Castelnuovo Berardenga

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Library of Books

Board Games

Smart TV

Sound System

Entertainment

Bathtub

Bathrobes

Hair Dryer

Toiletries

Bathroom

Dishwasher

Microwave

Pod Coffee Machine

Freezer

Fridge

High Chair

Kitchen

Kitchen & Dining

Washing Machine

Dryer

Cot / Crib

Ironing Board

Drying Rack

Bedroom & Laundry

Swimming Pool

Private Pool

Outdoor Pool

Wellness & Fitness

Wi-fi

Internet & Office

Fireplace

Air Conditioning

Central Heating

Heating & Cooling

Parking Available

Private Parking

Free Parking

Parking On Street

Self Check-in / Check-out

Parking & Access

Barbeque

Patio / Terrace

Balcony

Garden

Beach / Pool Towels

Outdoor Seating

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Welcome Hamper

Nice to haves

Fire Extinguisher

First Aid Kit

Other

Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding. The interiors have preserved the grace of earlier ages while adding the essential modern cons and amenities.  Exposed wood beam ceilings, tiled floors covered with vibrant carpets, and gorgeous vintage furniture make you feel at home, yet so far away from the current era. The master bedroom comes with a four-poster bed, and overall, all sleeping quarters exude a pampering feel accentuated by the gorgeous period furniture. We love the huge dining room, the walls of which are lined with well-stocked bookshelves. After a hearty meal, grab a book, amble outside to the sundeck and lose yourself in another world. When the warmth overwhelms you, take a cooling dip in the massive pool. In the evening you can savour wine and antipasti on the veranda or under the vine-wrapped pergola. If you get the itch to explore, a thirty-minute drive will take you to Siena where you can enjoy dining, shopping and sightseeing. 

The Vine Song

DVD Player

Satellite / Cable TV

Ping Pong Table

Oven

Stove

Toaster

Coffee Maker

Kitchen Utensils

Cooking Essentials

Iron

Hangers

Laptop Friendly Workspace

Free Parking On Premises

Private Entrance

Mosquito Net

Pets Allowed

Pets

This traditional farmhouse, buried deep in the Tuscan hills, offers guests a taste of everything this area is known for – picturesque mountain views, pretty vineyards and lush olive groves. Sat in the heart of 'Chiantishire', you’re surrounded by idyllic villages like Castellina and Radda, and perfectly placed to explore this world-renowned wine region. Back at the home, you’ll find everything you need for the quintessential Tuscan trip, with a glimmering pool overlooking the rolling hills, plenty of seating areas dotted around the lush green gardens and a sun-kissed patio, plus enough space to make sure a large group can sprawl out and unwind. Set across two buildings, both interiors exude rustic charm with beamed ceilings and stone archways. Furnished with plenty of Italian passion, there are comfy sofas, a huge dining table and an authentic kitchen. Fire up the barbecue and wait for the meat to grill while indulging in a sundown aperitivo, then dine alfresco long into those balmy summer evenings.

Rolling In Olives

Sonos

Baby Bath

Luxury Toiletries

Blender

Espresso Machine

Ice Machine

Kettle

Cleaning Products

Extra Pillows and Blankets

Laundry Supplies

Vacuum Cleaner

Desk

Electricity Adaptors

Fenced Garden

Fenced Property

Herb Garden

Umbrellas

Carbon Monoxide Detector

Child Friendly

Smoke Detector

Just driving up to this fabulous Tuscan home is a pleasure in itself. Surrounded by manicured lawns, tall cypress trees and rolling hills, it's an imposing place in a secluded setting. Within the private estate of Arceno, it comprises a main stone-built villa and an Annesso – a historic barn converted into a separate intimate home. The main house is dominated by its central courtyard, while the lush gardens are home to a stunning pool and outdoor dining spots. We love the thought of gathering the whole gang around the long dining tables for lazy lunches of lemon ravioli and chilled white wine, lasting far into the afternoon. Inside, this home is elegant and comfortable, with period features, antique furniture and grand reception rooms. The concierge service makes things even easier, providing items ranging from the basic (oil and selected toiletries) to the delectable (spirits and house wine). One of the best ways to acquaint yourself with the landscape is to book a horse riding session, but if that doesn’t appeal, a walk out into the countryside is just as charming. For the more energetic among us, day trips to Florence and the region’s major towns are possible. 

