Montalcino

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Library of Books

Entertainment

Bathtub

Hair Dryer

Luxury Toiletries

Toiletries

Bathroom

Cooking Essentials

Dishwasher

Espresso Machine

Freezer

Fridge

Kitchen

Kitchen Utensils

Oven

Pod Coffee Machine

Stove

Kitchen & Dining

Drying Rack

Extra Pillows and Blankets

Hangers

Iron

Ironing Board

Washing Machine

Bedroom & Laundry

Desk / Workplace

Laptop Friendly Workspace

Wi-fi

Internet & Office

Central Heating

Heating & Cooling

Free Parking On Street

Free Parking On Premises

Parking Available

Private Entrance

Single-Level Home

Parking & Access

Courtyard

Garden

Balcony

Outdoor

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

Smart TV

High Chair

Cot / Crib

Private Pool

Hot Tub

Swimming Pool

Wellness & Fitness

Air Conditioning

Fireplace

Self Check-in / Check-out

Barbeque

Fenced Property

Outdoor Fireplace / Firepit

Patio / Terrace

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

Coffee Maker

Black-Out Blinds

Outdoor Seating

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

Satellite / Cable TV

Sound System

Changing Table

Baby Bath

Kettle

Microwave

Toaster

Cleaning Products

Temperature Control

Paid Parking On Street

Buzzer / Wireless Intercom

Rooftop Terrace

Sun Loungers / Beach Chairs

Welcome Hamper

Mosquito Net

Nice to haves

Stair Gates

Fire Extinguisher

First Aid Kit

Other

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

Streaming Services

Bathrobes

Rain Shower

Blender

Cafetiere

Ice Machine

Wine Cooler

Wine Cooler / Wine Cellar

Dryer

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Exercise Equipment

Jacuzzi

Steam Room

Electricity Adaptors

Underfloor Heating

Valet Parking

Fenced Garden

Outdoor Bathtub

Umbrellas

Pets Allowed

Pets

Carbon Monoxide Detector

Smoke Detector

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

Ping Pong Table

Child Friendly

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

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

Free Parking

Beach / Pool Towels

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

Outdoor Shower

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

Outdoor Pool

Garden Games

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

Board Games

Heated Towel Rail

Heated Pool

Sauna

Sauna / Steam Room

Desk

Step-Free Access

Balcony / Patio

Beach Essentials

Fenced Pool

Hammock

Herb Garden

Sun Umbrellas

Resort Access

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

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

Games Room

Workplace

Wheelchair Access

Meeting / Conference Rooms

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

Playground

Private Washing Machine

Ceiling Fans

EV Charger

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

Outdoor Kitchen

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

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

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

DVD Player

DVD Library

Pool / Snooker Table

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

Private Parking

Nestled in the Tuscan countryside, this villa is a place for a family or group of friends to spend quality time together in the sunshine. From the hanging chair to sun loungers, the outside space offers ample opportunities to enjoy the views. Plus, there’s a covered terrace for alfresco dining. The sleeping quarters are on the lower ground floor with direct access to the garden and pool (something to keep in mind if you’re staying with young children), and the main bedroom has an open-concept en-suite, which may not be to everyone’s taste. If you fancy a change of scenery, the town of Castel del Piano is a short drive away.

The Italian Rose

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 

Safe

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 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

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

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

With its rich peach-coloured frontage, stone walls, and terracotta tiled roof, from the outside, this home looks like a traditionally Tuscan place to stay. But you only need to head down to the elegant pool to realise it has all the modern comforts you’d want, with stylish sun loungers and day beds, outdoor sofas and chic hammocks to swing in. That’s not to say it doesn’t also have Tuscan charm, as you’ll find this aplenty when sitting under the pergola enjoying an alfresco meal. And inside, you’ll discover exposed wooden beams, a brick fireplace and enchanting archways. Cooking at home is a delight thanks to the outdoor kitchen, complete with hobs and a barbecue grill. You’ll also be able to explore 2,500 square metres of planted gardens, terraces and olive trees. At night, as the lights of the pool illuminate, relax on the terrace with a glass of local wine. 

Bria

In the heart of the Val d'Orcia, this villa offers sweeping views as far as the eye can see. Montepulciano, San Quirico d'Orcia, and Seina further afield are all within driving distance – and all make great options for days out and about in the countryside. But even better than the location is the garden waiting for you back home. There's an ivy-covered pergola ideal for alfresco dining, a private pool overlooking the vineyards, and swings to keep little ones entertained. Inside, modern comforts blend with traditional character. Every bedroom has an en-suite bathroom, making this ideal for families or friends.

Sunflower Sunset

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

Immerse yourself in the heart of Tuscany with this charming villa, nestled along the historic Via Francigena. Beautifully restored, this home seamlessly blends traditional Tuscan features with modern comforts. And, thanks to its interconnecting apartments and plethora of outdoor space, it’s ideal for extended families or groups of friends, offering ample room for everyone. Dive into the refreshing pool, overlooking the Val d'Orcia hills, and savour delicious meals under the shaded pergola. If you can tear yourself away, an eighteen-minute drive takes you to San Quirico d'Orcia, where a selection of Italian eateries awaits. 

Tuscan Ornate

Wine Cellar

Private Dryer

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. 

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