Greve in Chianti

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Entertainment

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Kitchen

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Kitchen & Dining

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Ironing Board

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Bedroom & Laundry

Private Pool

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Wellness & Fitness

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Private Parking

Parking Available

Parking & Access

Patio / Terrace

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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

Library of Books

Pool / Snooker Table

Bathtub

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Cooking Essentials

High Chair

Kettle

Stove

Toaster

Black-Out Blinds

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Cot / Crib

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Paid Parking On Premises

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Balcony / Patio

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Sun Loungers / Beach Chairs

Mosquito Net

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Fire Extinguisher

First Aid Kit

Set high above the Chianti hills, this sprawling Tuscan villa offers an authentic slice of rural Italian life. Inside, it’s all terracotta tiles, timber beams and arched stone doorways — with cosy corners for reading, a grand hearth for gathering, and space for up to 25 guests across the main house and three separate apartments. Outside, you’ll find gardens for long lunches, shady terraces, and a hillside pool overlooking the vines. With Florence and Siena both within easy reach — and charming villages like Panzano and Greve just around the corner — it’s a peaceful base for exploring the region at your own pace.

The Tuscan Escape

Piano

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Heated Towel Rail

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Balcony

Carbon Monoxide Detector

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Live out your Tuscan dreams at this verdant estate in Chianti. Surrounded by vineyards, the garden is the perfect spot to unwind during the day, whether by the pool or under the shade of the pergola's flowering plants. In the main villa, exposed wooden beams and stone floors take you back to an Italy of long ago, and we love the farmhouse kitchen. But that's not all – there's a separate farmhouse, cottage, and an independent studio hiding on the grounds, offering guests their own space. With a gym and jacuzzi, it's easy to while away the days at home, but it's worth driving the twenty minutes to the town of Greve to sample some of the region's famous produce.

Hidden Villa

Private Washing Machine

Private Dryer

Outdoor Pool

Fireplace

Free Parking On Premises

Sun Umbrellas

In a prime spot for exploring the vineyards and wineries of Chianti, this nine-bedroom villa sets the scene for a memorable holiday. The accommodation is spread over a series of stone farmhouses near the River Greve, each one packed with traditional Tuscan character (think timber beams and rustic tiles). There’s lots of space to spread out and socialise (great for a group getaway), plus a picturesque pool and garden for gathering in the Italian sunshine. You can embrace the pace of life in the country, and still stay close to shops and restaurants in nearby Panzano, as well as being day-trip distance from historic Florence.

River & Vine

Welcome Hamper

Immersed in the natural beauty of the Chianti hills, this home opens its doors to a magical stay with idyllic views. Consisting of a main house and three independent apartments, this is the perfect setting for families and groups in search of space to stretch out and spend quality time together. There’s a swimming pool for refreshing dips and a gym with a Turkish bath for all your wellness needs. Plus, your host can help organise sweet extras like massage treatments, yoga sessions and private chefs. You will need a car to get around here, but it’s just a short drive to hilltop villages, ancient castles and hiking trails. 

The Moon Sanctuary

Perfect for large groups and several families travelling together, this home comprises four separate apartments. Smaller groups can enjoy their own space before everyone comes together to make the most of features like the beautiful dining table and the excellent outside space. There’s an alfresco dining space with a barbecue and stunning grounds with a swimming pool and solarium. In terms of location, you’ll be able to explore the vineyards and wineries of Chianti – why not ask your host to arrange an excursion? 

The Charms of Chianti

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Parking On Premises

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Outdoor Kitchen

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

Those seeking a rustic getaway in Italy will adore this home. It comprises a converted farmhouse and barn in a beautiful spot in the Chianti Hills, surrounded by vineyards and olive groves. It’s between Florence and Siena, so you’ll have plenty of choice when it comes to planning day trips. The villa boasts an infinity pool overlooking the valley, and a panoramic terrace where you can dine alfresco. The kitchen will delight home cooks, but your host can arrange a private chef if you want to leave it to the professionals. 


