Castellina in Chianti

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Entertainment

Bathtub

Hair Dryer

Bathroom

Dishwasher

Fridge

High Chair

Kitchen

Kitchen Utensils

Microwave

Oven

Pod Coffee Machine

Freezer

Kitchen & Dining

Cot / Crib

Washing Machine

Bedroom & Laundry

Outdoor Pool

Shared Pool

Swimming Pool

Wellness & Fitness

Wi-fi

Internet & Office

Air Conditioning

Fireplace

Heating & Cooling

Free Parking

Parking Available

Parking & Access

Barbeque

Garden

Outdoor Seating

Patio / Terrace

Outdoor

Mosquito Net

Nice to haves

Child Friendly

Other

This charming cottage is tucked away on an authentic working vineyard, beside a family farmhouse. It’s just 1 kilometre from Castellina in Chianti, and within driving distance of Sam Gimignano, Siena, and Florence – you’ll have plenty of options for day trips. There’s a sloped garden with a furnished terrace and a shared swimming pool, and exquisite views of the Chianti countryside to be enjoyed from almost every angle. The cottage feels typically Tuscan, with its terracotta tiles and wooden beams. It’s a comfortable holiday home in an idyllic setting. 

Il Nocino

Coffee Maker

Stove

From the countryside views to the traditional character inside, there's no denying that this home is unmistakably Tuscan. It's situated among a working vineyard, offering access to the estate's communal pool and a shared garden. The cottage itself has its own terrace, ideal for relaxing in the fresh air while sharing a bottle of Chianti wine. Some rooms are a tad dated, but there's ample space to relax. When you're ready to venture out, an array of wineries and picturesque villages are within driving distance. Florence, Sienna, and Arezzo are also about an hour away for adventures further afield.

Tuscan Orgins

Private Pool

Private Parking

Private Entrance

Balcony / Patio

Sun Loungers / Beach Chairs

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

Ping Pong Table

Heated Towel Rail

Rain Shower

Cafetiere

Toaster

Sauna

Laptop Friendly Workspace

Central Heating

Free Parking On Premises

Helipad

Courtyard

Fenced Property

Outdoor Shower

Sun Umbrellas

Pets Allowed

Pets

You can arrive in style at this palatial farmhouse fringing the hilltop commune of Castellina (2.7km) - there's a private helipad should you need it. Set within easy driving distance of Siena, San Gimignano and Florence for day trips, and with the bustling restaurants of Castellina close by, it’s an excellent base to explore Tuscany. There are plenty of reasons to linger at home, too – starting with those monumental views from the wraparound loggia for alfresco dining. Kids will love you for the private pool, gently sloping lawns for a runabout and table tennis. Meanwhile, adults can factor in some downtime in the private sauna.   

The Valley

Beach / Pool Towels

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

Hot Tub

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

Safe

This stone-built villa in the heart of Chianti boasts stunning views of the valley and vine-clad hillsides from almost every room. Perfect for two couples wanting to holiday together without crowding each other, each en-suite bedroom feels self-contained, with a kitchenette for morning cuppas. Meanwhile, the free-flowing living spaces downstairs and a private pool with a view are all about socialising. Fringing one of the main Chianti towns, Castellina (a 7-minute drive), there are bars and restaurants close by for evenings out, and you’re just a short drive from Siena and Florence (both less than an hour away).

A Little Bit of Chianti

Satellite / Cable TV

Cooking Essentials

Kettle

Hangers

Iron

Ironing Board

Drying Rack

Balcony

Fenced Garden

Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright interior, where farmhouse simplicity meets elegant design in the living room. With its giant hearth, plump sofas and tiered chandelier, this is the perfect spot for socialising over a glass of wine or curling up by the fire with a good book on cooler nights. With four comfortable bedrooms boasting postcard-like countryside views and a farm-style kitchen full of traditional charm, you’ll have everything you need to make yourself right at home. Head outside to take cool dips in the pool, or sit back in one of the many sun loungers while taking in the spectacular hillside views. Wander around the vineyards, visit Castellina in Chianti (less than ten minutes away by car), then come back home for a barbecue under the pergola paired, naturally, with a glass of Chianti. 

First Of The Summer Wine

Dryer

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

Exercise Equipment

Carbon Monoxide Detector

Fire Extinguisher

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 

Toiletries

Once owned by winemaker Marchesi Torrigiani, this beautiful hillside villa still features the vineyards that were once, and will likely always be, the heart of this farmland. A beautiful sight, it’s only marginally rivalled by the view of the Chianti Hills which is sprawled out right before you from the elevated position of this home. When you walk the grounds in search of new angles to photograph, you might stumble upon a wood-burning oven and picnic style-benches. Get the family together and venture down to barbecue lunch and dine alfresco in the shade of the towering trees. 

With another home on the property, you’ll likely make new friends around the communal pool when you’re spending lazy days in the sunlounger. Catch up on a novel, drink in hand, as the aroma of olives from the nearby tree drifts to you on the breeze.

