Italy - Holiday Rentals in Chianti Italy

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

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Found 144 Chianti holiday homes for rent

Castellina in Chianti, Farmhouse for ren

Farmhouse • 16 People • 7

• 6

•

From

€

897 /night

Min Stay 7 nights

Castellina in Chianti, Italy

€ 897 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Credit Cards Accepted

10-room house 314 m2 on 2 levels. Comfortable and cosy furnishings: open living room with open-hearth fireplace and satellite TV. 2 double bedrooms, each room with air conditioning. Living room with open-hearth fireplace and satellite TV. 1 double bedroom with air conditioning. 1 small room with 1 bed and air conditioning. Open gallery with sloping ceilings with 1 bed and air conditioning. Living room with satellite TV. 1 double bedroom with air conditioning. Open kitchen (4 hot plates, oven, dishwasher, freezer). 4 showers/bidet/WC. Upper floor: open living/sleeping room with 1 double bed, open-hearth fireplace and satellite TV. 2 double bedrooms, each room with air conditioning. Open kitchen (4 hot plates, oven, dishwasher, freezer). 2 showers/bidet/WC. Gas heating, air-conditioning (extra). Terrace furniture, barbecue. Very beautiful view of the countryside. Facilities: washing machine, children's high chair, baby cot. Internet (WiFi...More Details

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Radda in Chianti, Apartment for rent

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

Booked

Available

Radda in Chianti, House for rent

House • 8 People • 4

• 4

•

From

€

803 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 803 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Vines - Vistas

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. *The main farmhouse is next to this home, which the owners use occasionally on weekends. However, they won't disturb you, always using a separate entrance and avoiding the pool area. *The swimming pool, available from May to October, isn't fenced. If you're bringing children, they'll need to be supervised at all times. *If you're travelling with little ones, your host can provide a free cot and high chair upon reque...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 • 12 People • 7

• 6

•

From

€

783 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 783 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

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. *T...More Details

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Available

Radda in Chianti, House for rent

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

Booked

Available

Radda in Chianti, House for rent

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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Available

Radda in Chianti, Apartment for rent

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

Booked

Available

Castellina in Chianti, House for rent

House • 12 People • 6

• 7

•

From

€

676 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 676 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Farmhouse Serenity

This renovated farmhouse sits within 460 hectares, in a dominant position in the hills of Chianti. It’s surrounded by vineyards and olive groves, and boasts far-reaching views across the countryside, but is just 5 kilometres from Castellina in Chianti and 20 kilometres from Siena. The farmhouse has been renovated to return it to its original splendour – you can look forward to traditional features like wood beams and terracotta tiles. Outside, there’s a pool to swim in, a lush garden, and a loggia with a barbecue, perfect for alfresco dining. *Access to this home is via a 300-metre dirt road. We recommend hiring a car to get the most out of your stay. There’s free parking here. *Your host can provide a cot and high chair for little ones. *There are stairs to climb at this home, so it may not be suitable for those with reduced mobility. There’s a twin bedroom on the ground floor. *While not every bedroom or bathroom has been photograph...More Details

Booked

Available

Radda in Chianti, House for rent

House • 6 People • 4

• 3

•

From

€

583 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 583 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Chianti Stone

You'll find this stone villa in the Chianti countryside. Radda and Castellina are both 5 kilometres away, so you'll be well-positioned to explore the area's vineyards and villages. Florence is also driveable in an hour if you have day trips in mind. That said, with a private pool and sun-kissed garden to enjoy back home, we don't blame you if you'd rather stay put. The villa itself is well-equipped, though the traditional style may not suit everyone. Two downstairs bedrooms open straight onto the garden, while the two upstairs have air conditioning and en-suite bathrooms. Rustic charm abounds indoors and out – think wooden beams, stone walls, and a covered terrace ideal for dining on Italian classics. *While this home can sleep up to eight people, the maximum occupancy is six guests. *Only the two upstairs bedrooms have air conditioning. All other rooms, including the lounge, have ceiling fans. *If you’re travelling with little ones, ...More Details

Booked

Available

Castellina in Chianti, Apartment for ren

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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Available

Greve in Chianti, House for rent

House • 20 People • 10

• 6

•

From

€

561 /night

Min Stay 7 nights

Greve in Chianti, Italy

€ 561 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

"Borgo Castagnoli", 14-room house 470 m2 on 2 levels. Wooden furniture furnishings: living/dining room with open-hearth fireplace, dining table, kitchen corner and satellite TV. Living/dining room with dining table and satellite TV. 1 room with 1 french bed (160 cm). 1 room with 2 beds (80 cm). Open kitchen (oven, dishwasher, 5 gas rings, freezer, electric coffee machine) with small dining table, open-hearth fireplace. Shower/WC, sep. WC. Upper floor: living/dining room with open-hearth fireplace, dining table and satellite TV. 5 rooms, each room with 1 french bed (160 cm). 3 rooms, each room with 2 beds (80 cm). Open kitchen (oven, dishwasher, 4 gas rings, freezer, electric coffee machine). Bath/WC, 4 showers/WC. Gas heating. Parquet floors. Terrace roofed. Facilities: washing machine, iron, baby cot for up to 2 year olds. Internet (WiFi, free). Parking (5 cars) at the house. Maximum 1 pet/ dog allowed. No internal connecting door betw...More Details

Booked

Available

Greve in Chianti, House for rent

House • 8 People • 4

• 4

•

From

€

561 /night

Min Stay 7 nights

Greve in Chianti, Italy

€ 561 /Night (minimum stay 7 nights)