Cypress Sky

Surrounded by rolling vineyards and olive groves, this 15th-century Chianti estate blends historic charm with contemporary luxury. Inside, each of the nine bedrooms features unique murals by artist Simone Boni and handcrafted Tuscan details. We love the outdoor pool overlooking the countryside and the peaceful patios perfect for sipping a glass of local wine. Meals can be shared under the pergola or around the rustic indoor dining table. While the estate feels blissfully secluded, you're just minutes from Greve’s town square, hilltop villages, and world-renowned wineries. For a true taste of Tuscany, it doesn’t get much better than this.

A Tuscan Beauty

Bread Maker

Sauna

Sitting atop the Chianti hills overlooking the Vignamaggio Valley, this stone estate blends traditional Tuscan charm with modern comforts. It’s perfect for a large group, with a main villa and a renovated barn offering three apartments. While the apartments suit guests seeking privacy, the outdoor terrace is ideal for sharing Tuscan meals together. Relaxation is a priority here, with an outdoor pool, an indoor pool with a hydromassage tub, plus a chromotherapy and infrared sauna. The villa is just 800m from Panzano, with archaeological sites, medieval castles, and monasteries in nearby villages. This is the perfect spot for hiking the Tuscan hills or visiting one of the many vineyards that this region is known for.

Tuscan Hues

Cafetiere

Pod Coffee Machine

Jacuzzi

Multiple Sets of Keys

Herb Garden

There are few more picturesque places in the world than the Tuscan countryside and this gorgeous stone villa in the Chianti hills is the ideal home from which to admire it in all its splendour. Guests will be treated to stunning views of the unspoilt landscape, regardless if they're reclining in a lounger by the 6x12m swimming pool, sitting in the huge covered alfresco dining area or wandering through the large garden. The interior is just as attention-worthy, too. Split into four separate apartments with their own kitchen and living rooms, there's terracotta tiling and wooden ceiling beams throughout that lend a rustic feel, but there are a few modern additions that are sure to be appreciated — not least the private spa complete with a sauna and a hot tub. It's the sort of property where relaxation is the order of the day, but if you ever fancy an excursion somewhere, the cities of Florence and Siena can both be reached in the car in an hour or so.

Casa Superiore

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Let the rosé chill in the fridge and let the red breathe; you’re in the heart of Chianti here, where vineyards sprawl down the hillsides and wine tasting is a way of life. The charming stone villa is tucked between hills and meadows and surrounded by deep green forest. Follow the winding stone pathways through the grounds to a summer house, a pristine swimming pool set in the lawn and a secret gym and Turkish hammam in the outbuildings. Take a seat beneath the wooden pergola and enjoy an evening drink as the sun sets. There’s rustic outdoor dining set up here too.

The main villa, cottage and barn are all tradition meets modernity with wood beams above and terracotta tiles underfoot. Gather the group in the main lounge where a solid stone fireplace takes pride of place alongside a grand piano. The kitchen is like a cross between a professional restaurant's, with a steel range cooker, and an Italian farmhouse kitchen with its rustic wooden table at the centre. Bedrooms are just as charmingly rustic for a quiet sleep to the sounds of the countryside.

Rusticana & Viticulture

Desk

Free Parking

Enjoy a tranquil Tuscan getaway at this wisteria-draped villa, which has been beautifully converted from a historic mill. The river that once powered the mill passes nearby, the sound of flowing water adding to the sense of serenity as you gaze across the garden’s sun-kissed greenery or lounge beside the pool. Indoors, the rooms are cosy and characterful, where original details like exposed brickwork and timber beams have been paired with modern comforts. We wouldn’t blame you if you stayed right here for your entire holiday, but this villa is also an ideal springboard for seeing more of Tuscany’s treasures, from romantic vineyards to Renaissance towns.

