Internet Access Rentals Chianti Holiday rentals Italian vacation rentals of Apartments and Houses - Short term lettings

Apartment • 10 People • 5

• 3

•

From

€

700 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 700 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Chianti Calm

You’ll find this restored farmhouse in the heart of Chianti, surrounded by vineyards and olive groves. Spread across a main house and a separate cottage, this place is perfect for a group of ten to get together while still having plenty of space to spread out. The home is semi-detached, but the garden, swimming pool, dining terrace, and sun loungers are all yours. The rural location means a car is essential here, especially if you intend on exploring the surrounding towns and villages. We recommend visiting Siena, less than an hour's drive away. *Due to the location of this home, we recommend hiring a car. Please note, access to the property is via an unpaved road. *This is a semi-detached home – the neighbouring villa is occupied by local residents. *The outdoor space is for your exclusive use only. *The swimming pool (open from May to September) isn't fenced. If you're bringing little ones, they'll need to be supervised at all tim...More Details

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Apartment • 10 People • 5

• 6

•

From

€

831 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 831 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Memories

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. *There is ample private parking outside the villa. *The swimming pool is a fifty-metre walk from the villa. It is for seasonal use from May to October, weather permitting. There is a pool house with an additional shower room and an honesty bar. Guests can help themselves and pay upon c...More Details

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Castellina in Chianti, House for rent

Apartment • 4 People • 2

• 2

•

From

€

566 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 566 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

A Little Bit of Chianti

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). *There is ample private parking outside the home. It’s worth noting the approach to the house is on an unpaved lane. *A cot and high chair are available for little ones. *There are stairs within this home which may be unsuitable for guests with restricted mobility. *The private pool is for seasonal use, from May to October, we...More Details

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House • 8 People • 4

• 5

•

From

€

395 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 395 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

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. *There’s free parking at this home. *This home is spread over two floors so it may not be suitable for those with reduced mobility. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool is shared between the other homes on the property. It’s open from May-September. Air Conditioning Barbeque Bathtub Child Friendly Cot...More Details

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Castellina in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

461 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 461 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Orgins

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. *This home is on a family farm with another cottage, a main house, and a barn. You'll share access to the garden and swimming pool with other guests. *The communal swimming pool is open from May to September and is about 50 metres away from this home. *There's a bedroom and bathroom on the ground floor. This room's double bed can be converted...More Details

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Apartment • 8 People • 4

• 4

•

From

€

921 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 921 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

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. *This home is not suitable for infants or children under the age of 6. *It’s worth noting the approach to the house is on an unpaved lane, and a high-clearance vehicle is recommended. There is parking for three cars. *There's a separate cottage for guests seeking extra privacy. It features a living area and...More Details

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House • 14 People • 7

• 7

•

From

€

1,317 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,317 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Ode to Beauty

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. *Due to this home's location, we recommend hiring a car to get the most out of your stay. Please also note there is an unpaved, uneven road leading to the house so a high clearance vehicle is recommended. *There is private parking for up to five cars. *This home consists of a main house with six bedrooms, alongside an independent cottage with a kitchen, living room and a bedroom (located on the mezzanine level). *One pair...More Details

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House • 8 People • 4

• 4

•

From

€

729 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 729 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Eternal Etruscan

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. *This home consists of two apartments, each with its own living area and kitchen. They're connected by an outdoor staircase. *The traditional decor here might not be to everyone's taste. It feels a little dated in parts. *Two double beds can be converted into twins if needed. *If you're travelli...More Details

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House • 9 People • 5

• 4

•

From

€

734 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 734 /Night (minimum stay 1 night)

Swimming Pool

WiFi

A Guide to the Hills

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. *Due to this home's location, we recommend hiring a car to get the most out of your stay – there is also private parking for two cars. *Please note there is an external staircase between the ground and the first floor. Each floor has its own private entrance. *Two of the bedrooms can be arranged with double beds or two singles beds upon request. *There is no air-conditioning here but fans are provided. Please also note t...More Details

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House • 10 People • 5

• 6

•

From

€

5,401 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 5,401 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Sangria

