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

Library of Books

Heated Towel Rail

Luxury Toiletries

Rain Shower

Toiletries

Espresso Machine

Ice Machine

Juicer

Kettle

Toaster

Wine Cellar

Private Washing Machine

Private Dryer

Cleaning Products

Laundry Supplies

Luxury Bedding

Heated Pool

Temperature Control

Secured Parking

Outdoor Fireplace / Firepit

Outdoor Kitchen

Located in the heart of Tuscany, this expansive villa spans fifty hectares and is ideally suited for families or groups of friends. A tasteful blend of traditional features and luxurious interiors include impressive stone fireplaces, rustic wooden beams, and French doors. Enjoy alfresco dining for up to twenty guests, or spend your day lounging by the heated infinity pool, accompanied by the sound of the nearby river. With such a serene setting, it’s easy to forget that the Chianti region — with its wealth of places to see and things to do — lies just beyond the door.

Jade Hamlet

Netflix

Piano

Sound System

Streaming Services

Bathrobes

Wine Cooler

Black-Out Blinds

Drying Rack

Extra Pillows and Blankets

Hangers

Vacuum Cleaner

Exercise Equipment

Electricity Adaptors

Printer

Workplace

Ceiling Fans

Underfloor Heating

Free Parking On Street

Multiple Sets of Keys

Fenced Garden

Herb Garden

Rooftop Terrace

Breakfast Included

Welcome Hamper

Pet Basket

24-Hour Security

Carbon Monoxide Detector

Fire Extinguisher

Security Cameras

Security System

Smoke Detector

This beautiful 450-year-old villa boasts a majestic setting in Tuscany. Its Radda in Chianti location puts you within easy reach of vineyards and historic towns and villages, whether you plan on exploring by car, on foot, or by bike. You can look forward to breathtaking views of the rolling hills; the terrace is a splendid spot for sunset vistas, as is the private swimming pool. The villa has been expertly restored to blend old-world charm with modern luxury – think smart lighting and a state-of-the-art heating system alongside Carrera marble and traditional wooden beams. You won’t want to leave. 

Savour the Tuscan Sun

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

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

DVD Player

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

Satellite / Cable TV

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

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

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

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

Playground

Pool / Snooker Table

Sauna

EV Charger

Lift Access

Alarm System

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

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

Board Games

Children's Dinnerware

Umbrellas

First Aid Kit

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

Bicycles

Tennis Court

Self Check-in / Check-out

Hammock

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

Hot Tub

Free Parking

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

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 

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

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

Parking On Premises

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

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

DVD Library

Games Room

Safety Gates

This 400-year-old luxury farmhouse sits in the Chianti hills between Florence and Siena. Up on a hilltop, the view over the forest-clad countryside is simply sublime, from secluded seating nooks around the garden and from the 12-person dining table on the patio. Alfresco dining is a cinch thanks to a wood-fired pizza oven and barbecue area. An infinity pool invites you for a cooling dip and there’s a dedicated games room inside for evenings at the pool table. The group can spread out between two sitting rooms inside where the traditional farmhouse aesthetic blends with modern features. Wine-tasting sessions are on offer in the private wine cellar, arranged through your host.

Chianti Breeze

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. 


Tuscan Whisper

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

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 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

Bread Maker

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

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