Italy - Holiday Rentals in Chianti Italy

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

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Found 130 Chianti holiday homes for rent

San Polo-in-Chianti, House for rent

House • 4 People • 2

• 1

•

From

€

62 /night

Min Stay 7 nights

San Polo-in-Chianti, Italy

€ 62 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

"Capella", 3-room apartment 65 m2 on 2 levels. Practical and rustic furnishings: 1 double bedroom. Small kitchen (oven, 4 gas rings, toaster, kettle, microwave, electric coffee machine) with dining table. Upper floor: living room with satellite TV (flat screen). 1 double bedroom. Shower/bidet/WC. Heating (extra). Natural stone floors. Terrace. Terrace furniture, barbecue. Very beautiful panoramic view of Chianti. Facilities: children's high chair, baby cot for up to 2 year olds. Parking (1 car) at the house. Please note: suitable for families. Non-smokers only. Maximum 2 pets/ dogs allowed. Private entrance. IT048021B5HUDSPMZM Outside Description: Manor house "Panzalla", detached, surrounded by fields and vineyards. 6 apartments in the residence. Property composed of main house and outbuilding 4 km from the centre of San Polo in Chianti, 16 km from the centre of Impruneta, 23 km from the centre of Firenze, in a secluded, sunny, elevat...More Details

Booked

Available

San Polo-in-Chianti, House for rent

House • 8 People • 4

• 2

•

From

€

117 /night

Min Stay 7 nights

San Polo-in-Chianti, Italy

€ 117 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

"Fienile", 5-room semi-detached house 110 m2 on 2 levels. Spacious, rustic and antique furnishings: large living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the terrace. 2 double bedrooms. Small kitchen (2 hot plates, oven, dishwasher, 4 gas rings, toaster, kettle, microwave, electric coffee machine). Exit to the balcony. Shower/bidet/WC. Upper floor: 1 double bedroom. 1 room with 2 beds (80 cm). Shower/bidet/WC. Heating (extra). Natural stone floors. Balcony, large terrace 40 m2 partly roofed. Terrace furniture, balcony furniture, barbecue. Marvellous panoramic view of Chianti. Facilities: children's high chair, baby cot for up to 2 year olds, hair dryer. Parking (2 cars) at the house. Please note: suitable for families. Non-smokers only. Maximum 2 pets/ dogs allowed. Private entrance. IT048021B5HUDSPMZM Outside Description: Manor house "Panzalla", detached, surrounded by fields and vineyards. 6 apa...More Details

Booked

Available

San Polo-in-Chianti, Apartment for rent

Apartment • 8 People • 4

• 2

•

From

€

112 /night

Min Stay 7 nights

San Polo-in-Chianti, Italy

€ 112 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

"Rondini", 5-room apartment 100 m2, on the ground floor. Rustic and antique furnishings: living/dining room with open-hearth fireplace, dining table and satellite TV (flat screen). 4 double bedrooms. Open kitchen (oven, 4 gas rings, toaster, kettle, microwave, freezer, electric coffee machine). 2 showers/bidet/WC. Heating (extra). Natural stone floors. Terrace. Terrace furniture, barbecue. Very beautiful panoramic view of Chianti. Facilities: children's high chair, baby cot for up to 2 year olds. Parking (2 cars) at the house. Please note: suitable for families. Non-smokers only. Maximum 2 pets/ dogs allowed. Private entrance. IT048021B5HUDSPMZM Outside Description: Manor house "Panzalla", detached, surrounded by fields and vineyards. 6 apartments in the residence. Property composed of main house and outbuilding 4 km from the centre of San Polo in Chianti, 16 km from the centre of Impruneta, 23 km from the centre of Firenze, in a secl...More Details

Booked

Available

San Polo-in-Chianti, Apartment for rent

Apartment • 3 People • 1

• 1

•

From

€

46 /night

Min Stay 7 nights

San Polo-in-Chianti, Italy

€ 46 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

"Rustico", 2-room apartment 45 m2, on the ground floor. Object suitable for 2 adults + 1 child. Practical and rustic furnishings: living/sleeping room with 1 sofabed, open-hearth fireplace, dining table and satellite TV (flat screen). 1 double bedroom with shower/bidet/WC. Open kitchen (oven, 4 gas rings, kettle, freezer, electric coffee machine). Heating (extra). Natural stone floors. Terrace partly roofed, garden. Terrace furniture, barbecue. Marvellous panoramic view of Chianti. Facilities: children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). Parking (1 car) at the house. Please note: suitable for families. Non-smokers only. Maximum 2 pets/ dogs allowed. Private entrance. IT048021B5HUDSPMZM Outside Description: Manor house "Panzalla", detached, surrounded by fields and vineyards. 6 apartments in the residence. Property composed of main house and outbuilding 4 km from the centre of San Polo in Ch...More Details

Booked

Available

San Polo-in-Chianti, Cottage for rent

Cottage • 12 People • 6

• 6

•

From

€

415 /night

Min Stay 7 nights

San Polo-in-Chianti, Italy

€ 415 /Night (minimum stay 7 nights)