Wisteria & Wine

Sound System

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Blender

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Vacuum Cleaner

Step back in time and experience this Tuscan home, a beautifully restored estate dating back to around 1000 AD. This luxurious countryside escape has a private riverside beach, a swimming pool and plenty of areas to relax and dine in the sun. Inside, another highlight is the grand dining room which showcases the well-preserved remains of a 4th-century kitchen. The accommodation is divided between the main villa with four en-suite bedrooms and two guest houses offering additional privacy and space. This home is perfect for families or friends seeking a tranquil retreat in the heart of Tuscany, a short drive from the medieval town of Greve.

Cypress Reflections

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

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

Wine Cellar

Tuscany's rolling hills are your backdrop at this Chianti villa. Once the estate's wine storeroom, this home has been given a contemporary makeover – all while maintaining its charm and character, of course. Each bedroom is as comfortable as the next, although our favourites are the two main suites – one has a freestanding bath, the other a Jacuzzi-style tub. But it's the outdoor spaces that make this home really shine. There's a private pool open during the summer, a terrace with breathtaking views of the Chianti countryside, and acres of private vineyards and olive groves to amble through. Fancy a day trip? Greve, Siena, and Florence are all less than 30 kilometres away.

Vintage Vinery

Nestled on an estate alongside two other villas, this charming home has tranquillity running through its core. Boasting indoor and outdoor pools, you can relax and swim whatever the weather, while sun seekers will adore the outdoor space adorned with loungers and alfresco dining spots. If you can tear yourself away from the views of the Chianti hills, why not ask your host to arrange a vineyard visit? Or to explore alone, it’s just a few minutes to the village of Panzano where eateries and shops await for a taste of authentic Italy.

Chianti Crush

This traditional Tuscan home opens its doors to the natural beauty of the Chianti region. Nestled amid the trees, the private garden lends itself perfectly to lazy days by the pool. You’ll also find plenty of shady spots, family-friendly rooms and the welcome addition of an independent cottage with its own kitchen and one bedroom. Guests can enjoy a range of extra services here, including wine tastings and private chefs, plus it’s just a short drive to the nearest amenities – Radda in Chianti is 8 kilometres away. 


The Ode to Beauty

Courtyard

This grand stone villa looks the perfect part in a region known for its Renaissance history and castles. Located on a gentle hillside slope, this 16th century home sings of rural Tuscany. With its two floors connected by an external staircase, you can easily dip in and out of its beautiful beamed main room and bedrooms and into the gorgeous sunshine. Outside, a covered dining pergola, panoramic terrace, and raised pool garden offer views from every angle, celebrating country living amidst the home’s surrounding woodlands, olive trees, and endless rows of vines. Taste Tuscany's infamous Chianti grapes with an inclusive tour and guided tasting at the Castello d’Albola and explore the hills’ rustic trails and hidden paths on horseback. Discover the nearby ‘road of the castles’ and live out your own royally decadent stay at this home that’s a true feast for the senses.  

Stonehill Vines

Overlooking the Tuscan countryside from its hillside position, this rustic villa boasts some incredible views – best celebrated from the outside dining area and elegant infinity pool. We think it's a great fit for families with a lovely private garden as well as flexible sleeping arrangements – the twin beds can be converted into doubles upon request. Keen cooks will love the modern chef's kitchen for preparing alfresco suppers – though if you feel like dining out, the nearby village of Volpaia and the market town of Radda are both just a short drive away. You will need to hire a car to get around here, and the drive will often be hilly and uneven. 

The Olive Tint

Playground

Wine Cooler

Lift Access

Breakfast Included

Alarm System

The ultimate Tuscan getaway starts at this villa in Radda. Boasting a private pool, a gym and wellness area, and scenic views of the surrounding vineyards, you'll have everything you need here to unwind in style. We love the mix of contemporary design and historic elements like vaulted ceilings and stone archways. Even more, we adore the complimentary extras, such as tastings in the wine cellar, welcome dinners, and a continental breakfast buffet. When you're not relaxing at home, why not spend the day exploring? Castello di Brolio, Siena, and other Tuscan gems are all within driving distance.

