Radda in Chianti

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Entertainment

Bathtub

Hair Dryer

Bathroom

Coffee Maker

Cooking Essentials

Dishwasher

Freezer

Fridge

High Chair

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Kitchen & Dining

Cot / Crib

Dryer

Washing Machine

Bedroom & Laundry

Outdoor Pool

Private Pool

Swimming Pool

Wellness & Fitness

Laptop Friendly Workspace

Wi-fi

Internet & Office

Fireplace

Heating & Cooling

Private Parking

Parking Available

Private Entrance

Parking & Access

Barbeque

Beach / Pool Towels

Fenced Property

Garden

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Outdoor

Mosquito Net

Nice to haves

Child Friendly

Other

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

Air Conditioning

Balcony

Pets Allowed

Pets

If you fancy living like a Tuscan local, this chic townhouse in the heart of Radda will be right up your street. Set across three floors, it’s an ideal base for two couples, with the bedrooms on separate floors and the living area in between, allowing plenty of opportunity for privacy, or to come together to socialise. Location-wise, you’re in for a treat. Wander into town to pick up some freshly baked bread, or dine out daily at one of the many authentic Italian eateries nearby – there’s something for everyone here. 

Chianti Classic

Cafetiere

Iron

Ironing Board

Desk

Central Heating

Free Parking On Premises

Courtyard

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

Pod Coffee Machine

Balcony / Patio

Safe

Peace and placidity await you at this authentically Tuscan bungalow. It sits in a serene countryside spot in Radda in Chianti, just a short stroll from some lovely shops and restaurants in the heart of the village, while also being a drive away from Florence and Arezzo for delightful day trips spent exploring their historic streets. We love the outdoor areas of this home – there's a private pool for blissful swims in the sunshine, and the covered terrace makes a wonderful place for sipping on cocktails at sunset.

The Chianti Hill

Sound System

Rain Shower

Toaster

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

Free Parking

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens. There’s a separate cottage for guests seeking a little extra privacy, while the outdoor terrace is perfect for sharing Tuscan dishes all together (your host even produces their own olive oil and wine). Located near the village of Radda in Chianti, you’re perfectly placed for hiking the Tuscan hills or visiting one of the many vineyards that the region is known for.

The Rosso

Satellite / Cable TV

Board Games

Library of Books

Toiletries

Blender

Children's Dinnerware

Espresso Machine

Ice Machine

Kettle

Extra Pillows and Blankets

Hangers

Bicycles

Exercise Equipment

Tennis Court

Workplace

Self Check-in / Check-out

Fenced Garden

Hammock

Outdoor Fireplace / Firepit

Outdoor Shower

Umbrellas

Fire Extinguisher

First Aid Kit

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

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

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

Sauna

EV Charger

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

Hot Tub

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

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

This rustic stone villa is located just a short stroll from the historic centre of Gaiole, surrounded by world-class vineyards and sun-drenched olive groves. The traditional building has been thoughtfully restored and now boasts contemporary decor alongside many of its original features. And outside you’ll find plenty of serene spots to soak up the countryside views, from a private pool to an alfresco dining terrace. Because of the layout of this home and garden, we think it’s best suited to groups of friends or families with older children.

Tuscan Memories

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

Ping Pong Table

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

In the Chianti hills, this villa offers vineyard views and easy access to the region's many wineries and picturesque towns. We love the garden – it's where we reckon you'll spend most of your time. There's a private pool, an alfresco dining terrace, and a pool house with a gym that fitness buffs will appreciate. Indoors, the antique furniture and traditional features may feel a bit dated, yet they're all part of its charm. As for location, you'll find Gaiole, Radda, and Castellina a short drive away, making it an ideal base for Tuscan adventures.

Sangiovesece Scenery

Heated Towel Rail

Drying Rack

Tucked away in the Tuscan countryside, this idyllic villa promises plenty of rest, relaxation and rustic charm. Famous for its rolling hills, acres of vineyards and quaint, historic hamlets, there's no better spot to explore all this region has to offer. Both Florence – an hour away – and Siena – a thirty-minute drive away – are great options for day trips, though it will be hard to pull yourself away from the serene gardens back at home. Enjoy your morning espresso on the cosy outdoor sofa, go for a relaxing swim in the pool and soak up the sun on the poolside lounge chairs. Surrounded by olive trees, rose bushes and dense woodland, you'll feel a sense of calm wash over you as you take it all in. Even inside, the bright, classically styled rooms feel warm and welcoming. Whether you're whipping up meals in the mint-green kitchen – which are best enjoyed alfresco – or snoozing in the comfy elegant bedrooms, you'll love calling this hideaway your home away from home.

Wild Roses

DVD Player

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

Smart TV

Foosball / Table Football

Bathrobes

Luxury Toiletries

Private Washing Machine

Private Dryer

Black-Out Blinds

Cleaning Products

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Jacuzzi

Electricity Adaptors

Multiple Sets of Keys

Fenced Pool

Herb Garden

Outdoor Audio

Outdoor Bathtub

Throws

Welcome Hamper

Pet Bowls

Surrounded by vineyards tumbling down hillsides and towering trees, this stone villa sits in the heart of the Chianti Hills. The beautiful village of Lecchi with its ancient castle is just a six-minute drive away if you’re not too busy discovering the family-run wineries and vineyards on your doorstep.

This villa was designed for entertaining, inside and out. In the lush garden, you’ll find seating for a huge group, shaded by a pergola. Perhaps unwind in the hot tub after a session in the gym. There’s also a sauna for post-workout relaxation. If swimming laps is more your style, there’s a shared swimming pool at the bottom of the estate, lined with loungers.