Botticelli's Primavera

Netflix

Streaming Services

Changing Table

Shared Pool

Desk / Workplace

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

DVD Library

Black-Out Blinds

Exercise Equipment

Stair Gates

Nestled among the lush greenery of an expansive 1,000-acre private estate, this beautifully restored stone villa is ideally located to allow you to enjoy the ultimate holiday with your family or a group of close friends. Picture yourself serenely floating in the infinity pool while taking in the view of the rolling Tuscan hills below. Imagine sipping a medium-bodied Chianti and tucking into fresh pasta on the sun-drenched terrace while waiting for the Instagram-worthy sunset. There are a couple of barbecues, so you can always indulge in plenty of Florentine steaks if you get weary of pizza and pasta (is that even possible?). When you've had your fill of sumptuous Italian fare, play your favourite tunes on the Bose sound system and chill out with some board games by the fireplace. If you feel like you might have over-indulged, fear not. You can keep up your workout regime by sweating it out in the fitness room or hiking through the surrounding countryside. The medieval village of San Gusmè is a mere five-minute drive away, while Siena is a 30-minute trip from your villa, in case you want to do some shopping or sightseeing. Your host provides a complimentary concierge service, too, so that all your holiday whims will be taken care of. Before long, you'll feel like a local.

Chianti Kisses

Juicer

Immersed in the natural serenity of the Chianti countryside, this home sets the tone for an idyllic Italian escape. From its hillside position, you can enjoy incredible views across the valley. There’s a saltwater swimming pool for refreshing swims, a peaceful garden and a covered terrace with a barbecue for alfresco dining. Inside, you’ll be welcomed by a rich sense of history, charm and plenty of character. Your host is on hand to help organise a range of sweet extras – including grocery deliveries, private chefs and organised excursions. Plus, it’s possible to drive to Siena and Arezzo, while the nearest amenities are in San Gusmè – just 4 kilometres away. 

Tuscan Flower

Jacuzzi

Hot Tub

Amidst the rolling hills and long stretches of vineyards, you'll be captivated by the peace and serenity of this place from the moment you arrive. Stone clad brickwork and cobbled paths set the scene with a backdrop of the surrounding countryside – painting a picture-perfect view of blissful Tuscan serenity. Inside exposed wooden beams and traditional tiled flooring bring charm to the otherwise modern interiors, and you'll have the choice of eating alfresco or at cooler temperatures from the indoor dining area, when it comes to meal times. Take a dip in the outdoor shared pool, or embark on the day's adventures in and around Tuscany. With golfing, horseback riding, cycle paths and walking trails on offer, if you're the. outdoorsy type – this is the place for you. After a day of exploring feel rest assured in knowing that the bubbling jacuzzi awaits your return – but don't forget to pour yourself a glass of wine before getting in. 

Tuscan Serenity

Located amidst the rolling hills and vineyards of Chianti, this Tuscan oasis makes for a serene retreat. There is plenty of space inside for the whole brood to spread out, thanks to an array of lounges and cosy bedrooms. Sure, the design is traditional, but extras like the welcome hamper and bottle of local wine make it easy to settle in. Out in the landscaped garden, you can splash in the private pool or find a spot to enjoy an alfresco aperitif. Your host can also arrange top-notch services to elevate your stay, from daily housekeeping to guided tours and cooking lessons.

Tuscan Roses

Heated Towel Rail

Rain Shower

If this characterful apartment set in an intimate agritourism complex doesn't say Tuscany, we don't know what else will. Surrounded by hectares of olive groves, the home's secluded setting is idyllic. But you're never far from the bustle, with the wander-worthy streets of Siena and countless medieval walled towns all just a short drive away. Inside, the traditional interiors are perfectly in tune with the heritage of this 15th-century farmhouse estate comprised of just five charming apartments. While the indoor living space is limited, the sheltered private terrace and Jacuzzi (for an additional fee) with views of the Tuscan hills are a delight. And wait until you see the shared swimming pool and vast communal lawns at the heart of it all.

Tuscan Hideaway

Garden Games

This villa strikes the perfect balance between contemporary and traditional. The terracotta ceilings and floors are original features, but the kitchen and lounge on each level are totally modern – not to mention convenient for larger groups. But it's the sprawling garden that captured our attention. A private swimming pool is a lovely addition during the summer, a separate outbuilding has table tennis and darts, and several seating areas offer spots to relax with a glass of wine – our favourite being the courtyard, ideal for alfresco dining. The nearest village is San Gusmè, but most shops and eateries are in Castelnuovo Berardenga (6 kilometres away). For day trips, head to Siena – just thirty-five minutes by car.

Siena Ceremony

Bicycles

Sauna

Outdoor Shower

This is an excellent base from which to explore Tuscany and Chianti. The stone villa is a classic example of Tuscan style, which has been renovated into a comfortable home – it has everything you might need and is still full of authentic charm. 

