Buonconvento

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Entertainment

Bathtub

Hair Dryer

Bathroom

Fridge

Kitchen

Microwave

Oven

Stove

Dishwasher

Kitchen Utensils

Cooking Essentials

Kitchen & Dining

Dryer

Iron

Washing Machine

Bedroom & Laundry

Swimming Pool

Private Pool

Wellness & Fitness

Wi-fi

Internet & Office

Air Conditioning

Fireplace

Central Heating

Heating & Cooling

Free Parking On Premises

Free Parking On Street

Parking & Access

Patio / Terrace

Barbeque

Garden

Outdoor

Pets Allowed

Pets

Child Friendly

Other

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

Satellite / Cable TV

Toiletries

Coffee Maker

Espresso Machine

Freezer

Kettle

Toaster

Drying Rack

Vacuum Cleaner

Laptop Friendly Workspace

Free Parking

Parking Available

Private Entrance

Self Check-in / Check-out

Beach / Pool Towels

Outdoor Seating

First Aid Kit

Rustic charm meets modern luxury in this hilltop Tuscan home. Boasting fantastic views of Montalcino, we think the garden is the perfect spot to enjoy the sunshine and fresh air. Entertain yourself with a dip in the private pool, play a game on the bocce court, or tuck into an Italian feast on the terrace. Step inside and you'll find seven en-suite bedrooms and a living space brimming with traditional character. Siena, Buonconvento, and other picturesque towns are within driving distance, making it easy to explore. There's also the option to arrange wine tastings, private dining, horseback riding, and other experiences – it's no wonder this home caught our eye.

Hilltop Aria

High Chair

Cot / Crib

Outdoor Pool

Desk

Sun Loungers / Beach Chairs

Sun Umbrellas

Set amidst rolling Tuscan countryside, this villa promises an escape from it all. With a mix of modern and traditional interiors, there’s something to appeal to all tastes here, and plenty of space for up to ten guests to spread out comfortably. Outdoors, the private pool takes centre stage, while sun-worshippers will be delighted with the expanse of terraced areas and garden from which to soak up the rays. For a day out, nearby Siena is well worth a visit for its beautiful buildings, historic sites and abundance of eateries offering a true taste of Italy. 

The Valley's Mine

Ping Pong Table

Garden Games

Welcome Hamper

Nice to haves

Situated in the Val D’Orcia, with stunning views of Montalcino, this home has an idyllic, secluded setting. There’s a pool to cool off from the Tuscan weather, as well as a barbecue, a wood-burning oven, and several relaxation areas. Ideal for families or friends, the accommodation consists of the main house and a one-bed guest barn. We love the mix of modern with the kitchen and the character features such as the barrel-vaulted ceiling in the dining room. Location-wise, you’ll be near Buonconvento, described as one of the most beautiful villages in Italy. 

Tranquil Tuscan Retreat

Heated Towel Rail

Rain Shower

Pod Coffee Machine

Hangers

Ironing Board

EV Charger

Courtyard

Outdoor Shower

Mosquito Net

On a hill in the beautiful Val d’Orcia, this traditional stone villa looks out over the undulating countryside. It’s a forty-minute drive to the medieval walled city of Siena, should you fancy a day trip, but the surrounding area has plenty to keep you busy with walking trails and wineries galore.

Outside, an immaculate lawn is fringed with herbs and wildflowers, and secluded by ancient trees. Slip into the rectangular swimming pool and float beneath the blue skies in summer, or bag a lounger and while the day away with a book in hand. A handful of terraces and balconies are home to outdoor dining areas and seating nooks with fabulous country views. 

Inside, the lounge is a vision of old-world charm with brick archways leading from one seating area to another. Pull up an armchair at the arched picture window, which frames the forest-clad hills outside like a work of art. Or, opt for a seat by the old hearth which still has its cooking pot on display. The kitchen itself is a minimalist haven of terracotta floor, wood-beamed ceiling and exposed stone where pristine white cabinets hide every appliance a piece of crockery you could need for self-catering.   

Arches & Enclaves

Hot Tub

Tucked away amid gentle hills in the picturesque Val d’Orcia, this home is perfect for large groups. The traditional Tuscan villa and its annex have been elegantly restored, blending rustic charm with modern amenities like a professional kitchen. The jasmine-, rosemary-, and lavender-filled garden features two private swimming pools and a furnished terrace with a pergola – perfect for alfresco dining – overlooking Montalcino. Siena is just a thirty-minute drive away, and you can reach the lively borgo of Buonconvento in no time. Beautiful and peaceful, this home offers a stay to remember. 