Swimming Pool

Air Conditioning

WiFi

Credit Cards Accepted

"Policleto", 9-room house 270 m2 on 3 levels. Spacious, partly renovated in 2023, comfortable and cosy furnishings: living/dining room with dining table, satellite TV, wood-burning stove and air conditioning. 2 double bedrooms, each room with shower/bidet/WC and air conditioning. Exit to the garden. 1 double bedroom with shower/bidet/WC and air conditioning. Kitchen (oven, dishwasher, 5 gas rings, toaster, kettle, microwave, freezer, electric coffee machine) with air conditioning. On the lower ground floor: (exterior staircase) living/dining room with kitchen corner. Exit to the garden. 1 double bedroom. Shower/bidet/WC. Upper floor: living/dining room with open-hearth fireplace, satellite TV and air conditioning. Open kitchen (oven, dishwasher, 4 gas rings, toaster). Shower/bidet/WC. 2nd upper floor: 2 double bedrooms, each room with air conditioning. Bath/shower/bidet/WC. Electric heating (extra), air-conditioning (extra). Parquet flo...More Details

Booked

Available

Strada-in-Chianti, Farmhouse for rent

Farmhouse • 8 People • 4

• 2

•

From

€

282 /night

Min Stay 7 nights

Strada-in-Chianti, Italy

€ 282 /Night (minimum stay 7 nights)

Swimming Pool

Pets Allowed

WiFi

Credit Cards Accepted

5-room house 110 m2 on 2 levels, on the ground floor. Comfortable and cosy furnishings: living/dining room with TV. 1 double bedroom. 1 double bedroom. 1 room with 2 beds. Kitchenette (4 hot plates, oven, dishwasher, toaster, kettle, microwave, freezer). Shower/bidet/WC. On the lower ground floor: 1 room, without window with 2 beds. Shower/WC. Terrace furniture, barbecue. Panoramic view of the countryside. Facilities: washing machine, children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). Suitable for families. 1 pet/ dog allowed. When there are less than the maximum number of guests staying at the property, not all of the bedrooms will be available for use. IT048021C2BABTABEJ Outside Description: Country house "Pilar", detached. 1 km from the centre of Strada in Chianti, 11 km from the centre of Greve in Chianti, 20 km from the centre of Firenze, in a quiet, sunny position on a slope, in the country...More Details

Booked

Available

Radda in Chianti, House for rent

House • 14 People • 7

• 6

•

From

€

1,411 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,411 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

An Italian Tale

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. *Please note this home is spread across a main house for six guests, a guest house for four guests and a pool house for four guests. *The housekeeper also lives on site but will respect total privacy. *If you're travelling with little ones, your host can provide a high chair for free upon request. *The swimming pool is only available from May to Septembe...More Details

Booked

Available

Radda in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

1,795 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 1,795 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Chianti Sunset

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? *The owners live on-site with their two friendly dogs, who you may see during your stay – please don't feed them. If you have severe allergies to pets, this home may not be best suited to you. *Three of the five bedrooms can be set up as super kings or twins on request. *Your host can provide a cot and high chair for free. You'll need t...More Details

Booked

Available

Radda in Chianti, House for rent

House • 12 People • 6

• 3

•

From

€

991 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 991 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Hilltop Dream

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. *Private parking is available for up to four cars. *This home is spread across two floors with stairs. Please also note bedrooms five and six have small double beds which are best suited to one adult or two children. *If you're travelling with little ones, your host can provide two cots and two high chairs for free. You'll need to request them in advance. *Please note the swimming pool is available for use from appr...More Details

Booked

Available

Radda in Chianti, House for rent

House • 10 People • 5

• 7

•

From

€

4,401 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 4,401 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Bloom

Breathtaking views, a private pool and an abundance of charm – this home welcomes you to enjoy it all from its privileged spot in Chianti. Outside, you’ll find everything you could need to sit back and savour the beauty of this special location. There’s a terrace for alfresco dining and a little playground for children. Inside, the wine cellar offers the perfect spot for wine tastings, while the steam room and gym cover all your wellness needs. Plus, a welcome dinner is provided, housekeeping is included and a private chef can be arranged on request. It’s also just a short drive to Radda in Chianti, while Sienna and Florence are also within easy reach. *Please note the housekeeper lives in a detached cottage on-site. *A complimentary welcome dinner and daily housekeeping are included in your stay along with daily laundry service and a twice weekly linen change. *The house is set across three floors with stairs. *If you’re travelling...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, House for rent

House • 8 People • 4

• 3

•

From

€

440 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 440 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

Like Sweetness

If you’re looking to experience the natural beauty of Chianti, this home delivers a charming solution. You’ll be welcomed by stunning views across the surrounding vineyards and there’s a private swimming pool for leisurely dips. Inside, the rooms are traditional, family-friendly and full of character. Your host is on hand to help organise sweet extras like private chefs, walking excursions and guided tours. Plus, it’s just a short drive to the nearest amenities while Siena is also within easy driving distance. *Please note the owners live next door with a dog and a cat – you may see them during your stay. *It is possible for the two single beds in the second bedroom to be arranged as a double bed on request. *Please note the swimming pool is open from May to September. *If you’re travelling with little ones, your host can provide a cot for free on request. *Private parking is available for up to three cars. *One well behaved dog is...More Details