At this rustic villa, rolling vineyards are on your doorstep. We mean that quite literally – the owners are local winemakers, and they offer tastings in the medieval tower-turned-wine bar. They'll also arrange welcome dinners, cooking classes, private chefs, continental breakfasts, and other special touches during your stay. As for the home itself, we think it's pretty spectacular. A private pool, sun-kissed garden, and Chianti views await outside, while the somewhat traditional interior has a few surprises in store – namely, a chef's kitchen, a small gym and a wellness centre boasting a Turkish bath and steamy sauna. Location-wise, Radda is less than 2 kilometres away, and Florence and Siena are great options for day trips. *The fifth bedroom is located in a guest annexe. It has a kitchen, double bedroom and bathroom.*Daily housekeeping (excluding Sundays) is included. Bath towels are changed daily, while pool towels and bed linen ar...More Details

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Apartment • 8 People • 4

• 3

•

From

€

1,951 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,951 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

A Touch of Chianti

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. *Due to this home's location, we recommend having a car to get the most out of your stay – please also note there is a 200-metre track leading to the entrance. *A complimentary mid-stay housekeeping service is included with your stay. *This home is spread across two floors with no internal lift. Please also note one of the bedrooms is...More Details

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Apartment • 6 People • 2

• 1

•

From

€

204 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 204 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Dreamers

This apartment is a comfortable base from which to explore all that Tuscany has to offer. Siena, around 27 kilometres away, is an ideal day trip destination, while the small town of Castellina in Chianti is just a short drive away. The home’s rustic interior design won’t be to everyone’s taste as the place feels a little dated in parts, but access to a communal swimming pool and barbecue area certainly makes up for it. If you’d like to make your mornings extra special, your host provides breakfast for an additional fee. *Due to this home's location, we recommend hiring a car to get the most out of your stay. Parking is available on the premises. *Heating and the use of Air Conditioning are charged extra upon consumption. *The communal swimming pool (open from the 1st of May to the 1st of October) isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *Your host can also provide a high chair, at no ...More Details

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Apartment • 6 People • 3

• 3

•

From

€

801 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 801 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Stonehill Vines

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. *All the beds can be separated or pushed together to make singles or d...More Details

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Apartment • 10 People • 5

• 6

•

From

€

1,357 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,357 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Wild Roses

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 hidea...More Details

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Apartment • 12 People • 6

• 7

•

From

€

1,821 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,821 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Classico

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? *You'll need a car to explore this area. There's free parking on site *The pool is open from the end of April to the beginning of October *Steps wi...More Details

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Apartment • 6 People • 4

• 4

•

From

€

1,348 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,348 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

First Of The Summer Wine

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...More Details

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Apartment • 10 People • 5

• 2

•

From

€

468 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 468 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Stuff of Dreams

With a truly picturesque location in the Chianti hills, this rustic villa is the ideal choice for anybody that has fantasised at any point about eloping to Tuscany for a short while — which is surely most people, right? Thanks to the elevated position, the address benefits from sweeping views of the countryside and these can be admired while dining on the terrace or gliding through the swimming pool, which is shared with the other four houses in the tiny village. Once you step through the home's large vaulted entrance — formerly the property's stables — you'll be greeted with an interior heavy on period features, including the fireplace, wooden ceiling beams and antique furnishings. The walls are covered in a great variety of artwork, while the four-poster beds add an extra touch of grandeur. When it comes to days out, you're firmly in wine territory here and there are local vineyards to visit not too far from the home. There are wal...More Details

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Apartment • 6 People • 3

• 2

•

From

€

473 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 473 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Brick - Green Shutters

There are many great things to say about this 18th century villa in Chianti, so let’s start with the most obvious, shall we? Overlooking the breathtaking Chianti Classico hills, the view here is something that shouldn’t be missed. We can picture it already, sitting out on the sunlounger simply basking in the sunshine and fresh air whilst you admire the incredible vistas. Then there’s the location itself which puts you on the doorstep of many of the finest wineries of the region. Sample all the farms and vineyards have to offer, or go on a hike when you’re in the mood to reconnect with nature. The interior of this home is another big tick – rustic but cosy, you’ll be especially drawn to the traditional Tuscan fireplace that, although ornamental, adds such warmth to the space. If it’s a fire you want, however, light it up in the barbecue outside where you can enjoy everything you brought back from the cellars and shops. *Due to the lo...More Details

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