Stonehaven

Boasting indoor and outdoor pools and views across the Chianti hills, this home is a true slice of paradise. Set on an estate alongside two other villas, you’ll find an elegant home with plenty of space for all guests to spread out over three floors. Each bedroom enjoys an en-suite, providing privacy when needed, while outdoors you can gather together for alfresco dinners under the sun. Locally, it’s a short drive to the centre of Greve, or the village of Panzano is a mere 800 metres away, where restaurants and shops await. 

Chianti Spirit

At the top of a winding private road, past the beautiful orchards and fields of cypress trees typical of the Chianti region, this hilltop villa awaits. Over 500 years old and beautifully restored, this remarkable home offers plenty of home comforts both indoors and out – two living rooms, a spacious kitchen and four bedrooms each with an ensuite bathroom are evident inside, while multiple outdoor living spaces, a pool and a large private garden feature prominently outside. Local wineries, scenic hikes and historic villages are all around, waiting for you when you’re ready to venture out – or if you’re up for a longer journey, Siena and Florence are both an hour’s drive away.

Chianti Hillside

Hammock

Security System

Immersed in the natural beauty of Tuscany, this home sets the tone for an idyllic Italian escape. Outside, days can be spent lounging by the pool, swaying in the hammock and sipping drinks on the terrace. You'll be serenaded by the soothing sound of the river in the distance and there's a barbecue for alfresco dining. Inside, the rooms are set across the main house and two independent annexes – making this a great option for groups looking to stretch out and spend quality time together. We recommend hiring a car to get the most out of your stay, but it’s just a short drive to the nearest amenities in Tavarnelle, while the Antinori Winery and San Gimignano are both within easy driving distance. 

Kind Love

High up in the hills of Chianti sits this magnificent eighteenth-century residence, flanked by olive groves, rose gardens and lemon trees. The sublime archway structures harken back to the traditional Italian palazzo, and the interiors – prizing terracotta tiles and antique furniture – have a distinctly regal feel. With grounds that sprawl out over multiple hectares and rolling hills surrounding you, you’ll feel like royalty staying here. The dining room is prime for opulent banquets, while the arched patio and the poolside area will answer all of your relaxation needs. When the sun heats up, head down the terracotta steps for a cool swim under the Mediterranean sun. Even better, you’ll be surrounded by the lush vineyards and beautiful food of the Chianti region. What more could you want?


Chianti Classico

Ice Machine

With a serene garden, beautiful views and a private pool, this home welcomes you to slow down and savour the magic of Italian living. There’s a wellness area with a Turkish bath and a sauna, as well as a wine cellar – making it easy to settle in and unwind. Upon arrival you’ll be treated to a light dinner and wine tasting, and your host is on hand to help organise a range of extras – including spa treatments and private chefs. You will need a car to get around here, but it’s just a short drive to the nearest shops and restaurants in Radda in Chianti, while Siena and San Gimignano are also within easy driving distance. 

Dream of Light

Vineyard views, vintage decor, and verdant surroundings give this Tuscan villa an abundance of charm. We're especially fond of the outdoor space. You can take a dip in the private pool, relax on the sun loungers, or dine on Italian cuisine in the loggia-style courtyard. There's even more space to relax indoors, from the cosy library to the sumptuous main suite with a Jacuzzi-style bath. When you're ready to venture out, you're just a five-minute drive from Greve and close to many other classic Chianti market towns.

Sprig & Stone

Nestled in the heart of the Chianti countryside, this villa offers a tranquil escape from the hustle and bustle of daily life. We love the traditional Tuscan touches in this home, and with it being split into two apartments, it’s ideal for extended families or friends who want to enjoy a little privacy occasionally. Outdoors, the private pool, sun-kissed terraces and sweeping views all jostle for attention – it’s just the spot to relax with a glass of local wine. Locally, the village of Lucolena is within walking distance and boasts a well-stocked shop and bar, or further afield, it’s a mere twenty-minute drive to Greve. 