You’ll wake up under an authentic wood-beamed ceiling in one of the elegant bedrooms. Making your way downstairs, past antique paintings and a grandfather clock, you’ll enter the dining and living space. As in any Italian home, this is the heart – you’ll likely spend hours sitting around the dining table.

Outside, the covered veranda is the perfect place to sip coffee – or vino in the afternoon. The pool is a short stroll away, surrounded by lush lawns and trees. It’s a dreamy place to be whether you’re swimming laps, soaking up the sun by the water, or reading a book in the Jacuzzi. 

The villa is a twenty-nine-minute drive from Siena, which is a great city for day trips. Discover the history of the Palio, enjoy a spot of shopping, and treat yourselves to a decadent lunch in a piazza. 


Sipping Chianti

Nestled between Siena and Arezzo, this villa ticks all of our boxes for a memorable stay in the heart of Tuscany. The abode is made up of a main house and a separate residence with a living area, kitchenette and en-suite bedroom (ideal for those who like their privacy), so there’s plenty of space for the group to spread out. Not only are there luxury additions like a sauna, pizza oven and swimming pool, but your host also provides a complimentary wine experience and dinner on your first night to make your time here that extra bit special.

Treasure in Tuscany

Cafetiere

Courtyard

Surrounded by vineyards and olive groves, this charming stone villa welcomes families to explore Chianti. Drive to the lively market town of Gaiole and Brolio Castle, or admire the Tuscan countryside of Castellina in Chianti. The home itself features ample outdoor seating. Everything from the poolside sun loungers to a shaded alfresco dining table gives you the space to unwind. The swimming pool will go over well with the entire family, and the sprawling garden is a treat for little ones. With one bedroom found in the annexe, it also gives a couple, teenagers or grandparent a little more privacy.

The Chianti Essence

Tucked away on the edge of San Regolo village, this is a perfect pad for two couples or a small family on an Italian stay. Sure, its traditional interiors may not be to everyone’s taste, but the outdoor space will be a popular spot with all. The private terrace is just the place for an alfresco family meal, while the communal pool promises some respite from the heat. Locally, we recommend a trip to Brolio Castle. This charming estate serves up a wine-tasting room, castle, and restaurant serving authentic Tuscan food – there’s something for everyone here. 

The Tuscan Hills

Escape to the Tuscan countryside and experience the charm of this beautiful home, a lovingly restored 19th-century barn perched atop a hill. Surrounded by breathtaking views of the valley, Monte Amiata, and Monte Cetona, this eco-friendly retreat promises a tranquil haven for couples or families seeking a break from the hustle and bustle of daily life. Sure, at full occupancy, two people will sleep on the sofa bed in the living area, but it’s no hardship in this chic, contemporary home. Location-wise, you can hike, bike, visit mediaeval castles or take wine tours – there’s something for everyone here. 

The Charm of Tuscany

You could never tire of the rolling hill vistas seen from the private terrace of this pet-friendly Chianti apartment. Set in a handsome farmhouse dating to the 15th century, the home has been reimagined into five independent apartments with a shared swimming pool surrounded by hectares of olive groves at its heart. Inside, while the traditional interiors are charming, the living space with one sofa may feel tight if four of you are sharing. But with a private sun-kissed veranda and Jacuzzi (for an additional fee) outside, we don’t think you’ll mind. Location-wise, take your pick from medieval walled towns or wander-worthy Siena – it’s all just a short journey away.

Olive Green

Wine Cellar

Pool House

Outdoor Fireplace / Firepit

Sitting proudly in the Chianti landscape, surrounded by woods, olive trees and row upon row of vines – this ancient farmhouse is the dream. It’s located in the prestigious setting of the Tolaini organic winery, one of the most esteemed in the area and produces delicious extra virgin olive oil and a fine selection of wines exported worldwide. You can taste a selection of these wines in the estate’s cellars a short distance away.

That’s if you can tear yourself away from the gorgeous gardens with their fragrant lemon trees, lavender and rosemary bushes. Fire up the wood oven or barbecue, then dine alfresco under the pergola covered in exquisitely scented jasmine. After lunch, take a dip in the swimming pool with its vistas over the stunning countryside. 

Inside, a renovation has maintained the charm and character features such as the brick arches and vaulted ceilings. We love the huge dining table, which follows the curved lines of the kitchen – it’s perfect for entertaining your family and friends. Upstairs, the bedrooms have glorious countryside vistas, four posters and beds with beautiful landscapes painted on them. The master has a whirlpool tub, too, if you want to have a luxurious soak.

