Volpaia

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Satellite / Cable TV

DVD Player

Sound System

Entertainment

Bathtub

Hair Dryer

Heated Towel Rail

Rain Shower

Toiletries

Bathroom

Coffee Maker

Cooking Essentials

Dishwasher

Freezer

Fridge

High Chair

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Pod Coffee Machine

Stove

Toaster

Kitchen & Dining

Cot / Crib

Drying Rack

Hangers

Iron

Ironing Board

Washing Machine

Bedroom & Laundry

Outdoor Pool

Private Pool

Swimming Pool

Wellness & Fitness

Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Fireplace

Heating & Cooling

Free Parking On Premises

Parking Available

Private Entrance

Parking & Access

Balcony

Barbeque

Beach / Pool Towels

Courtyard

Garden

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Mosquito Net

Nice to haves

Pets Allowed

Pets

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

Cafetiere

Private Parking

Balcony / Patio

Child Friendly

Safe

Other

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

Blender

Jacuzzi

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

Dryer

Fenced Property

Nestled in the Tuscan countryside with a private pool, serene outdoor space and views across Chianti’s vineyard-laced hills – what’s not to love about this home? Comfortable for a family or group of friends, inside, you’ll find a seamless blend of traditional and modern. And, when you fancy a spot of sightseeing or some authentic Italian cuisine, you can walk to the hilltop town of Radda, just two minutes away, or for jaunts further afield, hop in the car for a day trip to Florence or Siena. 

Vineyard Sunset

Ping Pong Table

Traditional and romantic, this charming Tuscan home is in wine country, and we can practically smell the freshly uncorked Chianti from here. Beautiful to look at, both inside and out, and surrounded by lovely gardens, this is the kind of place where everything can just slow right down. Stroll to the pool for a morning swim, laze in the hammock in the shade of the trees, and casually put together delightful meals using the finest local ingredients. Inside, there are tiled floors, shuttered windows and exposed timbers, making for a rustic feel. There's a country kitchen for dining inside, but we're guessing you'll make the most of the covered terrace and eat alfresco each and every day. There’s nothing better than a wine tasting experience in these parts, so we recommend you sample the product at the Castello di Albola winery, just a ten-minute drive away. And if you're tempted to head off for a cultural day out, the stunning Renaissance city of Siena is just fifty minutes away. 

Vino Classico

Playground

Wine Cooler

Heated Pool

Parking On Premises

EV Charger

Lift Access

Breakfast Included

Alarm System

Fire Extinguisher

First Aid Kit

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

Ceiling Fans

Outdoor Shower

With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining. Inside, the rooms are set across two floors and offer plenty of character along with home comforts. You might never want to leave this hilltop sanctuary, but it’s just 2 kilometres to Radda in Chianti where you’ll find shops, restaurants and bars. It’s also possible to drive to Siena and San Gimignano. 


The Hilltop Dream

Nestled in the heart of the Chianti region, this charming cottage seamlessly blends traditional and modern styles. Surrounded by vineyards, olive groves, and oak forests, with views of the valley and distant castles, you can’t fail to relax here. And while we love the interiors, the outdoor space just about steals the top spot. There's so much to enjoy with a private pool, sun-kissed terraces, and multiple alfresco dining areas. Keen to explore the area? You’re within easy reach of Radda, Gaiole, Siena and Florence here.  

Vines & Vistas

Pool / Snooker Table

Ice Machine

Exercise Equipment

Sauna

Smoke Detector

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

Library of Books

Bread Maker

Black-Out Blinds

Cleaning Products

Extra Pillows and Blankets

Hot Tub

Welcome Hamper

Carbon Monoxide Detector

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

Smart TV

Home Cinema Setup

Indoor Pool

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

Free Parking

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

Shared Pool

Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine. It's also got plenty of character inside – think arched doorways, terracotta floors, and beamed ceilings. Location-wise, you're just a quick car ride from Radda and Gaiole. Whether you're keen to visit the local wineries or venture further afield to Siena or Florence, this is a prime spot to explore the Chianti countryside.