Lavender & Jasmine

Library of Books

Luxury Toiletries

Extra Pillows and Blankets

Desk / Workplace

Single-Level Home

Balcony

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

Black-Out Blinds

For a taste of authentic Italian living, this stylish home opens its doors to the beauty of southern Siena.

Located in the historic town of Montalcino (renowned for its Brunello wine), this is the perfect setting to experience the warmth and depth of Italian living. It feels traditional here with elegant styling that adds comfort and ease. From preparing your morning coffee in the kitchen to sitting in the private garden, this is the kind of space that inspires you to slow down and savour the moment. 

Follow the views of the Val d’Orcia and take a stroll through the charming streets of Montalcino, making a stop in one of the cafes or restaurants to enjoy the atmospheric beauty. Or wind your way through the rolling hills towards Siena – only a fifty–minute drive away. 

As the sun sets across the countryside, you’ll love coming home to this sanctuary in the trees. Open the doors and enjoy an evening in true Italian style – with beautiful food, wine and conversation.

Rosemary & Olive

Smart TV

Sauna

Tennis Court

This romantic castle is immersed in the natural beauty of Tuscany. Perfect for weddings, celebrations or retreats, you’ll find it easy to fall in love with the magic of this unique home. There’s a swimming pool, a private tennis court, peaceful grounds and a wellness area with a gym and sauna. Inside, the rooms offer an abundance of character as well as luxurious home comforts. Your host is on hand to help organise special extras like wine-tasting and cookery lessons. Plus, you can sample the estate wines and olive oil. You will need a car to get around, but it’s just a short drive to medieval Buonconvento. 

The Adelina 

This traditional countryside home is nestled in the hills of Siena. The grounds offer stunning views, a private swimming pool and a covered terrace with a barbecue for alfresco dining. You’ll find the rooms are set across the main house and an independent cottage – making this a great option for groups in search of space to relax independently and together. You’ll also find plenty to keep the whole family entertained with table tennis, a bocce court and a yoga area. Daily breakfast is included in you stay along with housekeeping. Plus, your host can help organise extras like massage treatments, wine-tasting and horse riding. You will need a car to get around, but it’s a short drive to the medieval village of Buonconvento.

The Wonder Garden

This restored farmhouse is situated on a family-owned estate of rolling hills, organic farmland, vineyards, and olive groves. From its hilltop position, it offers sweeping views of the surroundings and all the way to Montalcino. Buonconvento, one of the prettiest medieval villages in the region, is a short drive away, and Siena is slightly further afield. The outside space includes a private pool with sun loungers and deck chairs, as well as a bocce court and a ping-pong table. Inside, the villa blends traditional features like wooden beams with modern comforts and style. It’s an attractive home-from-home. 

A Tuscan View

Fenced Property

Outdoor Fireplace / Firepit

Located in the pretty hilltop village of Montalcino, this home is a Tuscan gem with a lot to offer. There’s a beautiful garden with a pool and a hot tub to ensure optimum relaxation. You’ll also have a traditional wood-burning pizza oven and a fire-pit for magical evenings under the stars. Inside, the rooms are just as inviting with traditional and luxurious features. The main bedroom comes with a romantic bath tub and two of the bedrooms are located in the annexes for extra privacy. Daily breakfast and housekeeping are included in your stay. Plus, it couldn’t be better placed for adventures across Tuscany. From here, it’s just a short stroll into the village centre, while Pienza, Montepulciano and Siena are all within driving distance. 

The One Light

This charming old farmhouse is between Buonconvento and Monteroni d'Arbia, southeast of Siena (25km away). It is a perfect place for a relaxing break with friends or family, made up of three beautifully restored apartments that share a private swimming pool. Each kitchen is brimming with Tuscan rusticana and has everything you need for self-catering. That’s if you’re not too busy using the stone barbecue outside and dining beneath the vine-dappled pergola. To top it all off, there are killer views of the Tuscan countryside at every turn.  

The Dream of Tuscany

DVD Player

Board Games

DVD Library

Pool / Snooker Table

Carbon Monoxide Detector

Fire Extinguisher

Smoke Detector

Nestled in the Tuscan countryside, this impressive home is the stuff that dreams are made of. It's compromised of a main house and a guest house, and is situated on a biological farm where the owners produce wine and olive oil. With nine bedrooms and numerous living areas there's plenty of space for everyone's needs. You'll love curling up with a good book on the patio, challenging your guests to a game of ping-pong, or splashing around in the swimming pool. The hosts generously allow you to take fresh produce from the vegetable patch and eggs from the hen house, and they will also provide a barbecue and pizza oven for alfresco dining. And, if you need to indulge in a little rest and relaxation, then head to the spa room – there's a sauna and whirlpool bathtub. It would be easy to spend eternity in this little patch of heaven, and we don't blame you if you don't ever want to leave. However, for those who want to get out and about during their stay, it's a forty-minute drive to beautiful Siena, where plenty of museums, restaurants and galleries await. Alternatively, there's a golf course and a riding stable nearby – your options are endless.