Swimming Pool

Air Conditioning

WiFi

Credit Cards Accepted

8-room house 330 m2 on 3 levels. Spacious, stylish and romantic furnishings: entrance hall. Upper floor: open living room with open-hearth fireplace. Exit to the terrace. Large dining room with open-hearth fireplace. Small dining room. 3 double bedrooms, each room with air conditioning. 1 room with 2 beds (90 cm), air conditioning. Kitchen (oven, dishwasher, Gas stove, 5 gas rings, toaster, kettle, microwave, electric coffee machine, Capsules for coffee machine (Nespresso) extra) with open-hearth fireplace. Exit to the terrace. 2 baths/bidet/WC, shower/bidet/WC. 2nd upper floor: living room with panoramic window with TV (flat screen). Bath/shower/bidet/WC. Gas heating. Natural stone floors. Comfortable furnishings in the country house style. Large terrace 50 m2, terrace. Terrace furniture, deck chairs, box-room. Very beautiful panoramic view of the countryside. Facilities: washing machine, iron, mosquito net, children's high chair, baby...More Details

Booked

Available

Greve in Chianti, House for rent

House • 6 People • 3

• 3

•

From

€

524 /night

Min Stay 7 nights

Greve in Chianti, Italy

€ 524 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Credit Cards Accepted

"Casa 360", 4-room house 205 m2 on 2 levels, on the ground floor. Renovated in 2019, beautiful and cosy furnishings: large living/dining room with TV and air conditioning. Exit to the garden. 1 double bedroom with shower/WC and air conditioning. 1 double bedroom with shower/WC and air conditioning. Kitchenette (4 hot plates, oven, dishwasher, freezer). Upper floor: 1 double bedroom with shower/WC and air conditioning. Terrace furniture, barbecue. Very beautiful panoramic view of the countryside. Facilities: washing machine, children's high chair, baby cot for up to 2 year olds. Internet (WiFi, free). 1 pet/ dog allowed. IT048021B5JU359FTG Outside Description: Casa 360, located in the heart of Chianti Classico, is surrounded by the vineyards of the historic Savignola Paolina winery to which it belongs. Recently renovated in a modern style, it can accommodate up to six people. In the garden there is a swimming pool for private use. Agri...More Details

Booked

Available

Castellina in Chianti, Farmhouse for ren

Farmhouse • 14 People • 7

• 6

•

From

€

510 /night

Min Stay 7 nights

Castellina in Chianti, Italy

€ 510 /Night (minimum stay 7 nights)

Swimming Pool

Air Conditioning

WiFi

Credit Cards Accepted

"Cerretino + Tettoia", 10-room cottage 180 m2 on 2 levels. Spacious, renovated, tasteful and cosy furnishings: open living/dining room with dining table and satellite TV (flat screen), air conditioning. Living room with dining table and air conditioning. 2 double bedrooms, each room with air conditioning. Open living/dining room with dining table, kitchen corner and air conditioning. 1 room with 2 beds (80 cm, length 190 cm), air conditioning. Open kitchen (oven, dishwasher, 8 gas rings, toaster, kettle, microwave, electric coffee machine) with dining table. 2 showers/WC. Upper floor: 2 double bedrooms, each room with shower/WC and air conditioning. 1 double bedroom with air conditioning. 1 small double bedroom with sloping ceilings, without wardrobe with air conditioning. 2 showers/WC. Gas heating (extra), air-conditioning. Natural stone floors. Comfortable furnishings in the country house style. 3 terraces, patio. Terrace furniture, d...More Details

Booked

Available

Radda in Chianti, House for rent

House • 8 People • 3

• 3

•

From

€

477 /night

Min Stay 7 nights

Radda in Chianti, Italy

€ 477 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Credit Cards Accepted

"Villa del Poggio", 4-room house 95 m2 on 2 levels. Beautiful and tasteful furnishings: living/sleeping room with 1 double sofabed, open-hearth fireplace, satellite TV, radio, CD-player and DVD. Exit to the terrace. 1 room with 1 french bed (160 cm), shower/bidet/WC. Exit to the garden. 1 room with 2 beds and shower/WC. Exit to the garden. Open kitchen (oven, dishwasher, 5 gas rings, toaster, kettle, microwave, freezer, electric coffee machine) with dining table. Exit to the garden. Upper floor: 1 room with sloping ceilings with 1 french bed (160 cm). Shower/WC. Gas heating, air-conditioning. Comfortable furnishings in the country house style. 2 terraces, porch. Terrace furniture, barbecue, deck chairs, box-room. Beautiful view of the garden, the countryside and the forest. Facilities: washing machine, safe, iron, mosquito net, children's high chair, baby cot. Internet (WiFi, free). Please note: non-smokers only. Maximum 2 small pets/ d...More Details

Booked

Available

Radda in Chianti, House for rent

House • 6 People • 3

• 2

•

From

€

474 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 474 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Vineyard Sunset

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. *There's no air conditioning here, but fans are provided for guests' comfort. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *The swimming pool, open from May until mid-October, isn't fenced. Children will need to be supervised at all times. *There are steps to access this home. It may not be the best option for those with reduced mobility. *We recommend hiring a car to get the most out of ...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

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, 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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Available

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

Found 144 Chianti holiday homes for rent

Castellina in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Greve in Chianti, Italy

Greve in Chianti, Italy

Greve in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Chianti Property for rent