Booked

Available

Radda in Chianti, House for rent

House • 6 People • 3

• 2

•

From

€

373 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 373 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Tuscan Vine

In the heart of Chianti Classico, this charming old stone villa offers a haven for wine enthusiasts. Surrounded by vineyards producing world-renowned wines, you can easily explore local wineries and historic towns like Radda. If you’re not sampling the local grapes, back home, you’ll find everything needed for a comfortable stay. Granted, there’s no air conditioning here, but with sun-dappled terraces, panoramic views and a private pool, you’re sure to be drawn outdoors anyway. Locally, a trip to Radda is a must, reached easily in under ten minutes in the car. *There's no air conditioning here. It could get a little hot during the summer. *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 September, isn't fenced. Children will need to be supervised at all times. *The twin bedroom can be set up as a double upon request. *We recommend hiring ...More Details

Booked

Available

Radda in Chianti, House for rent

House • 4 People • 3

• 2

•

From

€

299 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 299 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

WiFi

The Chianti Valley

Nestled amid the rolling hills and lush greenery of the Chianti countryside, this villa offers a tranquil escape to rural Italy. The stone house is as traditional as can be, with terracotta floors, wood-beamed ceilings, and arched doorways. Outside, you’ll find two terraces boasting wonderful views stretching over the valley to the nearby towns of Panzano and Radda – both great options for day trips. There’s also a swimming pool. Rustic and charming, this villa is an oasis in Chianti. *Access to this home is via an unpaved road – we recommend hiring a high-clearance vehicle. There’s free parking here. *The swimming pool is open from May to September. The homeowner and their family may use the pool when you’re not using it. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *There are stairs to climb at this home so it may not be suitable for those with reduced mobility. A twin bedroo...More Details

Booked

Available

Castellina in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

1,389 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,389 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Tuscan Moon

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. *Private parking is available for up to four cars here. *It is possible for the two single beds in bedroom one to be arranged as a double bed on request. *If you’re travelling with little ones, your host can provide a cot for free on request. *The fireplace in this hom...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

Castellina in Chianti, House for rent

House • 10 People • 5

• 4

•

From

€

1,154 /night

Min Stay 1 night

Castellina in Chianti, Italy

€ 1,154 /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Classic Moments

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. *Please note the main house is spread across three floors. You will also find two of the bedrooms are located in the adjacent annexe. *If you're travelling with little ones, your host can provide a free cot and high chair upon request. *All fireplaces in this home are ornamental. *The swimming pool is available for use from the last ...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 • 12 People • 6

• 5

•

From

€

5,309 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 5,309 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Stonehaven

The ultimate Tuscan getaway starts at this villa in Radda. Boasting a private pool, a gym and wellness area, and scenic views of the surrounding vineyards, you'll have everything you need here to unwind in style. We love the mix of contemporary design and historic elements like vaulted ceilings and stone archways. Even more, we adore the complimentary extras, such as tastings in the wine cellar, welcome dinners, and a continental breakfast buffet. When you're not relaxing at home, why not spend the day exploring? Castello di Brolio, Siena, and other Tuscan gems are all within driving distance. *While not every bedroom is photographed, expect the style and quality to be consistent with the rest of the home. The sixth bedroom may be in an annexe on the ground floor – please speak to your host for more information. *A welcome dinner on the first Monday night is included with your stay. You'll also have a complimentary wine tasting in the...More Details

Booked

Available

Radda in Chianti, House for rent

House • 10 People • 5

• 5

•

From

€

4,346 /night

Min Stay 1 night

Radda in Chianti, Italy

€ 4,346 /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Dream of Light

With a serene garden, beautiful views and a private pool, this home welcomes you to slow down and savour the magic of Italian living. There’s a wellness area with a Turkish bath and a sauna, as well as a wine cellar – making it easy to settle in and unwind. Upon arrival you’ll be treated to a light dinner and wine tasting, and your host is on hand to help organise a range of extras – including spa treatments and private chefs. You will need a car to get around here, but it’s just a short drive to the nearest shops and restaurants in Radda in Chianti, while Siena and San Gimignano are also within easy driving distance. *Daily housekeeping and breakfast are included in your stay (excluding Sunday). *A light welcome dinner is provided on Monday and wine tasting wine is offered on Wednesday. *Please note one of the bedrooms is located in the ground floor annexe. *The main house is set across three levels with a lift and stairs. *The hea...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

San Polo-in-Chianti, Italy

San Polo-in-Chianti, Italy

San Polo-in-Chianti, Italy

San Polo-in-Chianti, Italy

San Polo-in-Chianti, Italy

Strada-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

Radda in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Castellina in Chianti, Italy

Castellina in Chianti, Italy

Radda in Chianti, Italy

Radda in Chianti, Italy

Chianti Property for rent