If you fancy exploring the area – Siena is a twenty-minute drive away with its splendid Palazzo Pubblico and Torre del Mangia, a slender 14th-century tower. 


Beneath The Autumnal Sun

Shared Washing Machine

Balcony / Patio

Safe

With stunning views of the valley, this ground-floor apartment in this countryside resort has its own outdoor dining area where you may spot passing deer and other animals. There’s a shared swimming pool, a short stroll away too (though there are numerous wooden steps down to it). Inside this home, the décor is quite traditional and simple, but with so much on offer in the area, will you actually spend much time indoors? The resort boasts 10 kilometres of marked trails for hiking through the woods and vineyards of Fietri, while the pretty towns of Castelnuovo Beredenga and Gaiole are both 15km away via winding roads. 

The Chianti Garden

Tennis Court

This rustic villa caught our eye for its remote location and peaceful countryside surroundings (best enjoyed off the secret terrace accessed from the fifth bedroom). The nearest town of Ambra lies 10km away, so car hire is essential – though there'll be no interruptions here. You'll find plenty of tranquil outside spaces from which to soak up the glorious setting – from the swimming pool, garden and dining area to the tennis court, bocce court and table tennis space (you've also got a well-equipped gym). And, while the traditional interiors might not be to everyone's taste, keen chefs will love the modern kitchen, which makes alfresco cooking a delight. 

The Daisy Cutter

Lift Access

Amidst the rolling hills and vineyards of Chianti, this home is perfectly positioned for an idyllic Italian escape. Set within a private estate which includes a vineyard, olive groves and a church, you’ll find everything you could need for a relaxing retreat or special celebration. There’s also a private pool, a gym and an independent barn for two guests – ideal for those seeking a little extra privacy. Daily housekeeping can be organised along with a range of extra services such as a private chef and guided tours. You will need a car to get around here, but it’s just a short drive to the nearest amenities in Castagnoli and San Gusme.

The Sunlight Hideaway

Fenced Pool

Part of a 13th-century estate-turned-resort, this apartment makes the most of its scenic location in Chianti. Alongside a private terrace, you'll have access to a communal hilltop swimming pool, shared laundry room, and walking trails through the nearby vineyards. The design is definitely traditional, but we're fond of the rustic character – in fact, anything more contemporary would feel out of place in this storybook setting. Speaking of location, pack comfortable shoes. Not only is the apartment set over two levels, but the hilly environment means you'll do lots of climbing. A car is also a must since villages like Gaiole, Radda, and Castelnuovo Beredenga are within driving distance.

Vino on the Terrace

Parking On Premises

Nestled in the heart of the Tuscan countryside, this charming cottage offers a tranquil retreat for families or small groups. Set on a resort, if you’re not enjoying the privacy of the cottage garden or hot tub, you can take a refreshing dip in the shared pool, just a short stroll away, or challenge your friends to a game on the tennis court. With walking trails including the Dievole Natural Path on your doorstep, wine tasting, and nearby villages to explore, you’ll find the perfect blend of relaxation and adventure.

Tuscan Flow

Perched upon a private hilltop in the Chianti hills, the setting of this villa estate is hard to beat. Designed to make the most of those next-level views from all angles, the home has a private pool area and an alfresco dining terrace to soak in the vistas, and inside, a second-floor lounge with far-reaching panoramas. You're in good company here with a castle estate just 2.5km away offering tours, wine tasting and fine dining. Beyond that, the Chianti towns of Gaiole (8.5km) and Castelnuovo Berardenga (11.5km) are an afternoon well spent. Or plan a day trip to Siena, a scenic 20km drive away.

Chianti Hills

This studio apartment in a stone barn conversion is a perfect blend of modern and antique design. We love the infinity pool (40 metres away) which overlooks the Val d'Orcia, offering breathtaking views. It’s surrounded by wild plants and shrubs that reflect the forested land beyond. The owner’s live in the main house with their two friendly dogs and they occasionally use the pool when the area is unattended by guests. The private furnished terrace and outdoor lounge area here is a lovely spot for a glass of wine. If you prefer to be a bit more active, there are endless trails and routes for walkers and bikers, while the pretty village of Gaiole is 11 kilometres away.

The Chianti Cottage

EV Charger

Nestled amidst vineyards and olive groves, this villa offers an unforgettable retreat in the heart of Chianti Classico. Set on a winery, it’s no surprise that there are plenty of outdoor spots just made for sipping a glass of wine at the end of a busy day. Add in a private pool and far-reaching countryside views, and this home ticks a lot of our holiday boxes. Ideal for larger groups, we also love how this home flows over three separate buildings, with the cottage and annexe alongside the main villa – perfect for those wanting to holiday together, yet still enjoy some privacy. 