Away from the home, you can find the mediaeval village of San Donato only minutes away. Walk the winding streets, marvel at the architecture, and sit down at one of the local restaurants for a beautiful lunch before returning home for an afternoon nap, followed by a glass of chianti wine out on the terrace.

Vineyards & Red Earth

Free Parking On Street

Stylishly rustic, this country home sets the tone for a restorative retreat in the heart of Chianti. Dating back to the 10th century, the house has a wonderful sense of character with plenty of space for groups to relax and enjoy the garden views. There’s also a private swimming pool and a terrace – perfect for alfresco dining. Your host can help organise a range of extra services here, including private chefs and guided tours – a great option for those looking to explore the region. From here, it’s just 4 kilometres to Castellina, while cities such as Florence and Siena are also within driving distance. 

A Touch of Chianti

Shared Washing Machine

Shared Dryer

Gated Community

You've got all the perks of a private home combined with the palatial shared grounds of a hamlet at this apartment complex nestled between the Chianti villages of Panzano and Castellina. The views of the rolling hills and iconic cypress trees are delightful from the estate's shared swimming pool. But if you're after more privacy, the panoramas from the apartment's private terrace are just as impressive. Besides a restaurant in the neighbouring village of Piazza, there are no local amenities to walk to. You'll need a car to explore but prepare for a hilly, uneven drive at times.  

Cheers to Chianti

Blender

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

Library of Books

Sound System

Black-Out Blinds

Cleaning Products

Extra Pillows and Blankets

First Aid Kit

Experience the beauty of Chianti with a stay in this luxurious Tuscan retreat. Owned by a family for more than a hundred years, now you’re invited to step inside and make your own special memories. From the private woodland and wildflower meadows to the outdoor swimming pool, you’ll find everything you could need to settle in and unwind. A member of the royal family designed the rooms and we don’t think you’ll be disappointed. Plus, your host is on hand to help organise a range of extras – including a private chef and wine tasting. And for explorations further afield, it’s just a short drive to Siena and Florence.


Being of Beauty

Parking On Street

Single-Level Home

Breakfast Included

This cosy apartment is located in the heart of historic Fonterutoli, surrounded by beautiful Tuscan countryside. Spend your time visiting local vineyards and wineries, or take a day-trip to Siena. The apartment has a classic Tuscan stone facade, which adds to the charm. Inside, you’ll find a fuss-free home that’s equipped with everything you might need for a short break. We think the best feature is the outside area, where you can sit in the shade of the trees and admire the stunning view. 

Wild Onion

Situated on the first floor of a traditional Tuscan stone building, this apartment puts you right at the heart of rural Tuscany, surrounded by glorious rosemary bushes, grape vineyards and olive groves. Here, you'll enjoy access to the site's fantastic communal facilities, including a terrace area with seating where you can gaze out at the countryside views, plus an outdoor swimming pool that's surrounded by loungers for afternoon naps. Inside, you'll find traditional Tuscan decor that makes the home feel warm and welcoming.

Grape Juice

Desk / Workplace

Herb Garden

If you dream of tucking yourself away somewhere in remote Italy, and indulging in nothing but pappardelle pasta, limoncello, and local wines, you’ve come to the right place. This traditional Tuscan home, perched in the idyllic Chianti hills, offers the simple pleasures of rural Italian life. We love the home’s exposed natural stone and brick, veranda canopies, and la bella vistas, beckoning you to adopt the pace of nature and unwind with your friends or family outdoors. Take a dip in the infinity pool, before drying off on a sun lounger overlooking sweeping views of the green woodlands, fields, and olive groves below. When dinnertime arrives, dine alfresco in the gentle shade of the charming patio area, surrounded by cypress trees and terracotta pots. 

Inside, a cute country-style kitchen with stone sink and traditional bread oven turned gas stovetop looks like the kind of place nonna would hand-shape pasta. Wood-beam ceilings and thick stone walls keep everything cool and rustic. With its prime location, you can explore the quaint town of Castellina and the surrounding hills with ease. Steeped in a long history reaching back to the Bronze age, the town’s winding roads will take you through an area well-known for its glorious local cuisine, wine tasting and awe-inspiring sunsets. 

Bellissima

Cosy and quaint, this typically Tuscan apartment is part of a pretty collection of homes, all set inside some historic stone buildings that feel charming and characterful. As such, you'll find terracotta tiled floors, farmhouse-style furniture and exposed stonework, all creating a snug and serene vibe. Staying here means you'll get access to some fantastic shared facilities on site, including a seating terrace with some spectacular views out to the surrounding countryside, as well as an outdoor pool that's ideal for hanging around on hot days. 


A Taste of the Hills

After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyone’s taste, but there’s no denying the beauty of the outdoor space. And, where better to cool off in the Tuscan heat, than the private pool? If you’re not dining alfresco and soaking up the countryside views, take the short drive to Quercegrossa for some authentic Italian food with the locals. 

