While the little cottage and its private Mediterranean terrace are all yours, the swimming pools, tennis court and vast gardens are shared with other guests staying on this small resort. Inside, the space presents an authentic Italian countryside set-up with classic designs and contemporary touches to ensure comfort and functionality. It's worth noting that at full capacity – one guest will sleep on the sofa bed in the living room here. You'll find Montebuoni's village centre 4 kilometres away, and day trips to Siena, Florence, and San Gimignano are also easily accessible by car. 


Tuscan Whisper

This 19th-century Tuscan farmhouse that sits 450 metres above sea level has been brought into stylish 21st-century style, all while retaining its rustic charm and characterful Italian romance. Featuring its original windows and tall beamed ceilings alongside contemporary decor, it’s a space that’s been reimagined with rest and relaxation in mind, not to mention a showstopping outdoors that is certain to have you basking in its beauty from dawn till dusk. 

Covering 1,200 square metres of land, the home’s terraced gardens are as expansive as they are stunning. Spend afternoons taking dips in the private pool before sunning yourself on one of the loungers, relishing the scent of the citrus and olive trees perfuming the air. When hunger calls, make your way to the white-draped pergola and fire up the barbecue for a memorable alfresco feast. As the sun begins to dip behind the surrounding hills, watch the stars come out one by one over a glass of wine before heading back inside for a dreamy night’s sleep. 

Should you wish to venture out for a day of exploring, you'll find the medieval village of San Donato a stone's throw away, while Barberino Tavarnelle is also just a short drive from your home. Alternatively, take the scenic Chiantigiana road that links the Chianti area, stopping off in Siena (about 40 km) and Florence (about 30 km), as well as the picturesque towns of Radda, Gaiole, Greve and Panzano, each boasting a wealth of stunning landscapes, historic churches and Renaissance villas. 

Tales of Sunsets

If you’re searching for somewhere to escape the hustle and bustle of everyday life, this Tuscan villa will be right up your street. Ideal for larger groups of friends or family, the countryside location is as peaceful as it gets. And with sunny spots for alfresco dining and a private pool, making the most of the Mediterranean climate is a breeze. Despite the location, you’ll find you’re only a few minutes’ drive from bustling San Donato, while the wine towns of Greve, Radda, and Castellina are within easy reach.

Chianti Nights

If you’re in search of a rustic retreat in the heart of Chianti Classico, this home delivers a sweet solution. You can enjoy stunning views across olive groves, vineyards and rolling hills. There’s a private pool for leisurely afternoon swims, a shaded pergola for evening meals and a billiard room for family-fun and games. The rooms are spread across the main house and an adjacent annexe – providing plenty of space to stretch out and socialise. You will need a car to get around here, but it’s just a short drive to Castellina in Chianti, while Siena and San Gimignano are both within easy driving distance. 

Classic Moments

You've got all the perks of a private home combined with the palatial shared grounds of a hamlet at this apartment complex nestled between the Chianti villages of Panzano and Castellina. The views of the rolling hills and iconic cypress trees are delightful from the estate's shared swimming pool. But if you're after more privacy, the panoramas from the apartment's private terrace are just as impressive. Besides a restaurant in the neighbouring village of Piazza, there are no local amenities to walk to. You'll need a car to explore but prepare for a hilly, uneven drive at times.  

Cheers to Chianti

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