Vines & Lavender

This home is in the heart of Chianti country, just outside of pretty Panzano in Chianti. It’s been crafted from Tuscan stone and boasts a watch tower with a romantic bedroom. You’ll have a private pool to cool off in, and access to a Jacuzzi and sauna when you need to take your vacation relaxation to the next level. We love the terraced gardens and the wonderful views of the vineyards and countryside. You’re only a twelve-minute drive from Greve in Chianti, and Florence and Siena are also within easy reach for day trips – we’d definitely recommend hiring a car to make the most of your stay. 

The Maestro's Daughter

Shared Pool

Ever dreamed of living the dream in the Tuscan countryside, with blue skies and those signature cypress and olive trees all around? Well dream no more. Nestled in the heart of the Chianti region, this two-bedroom villa has everything you need for a comfortable stay. Swimming pool, check. Spacious, luscious garden, check. Rustic interior and furnishings, check. And to top it all off, the location celebrates the best of both worlds: there are plenty of things to see in the surrounding countryside, like the Palagio Ricevimenti castle – or it’s a simple drive to Florence, the cradle of the Renaissance.

A Tuscan Idyll

Ceperano is a charming Tuscan farmhouse that has been restored to a high standard and can accommodate up to 14 guests. The property is situated in the heart of the Chianti region, surrounded by olive groves and vineyards, providing a tranquil retreat for families or groups of friends. The farmhouse features four apartments, each offering comfortable traditional furnishings, with three separate kitchens to cater for all dining preferences. Ceperano boasts several furnished terraces and a bamboo-shaded pergola with stunning views, perfect for al fresco dining. The private pool is set in a fenced lawned area, ideal for children playing nearby while adults relax on loungers. Five bedrooms offer flexible sleeping arrangements as they can be either doubles or twins, with plenty of bathrooms throughout the property. Ceperano is within walking distance of the lively town of Radda and an easy day trip from Siena, Florence and San Gimignano.

Cicerone

Workplace

Free Parking On Street

Elegant and unique, this home makes for an excellent base in Tuscany. It’s in the village of Impruneta on the outskirts of Florence, surrounded by countryside, olive groves and vineyards – it also borders the Chianti Classico region. The centre of Florence is only 13 kilometres away, making day trips a breeze. The decor is traditional, with antiques at every turn, so it may not suit everyone. But for a break to Italy that feels a little like stepping back in time, it’s a great choice. 

The Falling Stones

Shared Washing Machine

Shared Dryer

Gated Community

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

Sitting on the hillside in Chianti's countryside, this apartment is part of a small collection of cottages and apartments. Typically Tuscan, the interior may be a tad dated – and you'll have to share laundry facilities – but it'll suit those craving a bit of character. You'll also have access to all the on-site amenities, including a communal terrace for alfresco dining and a shared swimming pool open from May to September. We highly suggest hiring a car here, as you'll want to get out and about to explore the local area. Vineyards, charming hamlets, and sightseeing hotspots like Florence and Castellina are all within easy reach.

Chianti Rosemary

Situated on the first floor of a traditional Tuscan stone building, this apartment puts you right at the heart of rural Tuscany, surrounded by glorious rosemary bushes, grape vineyards and olive groves. Here, you'll enjoy access to the site's fantastic communal facilities, including a terrace area with seating where you can gaze out at the countryside views, plus an outdoor swimming pool that's surrounded by loungers for afternoon naps. Inside, you'll find traditional Tuscan decor that makes the home feel warm and welcoming.

Grape Juice

Juicer

Outdoor Bathtub

This converted mill is charmingly modern, with hints of its history still present – our favourite being the original kitchen which dates back to the 4th century A.D. This stylish villa offers a host of amenities too, including a private pool, a pizza oven, a daily cleaning service and complimentary grocery delivery on arrival. If you’re visiting as a large group, you’ll enjoy the layout here, with a main house and two separate annexes. The outdoor areas are the perfect spots to come together after some one-on-one time, especially to share a chef-prepared dinner alfresco, which your host is happy to arrange upon request. And when you’re ready to explore, you’ll find hiking routes and vineyards within easy driving distance.

The Stone Mill Escape

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