Gold Rush

Blender

This villa is a rural oasis just south of Siena in the peaceful countryside, surrounded by woodlands and hills with panoramic views of Montalcino and Monte Amiata. You're just 24km from the charming city, while the Tuscan coast and Florence are also just over an hour's drive away, making it the ideal destination for those wanting to explore the area. The villa provides plenty of outdoor living space, including an alfresco dining area, a shaded lounge space and a poolside deck with a private pool. Inside, a bright and spacious living area with traditional features awaits you, as well as a country-style kitchen and five welcoming bedrooms, benefitting from wood beams and exposed brick. 

The Olive House

Experience the timeless beauty of Tuscany with a stay in this historic home. Nestled in the heart of the Val d’Orcia, you’ll be treated to stunning views and a private swimming pool as well as estate grown olive oil and wine. There’s also a yoga shala and plenty of shaded spots for quiet reflection – making this the perfect setting for a retreat or refreshing family gathering. Inside, the rooms make it easy to switch off, unwind and spend quality time together. Your host can also help organise a range of extra services – including massage treatments and yoga sessions. You will need a car to get around here, but it’s just a short drive to Siena and Montepulciano.

Journey to Beauty

Netflix

Streaming Services

Baby Bath

Changing Table

Shared Pool

Gated Community

Resort Access

This hilltop haven is perfect for those looking for a quiet, calm and restful stay in Tuscany. The villa can be found thirteen minutes outside of Asciano, with its medieval centre, amid stunning rolling countryside that catches the eye from every angle. 

The villa has been restored from an elegant country house, so it retains lots of lovely Tuscan charm ¬– think heavy wood beams, terracotta accents and a classic stone facade. The layout is quirky, with two loft spaces housing the bedrooms – the plus side to all the stairs is that the views are incredible. 

The countryside that surrounds this home is lush and green, with plenty of nearby routes for hikers to get stuck into. It’s also very close to Chianti country, so you might like to seek out a vineyard tour, or at the very least pick up a bottle to enjoy on the terrace one evening. 

In terms of day trips, you can’t do better than driving thirty-five minutes to Siena. It’s a glorious city to explore, with its rich history and a wealth of fantastic restaurants. After a day out, head back to the villa for a dip in the pool in the early evening – it’s a splendid spot for a sunset swim. 


Tuscan Hills

Sound System

A true rural oasis, this flower-framed Tuscan farmhouse beautifully blends traditional charm with modern comforts to create the perfect quiet retreat. Hills teeming with olive trees, cypresses and holm oaks surround it on all sides, best enjoyed from the home's panoramic terraces. Inside, meanwhile, brick-clad archways, stone flooring and exposed beam ceilings blend with elegant furnishings in the living room to create a feeling of countryside grandeur. Wander around the garden brimming with lemon trees, jasmine and oleander plants and down the path to the secluded swimming pool where sun loungers invite luxurious afternoon relaxation. An outdoor dining table beckons at mealtimes for barbecue feasts, while the indoor pool table and the bedroom reading platform are perfect for whiling away quiet hours when the sun gets too hot. With the medieval village of Trequanda just a few minutes walk away and Siena reachable by car in just forty-five minutes, there’s plenty of exploring to enjoy in and around your private haven. 

Oleander Oasis

Games Room

Wine Cellar

Wine Cooler

Private Washing Machine

Private Dryer

Cleaning Products

Exercise Equipment

Ceiling Fans

Hammock

Safe

Bookended by the olive groves, cypress trees and rolling green hills of Southern Tuscany is this 1960s-style architectural feat designed and curated by a sculptor and architect duo. Perfect for two couples or a small group of friends looking to explore the region, this cleverly converted warehouse is airy and open-plan with large crittall-style windows looking out over the vineyard and rambling countryside beyond. We particularly liked the stone fireplace and curated pieces of art dotted around that make for a real visual statement. Through to the bedrooms, where you'll find minimalist interiors, crisp white bed linens and antique objects that combines traditional touches with modern influence. Spend mornings idly relaxing underneath the warm Tuscan sun by the stunning 20-metre lap pool or recharging in the sauna, before cycling to the nearby village of Montisi. Take a half-hour drive to the famous vineyards of Montepulciano and bring a few bottles of vino back with you – to be chilled in the home's wine cellar and enjoyed out on the terrace, as you look out across the medieval ruins of Montelifrè Castle. Be it wine, history, interior design, or art, this home delivers in spades. 