Hillside Harvest

Desk

Multiple Sets of Keys

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

Board Games

Children's Dinnerware

Espresso Machine

Bicycles

Tennis Court

Workplace

Self Check-in / Check-out

Fenced Garden

Hammock

Outdoor Fireplace / Firepit

Umbrellas

Treat yourself to a relaxing stay at this rustic villa in the heart of Chianti, one of the Old World’s best known wine regions. Fully renovated in 2016, this authentic Italian home will delight even the most discerning guest with its characterful design features – think wooden ceilings and gargantuan stone fireplaces – and comprehensive selection of modern amenities. 

There’s no shortage of activities to keep you busy here – whether it’s relaxing by the pool, playing board games by the fire, or perfecting your forehand on the private tennis court – but we wouldn’t blame you if all you wanted to do was sit back and take in the view. Settle into one of the chairs in the garden and gaze out at the Tuscan hills while your private chef gets to work in the kitchen. When you’re ready to eat, gather everyone round whichever dining table takes your fancy – there are plenty of options here – and enjoy a leisurely lunch under the midday sun before heading out on a gentle hike through the gorgeous countryside. If you want to explore further afield, hop in the car and set off for Radda in Chianti where you’ll find a whole host of authentic Italian eateries, or make your way to Siena – just over half an hour away – and spend the day learning more about the region’s rich history. Back at the villa, your comfy, air-conditioned bedroom awaits, so why not head up and get some much-needed shuteye? We promise this dreamy Tuscan abode isn’t going anywhere. 

Sunflowers & Sangiovese

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

Sit back, relax and soak up the sunshine at this characterful villa in Chianti. It may be a little dated inside, but the twin apartment layout is perfect for families and groups that want their own space. Besides, the garden speaks for itself. Surrounded by vineyards and olive groves, you'll be treated to fantastic views day or night. There's a private pool, a hot tub, and a sauna for ultimate relaxation, while the terrace makes the perfect spot to enjoy an Italian feast. Paths lead down to freshwater springs with natural pools, but if you want to venture out, you'll find Radda in Chianti, Siena, and Florence all within easy driving distance.

Eternal Etruscan

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

Breathtaking views, a private pool and an abundance of charm – this home welcomes you to enjoy it all from its privileged spot in Chianti. Outside, you’ll find everything you could need to sit back and savour the beauty of this special location. There’s a terrace for alfresco dining and a little playground for children. Inside, the wine cellar offers the perfect spot for wine tastings, while the steam room and gym cover all your wellness needs. Plus, a welcome dinner is provided, housekeeping is included and a private chef can be arranged on request. It’s also just a short drive to Radda in Chianti, while Sienna and Florence are also within easy reach.  

Tuscan Bloom

Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool. While this villa welcomes dogs and allows for pampering with special services, there's no air conditioning. Plus, getting in and out of here is a bit tricky, as it calls for a confident driver to put road trips on the cards.

The Olive Vine

Foosball / Table Football

Bathrobes

Luxury Toiletries

Private Washing Machine

Private Dryer

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Access to Gym / Spa

Electricity Adaptors

Free Parking On Street

Fenced Pool

Herb Garden

Outdoor Audio

Pet Basket

Pet Bowls

Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest. 

Enjoy poolside sunbathing on plush sun loungers, before taking a dip in the cool, refreshing waters. Mornings are the perfect time to cuddle up on the veranda with a mug of something warm, looking out over rolling hills and lush vistas as the sun begins to warm your day. When the day is just too good to be spent at home, take a walk through the Tuscan countryside, before heading to Radda to sample some of the most refreshing wine and cuisine Chianti has to offer.