Chianti Glow

Nestled in a private estate overlooking the Chianti hills, this cottage sets the tone for a magical Italian stay. There’s a private terrace and outdoor seating for alfresco dining, while the rooms make it easy to switch off and unwind. You can enjoy access to the shared swimming pool and there are plenty of spots where you can sit back and admire the views. It also makes a great base for exploring this beautiful region. From here, its a short drive to the local villages of Lecchi and San Sano, while Siena and Florence are also within driving distance. 

Chianti Sunrise

Nestled on a hillside in Chianti with far-reaching views, this ground-floor apartment is part of a small resort. While it does lack natural light in some areas due to its history as a farm building, it’s comfortable and well-equipped for a restful retreat. With two private terraces, you can soak up the Tuscan sun or enjoy some shade, while the communal pool offers the perfect place to cool off – just don’t forget to take in the view. Keen to explore? Hike the Dievole Natural Path from your doorstep, with all trails leading to a wine-tasting cellar and an open terraced restaurant.

Tuscan Delight

Set in hectare upon hectare of olive groves and yet just a short drive from the wander-worthy streets of Siena and countless medieval walled towns, the setting of this Tuscan farmhouse apartment is postcard-perfect. A wonderful retreat for two, a single traveller, or a small family, you'll have a private terrace with a barbecue and Jacuzzi (for an additional fee) to soak up the rolling hill vistas, and just across the communal lawns, a shared swimming pool to beat the Tuscan heat. While the traditional interiors might not be everyone's cup of tea, the historic features of this 15th-century estate are impressive.

A Visit from Siena

Children's Dinnerware

Private Washing Machine

Private Dryer

Luxury Bedding

Heated Pool

Multiple Sets of Keys

Outdoor Audio

Pet Bowls

Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shady stroll, and vineyards tumble down the hillside around you. Set up for a lazy lunch beneath the pergola – there’s dining for the whole group here. Shared between a handful of stone villas on the same estate, there’s a swimming pool at the bottom of the garden.

Inside, whitewashed wooden ceilings speak of days gone by and there’s a traditional Tuscan farmhouse vibe throughout. Terracotta floors keep things cool underfoot and bedrooms and bathrooms are all super spacious. The kitchen in jolly aquamarine-blue is more than big enough to handle the hustle and bustle of a busy breakfast time too.

Exploring the area, you’ll find the charming village of Lecchi to be a six-minute drive away where the ruins of an ancient castle await. Plus you’re in the Chianti wine region where the hills are dotted with family-run vineyards and wineries galore. 

The Olive Stone

Foosball / Table Football

Games Room

Pool / Snooker Table

Surrounded by olive and cypress trees, this home perfectly embodies the timeless charm of Tuscan living. Dating back to the 15th-century, it began its life as a monastery, transitioned into a farm and now exists as the ideal setting for an immersive Italian escape. Inside, you’ll be welcomed by a wonderful sense of character along with plenty of space to stretch out and enjoy quality time together. There is also a games room, a fitness room and a wine cellar. Outside, you can stroll through the gardens, relax by the private pool and enjoy games of tennis on the private court. You will need a car to get around here, but it’s just 10 kilometres to Siena, while Florence and Arezzo are also within driving distance. 

Land of Beauty

Step into a piece of history here – once the dwelling of wandering priests a millennium ago, now transformed into holiday homes. Each villa boasts its own terrace, inviting you to savour alfresco meals and unwind with a glass of Chianti overlooking the Tuscan hills. Start your day with a friendly tennis match on the communal courts, and unwind poolside post-match. With no air-conditioning, it may feel a little warm during the summer months, but there are plenty of shaded spots when you need respite. Embark on cultural escapades to Siena, or hike the Dievole Natural Path, winding up at a winery, where you can enjoy a tasting at the cellar's restaurant.

Tuscany Magic

This traditional Tuscan farmhouse is nestled in the hills of Chianti. From here, you can enjoy beautiful views across vineyards, long days by the private pool and rejuvenating soaks in the hot tub. There’s also a terrace, a barbecue and a pizza oven for blissful Italian meals. Inside, the rooms offer a simple and peaceful sanctuary for families and groups looking to stretch out and socialise. You’ll find one of the bedrooms is located in an independent annexe – perfect for those seeking a little extra privacy. And when it comes to explorations further afield, it’s a short drive to the nearest amenities as well as Siena and Arezzo. 

Sunlight Symphony

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