Dreaming of Chianti

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

Espresso Machine

Self Check-in / Check-out

This 19th-century Tuscan farmhouse that sits 450 metres above sea level has been brought into stylish 21st-century style, all while retaining its rustic charm and characterful Italian romance. Featuring its original windows and tall beamed ceilings alongside contemporary decor, it’s a space that’s been reimagined with rest and relaxation in mind, not to mention a showstopping outdoors that is certain to have you basking in its beauty from dawn till dusk. 

Covering 1,200 square metres of land, the home’s terraced gardens are as expansive as they are stunning. Spend afternoons taking dips in the private pool before sunning yourself on one of the loungers, relishing the scent of the citrus and olive trees perfuming the air. When hunger calls, make your way to the white-draped pergola and fire up the barbecue for a memorable alfresco feast. As the sun begins to dip behind the surrounding hills, watch the stars come out one by one over a glass of wine before heading back inside for a dreamy night’s sleep. 

Should you wish to venture out for a day of exploring, you'll find the medieval village of San Donato a stone's throw away, while Barberino Tavarnelle is also just a short drive from your home. Alternatively, take the scenic Chiantigiana road that links the Chianti area, stopping off in Siena (about 40 km) and Florence (about 30 km), as well as the picturesque towns of Radda, Gaiole, Greve and Panzano, each boasting a wealth of stunning landscapes, historic churches and Renaissance villas. 

Tales of Sunsets

Tennis Court

This home is located in the medieval village of San Donato in Poggio and offers stunning views of the Chianti hills. The property features a large park, vineyards and a wood-burning oven and a barbecue on the wide terrace. There is also a swimming pool under nicely smelling olive trees. The apartment has two bedrooms, a bathroom with shower and a kitchen-living room with a sofa bed.

The Papessa

Board Games

Children's Dinnerware

Private Dryer

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Outdoor Fireplace / Firepit

Outdoor Kitchen

Umbrellas

Welcome Hamper

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

This gorgeous home boasts its own private pool and breathtaking valley and vineyard views. Ideal for families and large friend groups, there's plenty of space indoors and out. You'll find a games room and a gym, plus a volleyball court and several alfresco dining spots spread over the main house, the extensive gardens, and the separate basement. Wine aficionados can do some tasting in the cellar, and there are ten wineries within 5km. The location is fantastic for enjoying some peace and quiet alongside the picturesque views, but when it comes to exploring you'll find Siena only 15km away, and San Gimignano and Florence are also reachable by car.

The Vine Vineyard

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

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

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

Sitting on the hillside in Chianti's countryside, this apartment is part of a small collection of cottages and apartments. Typically Tuscan, the interior may be a tad dated – and you'll have to share laundry facilities – but it'll suit those craving a bit of character. You'll also have access to all the on-site amenities, including a communal terrace for alfresco dining and a shared swimming pool open from May to September. We highly suggest hiring a car here, as you'll want to get out and about to explore the local area. Vineyards, charming hamlets, and sightseeing hotspots like Florence and Castellina are all within easy reach.

Chianti Rosemary

Ice Machine

Bicycles

Desk

Workplace

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

Over the Chianti Hills and far away lies an abundance of Tuscan charm and Mediterranean serenity. Set in the ancient medieval village of San Donato, you'll get a quintessential Italian countryside experience with captivating views over the Tuscan landscape to remind you of your dreamlike location at every opportunity. 

The perfect escape for a couple or pair of travellers, the apartment brags a roomy kitchen, dining and living space with a separate bedroom and bathroom too. Of course, you'll also have access to the communal amenities shared with other guests. This includes the outdoor swimming pool, tennis court, terrace and barbecue areas, and picturesque property gardens. 

Sit and enjoy the spectacular landscape views under the olive trees with a glass of local wine. Against the gorgeous backdrop of the Tuscan rolling hills, the air is fragranced by vines and fruit orchards, setting the scene like a summery afternoon dream. 



Over the Chianti Hills

Pool House

Rooftop Terrace

This former lookout tower once guarded the passage between Florence and Siena. Today, it exists as a calm sanctuary offering idyllic views, a private pool and serene grounds. The rooms are spread across the main house and two independent apartments – making this a great option for groups looking to stretch out and socialise. All of the bedrooms have air conditioning and it’s a sweet option for families with plenty to explore in the surroundings. You will need a car to get around here, but it’s just 3 kilometres to Castellina in Chianti, while Siena is just a forty-minute drive away.

An Italian Tale

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

Smart TV

Foosball / Table Football

Bathrobes

Luxury Toiletries

Private Washing Machine

Jacuzzi

Electricity Adaptors

EV Charger

Multiple Sets of Keys

Fenced Pool

Outdoor Audio

Outdoor Bathtub

Throws

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

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