Architectural Narrative

Temperature Control

Paid Parking On Street

Buzzer / Wireless Intercom

Rooftop Terrace

Stair Gates

Sitting within a stone building dating back to the 17th century, this apartment in the hill town of Montalcino mixes Tuscan tradition with contemporary amenities to make for an address that you're unlikely to forget after a visit.

Along with the wooden ceiling beams and handsome brick flooring, you'll find comfy leather sofas, a glass dining table sat underneath an equally eye-catching chandelier and a kitchen with a wealth of surface space for whipping up something spectacular.

However, the standout feature sits just outside — step onto the home's roof terrace and guests are rewarded with the verdant Val d'Orcia, a UNESCO World Heritage Site. Up here, there's a table for alfresco feasts and a pair of loungers for soaking up the sunshine.

The local town may be small, but there are plenty of restaurants, bars and shops selling locally grown produce to keep you occupied. A little further afield, the spas of Bagno Vignoni take twenty-five minutes to reach in the car and the 9th-century Abbey of Sant'Antimo is a fifteen-minute drive.



Brother Sun

Cafetiere

Bicycles

Beach Essentials

Outdoor Bathtub

Security Cameras

​​Restored by an Italian architect with a gentle touch, this villa has been updated and split into more modern apartments, but without ever compromising on the original charm. By honouring the villa's history – and thereby retaining its character – the home feels traditionally Tuscan with its terracotta tiles and wooden beams. Walk barefoot across the floors to savour the coolness of those tiles on hot days, or light a fire in the wood-burning stove and stare up at the beams, imagining what life would’ve been like here. Nonnas rolling out pastry for tortellini, children helping churn gelato, wine flowing, and bowls of food changing hands in a celebration of ingredients, and life. You might even wish to recreate that – a holiday well spent.

Alternatively, spend lazy afternoons sitting under the vines outside as you watch the sunset on the horizon. Head out to authentic Italian pizzerias for pizza and gnocchi, or make a gelato run before exploring the surroundings. 


Bellissima Casa

Playground

Located in the heart of San Quirico d'Orcia, this apartment has romance written all over it. Inside, the Tuscan character beckons you to cosy up with your loved one after exploring the town's historic squares and local eateries. The kitchen is small but well-appointed, and though the living area lacks natural light, the private terrace more than makes up for it. Boasting views of the village church and the rolling hills in the Val d'Orcia, we can't think of a more idyllic setting to enjoy a glass of wine and a sunset meal for two.

The Maestro's Retreat

This Tuscan villa is perfect for large groups. With a main house and separate annex rented as one home, each with its own living area, kitchen/dining area, and bathrooms, you can holiday together while still enjoying your own space. While the traditional decor may not be to everyone’s tastes, we’re sure everyone will appreciate the outdoor space – with spectacular views across the Tuscan countryside, a private pool, and alfresco dining, what's not to like? Location-wise, you’re 9 kilometres from Casciano di Murlo for shops and restaurants, 6 kilometres from the natural hot springs of Terme di Petriolo where you can enjoy a soak, and 30 kilometres from historic Siena.

Charming Countryside Villa

Amazon Prime

Bathrobes

Ice Machine

Parking On Street

Wheelchair Access

Formerly an olive mill, this Tuscan villa combines rustic charm with modern design elements. Just outside the small hamlet of Iesa, the villa is nestled in the serene Tuscan hills, surrounded by verdant countryside. Downstairs you will find the original stone olive mill, alongside chestnut beams, exposed stone, and terracotta tiling across the house. This preserved charm is compounded by contemporary bathrooms, and a sunroom with floor to ceiling windows, where you can admire the oil painting of a view. On cooler nights, gather here with a drink in hand for a movie or to play some music. Outside there is a table which seats ten, for al fresco dinners before a spot of stargazing.  

No detail is spared here. From the food and drinks hamper waiting for you in the kitchen on arrival, laden with complimentary wine, olive oil, fruit and cooking supplies, to the range of activities available to book through your host, whether it be horse riding, a cooking class, or a cycling trip. There is no better area for lovers of nature and beauty. There are plenty of nearby hiking trails through untouched woodland, with panoramic vistas over the countryside. Hop in the car for fourteen minutes to reach Terme di Petriolo, famous natural hot springs set in a wooded valley. After a day of exploring, cool off in the enormous pool, before an aperitivo and a sunset barbecue. La dolce vita.

