Castellina in Chianti

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Satellite / Cable TV

Entertainment

Hair Dryer

Bathroom

Blender

Coffee Maker

Dishwasher

Fridge

Juicer

Kettle

Microwave

Oven

Toaster

Wine Cooler

Kitchen & Dining

Private Washing Machine

Private Dryer

Cot / Crib

Dryer

Iron

Washing Machine

Bedroom & Laundry

Indoor Pool

Outdoor Pool

Private Pool

Sauna

Swimming Pool

Wellness & Fitness

Desk

Wi-fi

Internet & Office

Air Conditioning

Heating & Cooling

Free Parking On Premises

Helipad

Parking Available

Parking & Access

Barbeque

Garden

Hammock

Outdoor Seating

Patio / Terrace

Outdoor

First Aid Kit

Smoke Detector

Other

This Italian villa caught our eye for its panoramic views of the Tuscan countryside. There’s plenty to make your holiday memorable here, including both indoor and outdoor pools, a sauna, and a private wine cellar. While the home is perfectly set up for a large group, you can still get privacy when you need it – all of the bedrooms are en-suite and the second floor of the villa has its own entrance, as well as an extra lounge and kitchenette. And when you’re ready to explore, why not book a wine tasting at one of the local vineyards, or take a scenic drive to the picturesque town of San Gimignano – famous for its medieval towers and gelaterias?

A Truffled Retreat

Bathtub

High Chair

Kitchen

Kitchen Utensils

Pod Coffee Machine

Freezer

Shared Pool

Fireplace

Free Parking

Mosquito Net

Nice to haves

Child Friendly

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

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

Ping Pong Table

Heated Towel Rail

Rain Shower

Cafetiere

Laptop Friendly Workspace

Central Heating

Private Parking

Private Entrance

Balcony / Patio

Courtyard

Fenced Property

Outdoor Shower

Sun Loungers / Beach Chairs

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

Cooking Essentials

Hangers

Ironing Board

Drying Rack

Balcony

Beach / Pool Towels

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

Piano

Toiletries

Espresso Machine

Self Check-in / Check-out

If you’re in search of a rustic retreat in the heart of Chianti Classico, this home delivers a sweet solution. You can enjoy stunning views across olive groves, vineyards and rolling hills. There’s a private pool for leisurely afternoon swims, a shaded pergola for evening meals and a billiard room for family-fun and games. The rooms are spread across the main house and an adjacent annexe – providing plenty of space to stretch out and socialise. You will need a car to get around here, but it’s just a short drive to Castellina in Chianti, while Siena and San Gimignano are both within easy driving distance. 

Classic Moments

Pool House

Rooftop Terrace

Safe

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

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

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

Library of Books

Sound System

Black-Out Blinds

Cleaning Products

Extra Pillows and Blankets

Exercise Equipment

Carbon Monoxide Detector

Fire Extinguisher

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

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

Bathrobes

Luxury Toiletries

Children's Dinnerware

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Heated Pool

Jacuzzi

Electricity Adaptors

EV Charger

Multiple Sets of Keys

Fenced Pool

Herb Garden

Outdoor Audio

Umbrellas

Welcome Hamper

Pet Bowls

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

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

Single-Level Home

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

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

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

Board Games

Outdoor Fireplace / Firepit

Outdoor Kitchen

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

Tennis Court

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

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

Smart TV

Foosball / Table Football

Ice Machine

Hot Tub

Outdoor Bathtub

Throws

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

Parking On Street

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

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

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

This apartment is part of a beautiful agriturismo in San Donato, in the heart of Tuscany. Views of the Chianti Hills can be enjoyed from almost every angle, and there are vast grounds so you can spend much of your time outside. The gardens and pool are shared with the other guests of the agriturismo, as is the wide terrace with its wood-burning oven and barbecue. You’ll be just a short drive from the ancient medieval village of San Donato in Poggia, a marvellous spot for lunch in a trattoria. 

Buona Giornata

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

In the heart of Chianti sits this stunning holiday home, perched up on a hill and featuring gorgeous views over the surrounding Siena landscape. It’s a classic stone villa with charming interiors and characterful features, such as ornate light fittings, retro tiled floors and elegant furniture. 

We love the lovely living area that has a fireplace that you can cosy up to on chilly evenings and the lavish dining space that’s great for feasting on pizzas and pasta dishes. You’ll be even more impressed with the outside, where you’ll find a beautiful outdoor pool where you can have an invigorating swim as the sun comes up, as well as loads of sitting areas to relax and admire the views out over the olive groves and vineyards around you.

When you want to head out, you’ll find yourself perfectly located for exploring Siena, as well as the medieval villages of Vagliagli, Radda and Gaiole where you’ll find an idyllic atmosphere and picturesque sights to see.

Chianti Chic

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

If you’re searching for somewhere to escape the hustle and bustle of everyday life, this Tuscan villa will be right up your street. Ideal for larger groups of friends or family, the countryside location is as peaceful as it gets. And with sunny spots for alfresco dining and a private pool, making the most of the Mediterranean climate is a breeze. Despite the location, you’ll find you’re only a few minutes’ drive from bustling San Donato, while the wine towns of Greve, Radda, and Castellina are within easy reach.

Chianti Nights

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

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 

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

Desk / Workplace

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

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