Italy - Holiday Rentals in Chianti Italy

Country: Italy (10548) | Region: Tuscany (3343)

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Found 130 Chianti holiday homes for rent

Radda in Chianti, House for rent

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

Booked

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Castellina in Chianti, Apartment for ren

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

Booked

Available

Castellina in Chianti, Apartment for ren

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

Booked

Available

Radda in Chianti, Apartment for rent

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

Booked

Available

Radda in Chianti, Apartment for rent

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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Radda in Chianti, Apartment for rent

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

Booked

Available

Castellina in Chianti, Apartment for ren

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

Booked

Available

Castellina in Chianti, Apartment for ren

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

Booked

Available

Castellina in Chianti, Apartment for ren

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

Booked

Available

Radda in Chianti, Apartment for rent

Apartment • 6 People • 3

• 4

•

From

€

988 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 988 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Fruits of Chianti

Nestled within the iconic green hills of Tuscany, close to the charming hilltop town of Radda, this beautifully restored farmhouse has everything you need for a good time – delicious food, great wine and quality time with loved ones. Both the interior and exterior boast traditional features, with wooden-beamed ceilings, terracotta tiles and exposed brick creating a cosy atmosphere and a sense of authenticity. The lawn is beautifully kept and offers a private pool and outdoor shower, which provide an invigorating start to the day. Once you're feeling refreshed, it's time to explore – get the mountain bikes out from the bike shed and go for a scenic cycle into town for a cultural adventure. This quintessential Tuscan town is home to upmarket boutiques, art galleries and 360-degree panoramic views thanks to its high position. Wine lovers will be in their element in Chianti – we highly recommend spending an afternoon wine tasting in one o...More Details

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

Found 130 Chianti holiday homes for rent

Radda in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Chianti Property for rent