Emerald Hills

Set within the atmospheric streets of central Montepulciano, this traditional apartment sits like a gateway to the timeless beauty of Tuscany.

Overlooking the verdant garden of an ancient fortress, every detail of this home is steeped in the historic charm of its location. From the traditional features to the antique furnishings and artwork, it’s the kind of space that feels authentically Italian – inviting you to slow down and savour life’s simple pleasures. So whether you’re sipping your morning coffee on the little balcony, or preparing a light bite with local delicacies, it’s easy to feel inspired by the small details of this setting. 

Stepping outside, you’ll find it’s just a short romantic stroll to the medieval piazza, churches, viewing terraces as well as restaurants and cafés. And for explorations further afield, Montepulciano provides easy access to the majestic cities of Tuscany – both Siena and Florence are within driving distance. 

Casa Dolce Vita

Laundry Supplies

Luxury Bedding

Heated Pool

Sauna / Steam Room

Steam Room

Underfloor Heating

Valet Parking

Step-Free Access

Balcony / Patio

Fenced Pool

Herb Garden

Umbrellas

This villa captures the rustic charm of old Italy. Surrounded by 40 hectares of land boasting olive groves, vineyards, orchards, and meadows with grazing horses, it’s an idyllic escape into the Tuscan countryside. A country road leads to the UNESCO hamlet of Castiglione d'Orcia. The garden is home to a rustic outdoor cooking station, a large, shaded table, and a full outdoor lounge. There’s a touch of modernity to the private, heated pool and you’ll find a sauna hidden amid the trees. The main villa is split across two levels and is a vision of old-world Italy and there is a separate annexe with further bedrooms, a second full kitchen and an open-plan living room. 

Rusticana Retreat

Wine Cooler / Wine Cellar

Jacuzzi

Electricity Adaptors

Nestled in the heart of Montalcino, just steps from the main square and cathedral, this renovated townhouse offers an idyllic location with breathtaking views to boot. Inside, it delivers authentic charm and contemporary comforts – think high ceilings and striking timber beams alongside stylish artwork and state of the art amenities. 

From heated floors to a built-in steam bath, every detail of this home beckons you to unwind in the splendour of your surroundings. After a restful slumber in the king-sized bed, fire up the Moka pot for espressos at the breakfast bar before a morning stroll through the town. The kitchen is fully-equipped for home cooking, but no trip to Tuscany would be complete without sampling the local cuisine. Lucky for you, there's an array of family-owned cafes and eateries practically at your doorstep. 

Boasting stunning views of Montalcino's iconic towers and the verdant hills of the Val D'Orcia, we're completely in awe of this home's outdoor space. Spend time sprawled on a lounger, soaking up the sun, and at mealtimes, gather under the pergola for an alfresco feast cooked on the barbecue. If you fancy venturing further afield, take a fifty-two-minute drive to the city of Siena or, closer to home, sample the region's famed Brunello and Montalcino wine at a local winery. After busy days exploring, pour yourself a glass of the good stuff and enjoy a relaxing dip in the jacuzzi under the stars.

Honey & Fig

Pool House

A traditional Tuscan farm stay, surrounded by olive groves and truffle country, this stone villa is as practical as it is beautiful. With plenty of space for a large group to spread out, there are three living spaces, each with a kitchen, allowing for added flexibility.

Here, the name of the game is relaxation, and it's not hard to do in such a peaceful setting. In a quiet, rural area with incredible views of the lush green hills, you'll have country walks and cycling routes on your doorstep, and pretty grounds to explore – plus it's just a walk through the woods to the nearby village.

Inside, two entrances each lead to a living area and kitchen. Traditionally styled and oozing Tuscan charm, you'll have tiled floors, chestnut beams and fireplaces, along with archways and shuttered windows. Each section has a large dining table so you can all eat together and each of the five bedrooms upstairs boasts its own bathroom so nobody draws the short straw.

But we think you're likely to be spending much of your time outside. Here you'll have your own fenced pool with sun loungers and there's a little treat by way of a poolside loggia with a kitchenette and barbecue – plus a covered terrace to eat on. All surrounded by olive groves and with the old farm's well in the garden, it's a stunning natural setting.

For trips out and about, drive into Siena to see the sights, or explore the Crete Senesi and the Val d'Orcia. And if you're planning a special celebration, ask your host to arrange a private chef for a truly memorable meal.

The Well Garden

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