Citrus Pavillion

Tailor-made for two, this charming villa promises a tranquil escape in the Tuscan countryside. We love the character-packed interiors, where you’ll find everything needed to kick back and relax. But for us, the outdoor space is the real winner. Soak up the valley views, peppered with vineyards and olive groves, as you cool off in the private pool or dine alfresco under the warmth of the sun. When you’re ready to explore, you’re conveniently located between Radda and Lecchi. Personally, we’d head to Radda first to sample a bottle of its Chianti Classico. 

Sweet Tuscany

While this home is charming inside and filled with everything you need for a comfortable stay, the outdoor space is the cherry on the cake for us. Made for soaking up the Mediterranean climate, you’ll find secret pockets of garden here, so you can socialise or spend a little quiet time by yourself. The private pool offers some respite from the heat, or sun-seekers may prefer to enjoy the rays from the terrace. Keen to explore the local area? Hop on the bikes, don your helmets, and let two wheels take you away.

Tuscany Finca

This beautiful, traditional villa sits in the Chianti countryside between the wine towns of Radda and Gaiole in Chianti. It’s a splendid spot, whether you plan on exploring the local vineyards or just want to laze beside the private pool and admire the view – you can look forward to a 180-degree panorama of the countryside and a nearby hilltop town. The villa is charming and cosy, with authentic terracotta tiles and beamed ceilings. The terrace is perfect for alfresco dining. 


Chianti Hilltop

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

We immediately fell in love with the view from the swimming pool at this villa tucked into the Chianti hills. Nothing but green hills as far as the eye can see. The grounds are kept blissfully private as a long tree-lined driveway separates the house from the road, so you can dine alfresco and sip a glass of red as the sunsets in complete seclusion. The villa is a picture of Tuscan tradition, from the stone facade and wooden shutters to the original fireplaces and antique furniture inside. Step across the threshold and you’re greeted with the cooling touch of tiled floors and the rustic ambience of timber-beamed ceilings. Our favourite spot has to be the dining room when a long table stands beside the hearth, still adorned with pots and pans as if frozen in the 19th century. The breakfasting kitchen has everything you need for modern-day cooking and there’s a choice between relaxing in the grand lounge by the fireside, or in the cosy family snug. You’re in the heart of Chianti countryside here with wineries and farm-to-table restaurants dotting the hills. It’s also a forty-five-minute drive to Siena, perfect for a day trip.   

By The Hearthside

This Tuscan home is a bit special. It’s situated in the medieval hamlet of Vertine, close to the market towns of Gaiole in Chianti – just 2 kilometres away – and Radda, which is 7 kilometres away. The richness of the area’s history is reflected in the home’s decor, which includes frescoes, wooden beams, and antique furniture. Outside, you can admire views of the hamlet’s main square, as well as vistas of the rolling Chianti hills. The private pool has hydrotherapy jets, so you can unwind as you take in the marvellous views. We also love the covered terrace, which is a great spot for dining alfresco. 

Chianti Beauty

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

Overlooking the Chianti hills, this home is the ideal setting for a restorative Tuscan getaway. Spread across two floors (connected by external stairs), there are two kitchens, family-friendly rooms and plenty of space for groups to stretch out and enjoy quality time together. Outside, you’ll find the swimming pool takes centre stage, while the hot tub provides the perfect spot to sit back and admire the views. You will need a car to get around here, but it’s just a 7 kilometre drive to the nearest amenities in Radda. 

A Guide to the Hills

At this rustic villa, rolling vineyards are on your doorstep. We mean that quite literally – the owners are local winemakers, and they offer tastings in the medieval tower-turned-wine bar. They'll also arrange welcome dinners, cooking classes, private chefs, continental breakfasts, and other special touches during your stay. As for the home itself, we think it's pretty spectacular. A private pool, sun-kissed garden, and Chianti views await outside, while the somewhat traditional interior has a few surprises in store – namely, a chef's kitchen, a small gym and a wellness centre boasting a Turkish bath and steamy sauna. Location-wise, Radda is less than 2 kilometres away, and Florence and Siena are great options for day trips.

Chianti Sangria

DVD Library

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

Gated Community

Single-Level Home

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


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