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    Found 144 Chianti holiday homes for rent

    House • 2 People • 1 1 pets pool wifi
    From
    452 /night
    Min Stay 1 night

    Radda in Chianti, Italy 

    € 452 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Tuscan Cottage


    This beautifully restored and furnished Tuscan home is the true epitome of an Italian cottage done right. Right in the heart of the Chianti countryside, with the iconically distinctive cypress trees all around, this is the perfect haven for honeymooners looking for a romantic getaway or a solo tripper after a comfortable home close to Florence. The private pool is perfect for a refreshing dip, while the shaded dining areas invite you to savour leisurely meals alfresco. With its blend of traditional features and elegant touches, this home provides a romantic and restful escape. *Due to this home's location, we recommend hiring a car to get the most out of your stay. There is private onsite parking available. Please be aware that the approach road is unpaved and uneven, so a high clearance vehicle is recommended. *This home has two storeys, so it may not be suitable for those with reduced mobility. *The pool is only available for use fr...More Details


    • Booked Available
    House • 8 People • 4 3 pets pool wifi
    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
    Farmhouse • 14 People • 7 5 pets pool wifi
    From
    436 /night
    Min Stay 7 nights

    Radda in Chianti, Italy 

    € 436 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    9-room house 235 m2 on 2 levels. Rustic and cosy furnishings: living/dining room with satellite TV. Exit to the loggia. Living/dining room with open-hearth fireplace and satellite TV. Exit to the terrace. 1 double bedroom with shower/bidet/WC. 1 double bedroom with shower/bidet/WC. Kitchen (4 hot plates, oven, microwave, freezer, electric coffee machine). Upper floor: 1 double bedroom with shower/bidet/WC. 1 room with 2 beds. 1 double bedroom with shower/bidet/WC. 1 double bedroom. 1 double bedroom. Shower/bidet/WC. Facilities: washing machine. Internet (WiFi, free). 1 pet/ dog allowed. No internal connecting door between the separated properties. Only the annex is equipped with heating. IT052023B5JQ8ODLDB Outside Description: The Le Bonatte farm located in the heart of the Chianti Classico is made up of two real estate units (the farmhouse and the annex). The farmhouse, which can accommodate up to ten people, is not equipped with hea...More Details


    • Booked Available
    Cottage • 12 People • 6 6 pool wifi
    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
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    House • 10 People • 5 3 pets pool wifi
    From
    404 /night
    Min Stay 7 nights

    Greve in Chianti, Italy 

    € 404 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    "Villa Castagnoli", 7-room villa 250 m2 on 2 levels. Comfortable and wooden furniture furnishings: living/dining room with open-hearth fireplace, dining table and satellite TV (flat screen). Exit to the garden. Open kitchen (oven, dishwasher, 5 gas rings, freezer, electric coffee machine) with open-hearth fireplace. Sep. WC. Upper floor: 3 rooms, each room with 1 french bed (160 cm). 2 rooms, each room with 2 beds (80 cm). Bath/WC, 2 showers/WC. Gas heating. Parquet floors. Terrace roofed. View of the valley and the garden. Facilities: washing machine, iron, baby cot for up to 2 year olds. Internet (WiFi, free). Parking (4 cars) at the house. Please note: non-smokers only. Maximum 1 pet/ dog allowed. No mandatory extra charges to be paid on-site except for local tax. IT048021B49F5V68X8 Outside Description: Manor house "Castagnoli", 650 m ., surrounded by fields and vineyards. 12 km from the centre of Greve in Chianti, 2 km from t...More Details


    • Booked Available
    House • 6 People • 3 2
    From
    403 /night
    Min Stay 1 night

    Castellina in Chianti, Italy 

    € 403 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Dreaming of Chianti


    After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyone’s taste, but there’s no denying the beauty of the outdoor space. And, where better to cool off in the Tuscan heat, than the private pool? If you’re not dining alfresco and soaking up the countryside views, take the short drive to Quercegrossa for some authentic Italian food with the locals. *The owners live next door to the villa and have a dog and a cat, and there's an apartment that they occasionally use for family and guests. The apartment doesn't overlook the villa – it overlooks the pool slightly from a distance – they don't use the swimming pool and won't disturb you during your stay. *There's no air conditioning here. *The swimming pool, open between May and September weather permitting, isn't fenced. Children must be supervise...More Details