Inside, the grand lounge is set around an old hearth, just like you’d expect in a traditional old Tuscan farmhouse. Wooden ceilings and terracotta floors are a nod to the past, while the pops of vibrant colour throughout keep things lively and modern. Especially in the dining room, where lime and bottle-green combine at the banquet-sized table. In the spacious bedrooms, wrought-iron and four-poster bedframes add a touch of old-world charm too.   

My Chianti Heart

Gated Community

Set in a hamlet among vine-covered hills, this home is one of eleven houses, with origins dating back to 1400. There’s a flower and plant-filled private garden and shaded terrace perfect for alfresco meals, while the beautiful large pool is shared – it’s located a short stroll from the home and has incredible views. Inside the cottage, it’s quite traditionally styled, as you’d expect and there’s a fireplace, for when the weather turns cold. With all the wonderful vistas, you may be happy staying put, but that would be a shame, as the charming town of Radda with its narrow cobbled streets, is just a few kilometres away.

The Olive Dawn

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. 


Tuscan Whisper

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

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

Escape to this Tuscan house that offers a rural setting and traditional features. Located just outside one of Chianti’s oldest hamlets, Vertine, this villa is ideally situated for exploring the quaint villages and wineries – speak to your host if you’d like to arrange a tour. From playing boules, basketball or billiards, to relaxing in the hot tub and sauna after a day by the pool, this home offers an idyllic setting to unwind with family and friends. When it comes to mealtimes, not only will you find two kitchens, but you can cook organic produce straight from the garden and enjoy fresh eggs from your host’s hens.

The Tuscan Vine

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

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

Surrounded by Chianti countryside, this home has tranquillity running through its core. Ideal for a couple on an Italian getaway, we love the private terrace here – just the spot to enjoy undisturbed quality time with your loved one, whether sunbathing, dining alfresco or raising a glass in a toast to your holiday. When the heat gets a little much, the shared pool offers the perfect respite. Locally, San Sano village is within walking distance, or you can drive a mere fifteen minutes to explore beautiful Radda. 

Oak & Vine

Carbon Monoxide Detector

Smoke Detector

Nestled between the pretty hilltop towns of Chianti, this home offers a traditional Italian sanctuary. Enjoy breathtaking views across vineyards while relaxing on the terrace. There’s a private pool for blissful swims and an original stone oven for authentic pizza nights. Inside, you’ll find plenty of space for entertaining with a wine tasting room, a cosy living room and a games room. Your host can also help organise a range of sweet extras – including a private chef, guided tours and walking excursions. And when it comes to explorations further afield, it’s just a short drive to the nearest amenities, while Florence and Siena are also within easy driving distance. 


The Tuscan Moon 

Shared Washing Machine

Housed within a complex of stone buildings that were once a wine and olive oil-producing estate, this home offers Tuscan relaxation in spades. A communal pool, children’s pool and tennis courts await in the shared grounds, while the private terrace with its countryside views is perfect for a celebratory sundowner after a day of fun and exploring. The traditional interiors may not suit those looking for a flashy modern stay, but beamed ceilings and tiled floors add a touch of rural charm here. While you could easily while away the whole day on-site, take a hilly stroll to the nearby village of Lecchi or hop in your car for a day trip to Siena, Florence or San Gimignano.


Toscana Per Sempre

This 17th-century villa in the heart of the Chianti countryside offers far-reaching views across the vineyards and olive groves out to Siena. You're within walking distance of Lecchi, as well as being a fifteen-minute drive from Radda in Chianti for dreamy day trips exploring the region. A car is recommended to get the most out of your stay here. Outside, you'll find a well-kept garden lined with cypress trees, as well as a private pool. But our favourite spot has to be up on the dining terrace, which provides some beautiful views over the hilly surroundings and is ideal for alfresco feasts together.

Chianti Belle

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

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 

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

Heated Pool

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

With majestic views across rolling hills and olive groves, this home makes it easy to enjoy the magic of Italy. Set within a working winery, you’ll be treated to an authentic taste of rural life along with all the essentials you could need to slow down and spend quality time together. There’s a private swimming pool and a terrace for alfresco dining. The rooms are set across the main house and two independent apartments – making this a great option for groups looking for space to stretch out. Your host can help organise a range of sweet extras such as private chefs and guided tours. Plus, there are beautiful hiking trails straight from the door and it’s just a short drive to the historic towns of Castellina and Radda, as well as the city of Siena.

The Tuscan Muse

Rooftop Terrace

This Tuscan cottage can be found amid beautiful gardens with views of the gently rolling hills. The land used to be a vineyard, but has been restored into a resort of cottages and apartments in the style of an authentic Tuscan hamlet – the result is charming. This petite home is rustic and traditional, so the decor won’t be to everyone’s taste – and the steep spiral staircase might prove tricky for some. But beyond that, you can look forward to a shared outdoor pool and tennis court, a hot tub, and a lovely dining terrace. You can stroll into the village of Lecchi in Chianti, and the popular town of Radda in Chianti is just a fifteen-minute drive. 

The Chianti Way

Temperature Control

Underfloor Heating

This beautiful home is a secluded base in Chianti. It’s surrounded by the hills and vineyards of the countryside and boasts 180-degree views. You can admire the vista from the private pool and the outdoor dining terrace, a splendid spot for an alfresco meal – speak to your host about hiring a private chef. Inside, you’ll find traditional Tuscan features including beamed ceilings and terracotta tiles. When you’re not lounging beside the pool or visiting nearby vineyards, you might drive forty minutes to Siena for a day trip. 

Paolo's Vine

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