Volpaia

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Sound System

Entertainment

Bathtub

Hair Dryer

Rain Shower

Bathroom

Cafetiere

Coffee Maker

Dishwasher

Fridge

High Chair

Kitchen

Kitchen Utensils

Microwave

Oven

Pod Coffee Machine

Stove

Toaster

Freezer

Kitchen & Dining

Cot / Crib

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

Private Parking

Parking Available

Private Entrance

Parking & Access

Balcony / Patio

Barbeque

Beach / Pool Towels

Garden

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Mosquito Net

Nice to haves

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

Satellite / Cable TV

DVD Player

Heated Towel Rail

Toiletries

Cooking Essentials

Kettle

Drying Rack

Hangers

Iron

Ironing Board

Balcony

Courtyard

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

Ping Pong Table

Playground

Pool / Snooker Table

Blender

Ice Machine

Heated Pool

Exercise Equipment

Sauna

EV Charger

Lift Access

Alarm System

Fire Extinguisher

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

Single-Level Home

This charming stone house is nestled in the Chianti countryside, perfect for wine lovers and those who enjoy a slower pace of life. Long, alfresco meals will be routine here, with a dining table and barbecue under the shaded pergola. The private pool is the perfect spot for relaxing on the sunlounger or taking a dip with countryside views and the location is ideal for exploring the region. The medieval village of Volpaia – and its handful of authentic restaurants – and the town of Radda in Chianti just a short drive away.

Rose Garden

Wine Cooler

Dryer

Parking On Premises

Fenced Property

Breakfast Included

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

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

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

Shared Pool

Free Parking

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

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

Chianti Hillside

Library of Books

Bread Maker

Black-Out Blinds

Cleaning Products

Extra Pillows and Blankets

Hot Tub

Outdoor Shower

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

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

Ceiling Fans

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

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

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


Cypress Sky

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

Private Washing Machine

Private Dryer

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

River & Vine

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

A Tuscan Beauty

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

Espresso Machine

Bicycles

Hammock

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

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

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

Outdoor Fireplace / Firepit

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

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

The Charms of Chianti

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

Offering views of the surrounding hills and the owner's vineyard, this eco-friendly villa is set within the Chianti countryside. While the interior is fairly subdued and the unpaved road leading here isn't the best drive, this home promises a paradisal outdoor living space. You'll find a poolside dining area and a hot tub in the garden, plus you can enjoy fresh produce from the chicken coop and vegetable patch. Exploring Tuscany? Gaiole is two kilometres away, and Radda is eight.

Tuscan Idyll 

Escape to the tranquillity of the Tuscan hills when you stay at this two-bedroom home. Inside, the rooms are simply styled with country character, including a cosy living space and a homely kitchen. Stepping outside, there’s a private terrace tucked among the garden greenery (the best spot for a glass of local Chianti wine), and a little further away you’ll find a sunny shared swimming pool. Ready to explore your scenic surroundings? Siena, Florence, and San Gimignano are all within day trip distance, or you could spend an afternoon cycling through vineyards and olive groves. If that sounds like holiday heaven, then this is the home for you.

The Etruscan View

This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence. The private pool is perfect for a refreshing dip, while the shaded dining areas invite you to savour leisurely meals alfresco. With its blend of traditional features and elegant touches, this home provides a romantic and restful escape.

Tuscan Cottage

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

If you’re looking for an escape from it all, this could be the home for you. Set on a private road deep in the woods, this Chianti villa has tranquillity running through its core. We love the seamless blend of modern furniture with the traditional building here, but the outdoor space is our biggest winner. Sun-kissed terraces, a hot tub, a private pool, alfresco dining areas – what’s not to love? If you can tear yourself away, it’s a mere ten-minute drive to the wine-making town of Gaiole, which is well worth a visit. 

The Chianti Grape

Board Games

Children's Dinnerware

Tennis Court

Workplace

Self Check-in / Check-out

Fenced Garden

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

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Security Cameras

Nestled in the Chianti countryside between Siena and Florence, this home has serenity running through its core. Sat atop a hill, surrounded by olive groves and vineyards (the site is actually an active organic winery), it’s impossible not to relax here. Inside, this traditional home has been respectfully renovated to offer a homely retreat which is ideal for families and groups of all sizes, while the outdoor space is sure to be a hit with all. A private pool, sun-drenched terraces and alfresco dining opportunities – including a wood-fired pizza oven for authentic Italian cuisine – what’s not to love? 

Chianti Sunset

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

Lounge by the lavender-edged 18-metre lap pool with its beautiful views of the forested hills and distant hilltop village of Castagnoli. You can’t see the pool from the house, as it's 70 metres down a track, past the owner's villa – but once there, it’s a sight to behold. Or relax on your terrace or balcony in the private garden. It’s the perfect spot for an Italian feast cooked on the barbecue or rustle up something in the kitchen on the first floor with its marble worktops. If you need to top up on ingredients, then Gaiole, 4 kilometres away, has a selection of shops, as well as restaurants, while the nearest village, Barbischio, 1 kilometre away, has a superb trattoria. 

The Vines of the Vineyard

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

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

With rolling Chianti hills all around, this traditional villa couldn't feel more Tuscan if it tried. Comprised of a main house and three en-suite bedroom cottages, it's perfect for a large family getaway. While the bathrooms could do with an update, and some of the interiors feel dated, it's all beautifully cared for. Kids will love you for the private pool with dive board –⁠ a fifty-metre flip-flop from the main house. There's also a bocce court and a ping-pong table, and you're welcome to pick fresh vegetables and eggs from the gardens and chicken coop. Location-wise, you're just 5 kilometres from the traditional Chianti towns of Radda and Castellina.

Chianti Memories

Amidst the vineyards and olive groves of Tuscany, this winery estate perfectly embodies the magic of its location. Enjoy idyllic views and slow days relaxing by the private pool. There’s an outdoor kitchen with a pizza oven for memorable evenings under the stars. Inside, the rooms are set across the main house and the adjoining cottage – making this a great option for groups and families looking to stretch out and spend quality time together. You’ll also be perfectly placed for adventures across the Chianti Classico region. It's also just a twenty-minute walk into the heart of Greve in Chianti, where you’ll find a great selection of artisan shops, restaurants and patisseries.  

The Vineyard Dreams

With far-reaching views of the rolling Chianti hills, it’s impossible not to relax in this villa. Traditional yet modern, this home promises a true taste of Tuscany, alongside plenty of space to relax. We love the three tiered terraces, each offering something different – alfresco dining on the top terrace, bowls on the middle, and a private pool on the lower. And, being situated next to a working winery, you’re perfectly placed for a spot of wine tasting and some authentic Tuscan food – all of which can be organised by your host. 

Chianti Splendour

Book a stay in one of the best homes in Volpaia

We selected the 3772 homes worth renting in this location

Who's coming along?

Home spotlights in Volpaia

We selected the top 3% holiday homes in Volpaia

Most popular homes in Volpaia

Check upcoming rates & availability for Volpaia

Frequently asked questions