    • Booked Available
    Farmhouse • 12 People • 6 6
    From
    400 /night
    Min Stay 7 nights

    Castellina in Chianti, Italy 

    € 400 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    9-room semi-detached house 267 m2 on 2 levels, on the ground floor. Renovated, tasteful and cosy furnishings: living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the garden. 1 double bedroom. Exit to the garden. Living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the garden. 1 double bedroom. Exit to the garden. Living/dining room with open-hearth fireplace, dining table and satellite TV. Exit to the garden. 2 double bedrooms. Exit to the garden. Kitchenette (4 hot plates, mini-oven, electric coffee machine). 4 showers/bidet/WC. Upper floor: 1 large double bedroom. 1 double bedroom. Shower/WC, shower/bidet/WC. Large terrace, garden. Terrace furniture, barbecue. Facilities: Internet (WiFi, extra). Suitable for families. 2 pets/ dogs allowed. No internal connecting door between the separated properties. IT052005B42PTXEB5T Outside Description: Podere Gioia consists of tw...More Details


    • Booked Available
    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


    • Booked Available
    House • 12 People • 6 5
    From
    388 /night
    Min Stay 7 nights

    Greve in Chianti, Italy 

    € 388 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    "Il Poggio", 8-room semi-detached house 160 m2 on 2 levels, on the upper ground floor. Rustic and tasteful furnishings: living/dining room with open-hearth fireplace and satellite TV. 1 room with 2 beds. 1 double bedroom. Open gallery, ceiling height 100 - 190 cm with 2 beds. Living/dining room with open-hearth fireplace and satellite TV (flat screen). Exit to the loggia. 1 large double bedroom. 1 double bedroom. Kitchenette (4 hot plates, oven, dishwasher, kettle, freezer). 4 showers/bidet/WC. Heating. Upper floor: 1 double bedroom. Shower/bidet/WC. Garden. Terrace furniture. Panoramic view of the countryside. Facilities: washing machine. Internet (WiFi). 1 pet/ dog allowed. No internal connecting door between the separated properties. IT048021C2KGT7DHNB Outside Description: Torsoli 4 km from Lucolena: Il Poggio is a beautiful farmhouse divided into three residential units. Our proposal includes the possibility of booking, for a sing...More Details


    • Booked Available
    Apartment • 3 People • 2 1
    From
    382 /night
    Min Stay 1 night

    Castellina in Chianti, Italy 

    € 382 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Cheers to Chianti


    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. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this semi-detached home has a private entrance and garden...More Details


    • Booked Available
    Apartment • 16 People • 7 4
    From
    376 /night
    Min Stay 7 nights

    Gaiole in Chianti, Italy 

    € 376 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    "Il Gufo n°1", 9-room apartment 180 m2 on 2 levels on 1st floor. Comfortable and wooden furniture furnishings: living/dining room with open-hearth fireplace. Small living room with 1 double sofabed (160 cm), satellite TV. 1 double bedroom. Kitchenette (4 hot plates, dishwasher, microwave). Shower/WC. Upper floor: 2 double bedrooms with sloping ceilings. 4 small rooms with sloping ceilings, each room with 2 beds. Shower/WC, 2 showers/bidet/WC. Facilities: Internet (WiFi, free). 1 pet/ dog allowed. Shower with no shower plate. Outdoor area with table and chairs. IT052013B5JO6MFE6T Outside Description: Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, fields and it enjoys a wonderful view over the Chianti hills. It is a very quiet position, ideal for nature lovers to enjoy walks or bicycle runs in the surroundings area. Each apartment has its private outdoor area fenced...More Details


    • Booked Available
    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
    Apartment • 12 People • 6 3
    From
    371 /night
    Min Stay 7 nights

    Gaiole in Chianti, Italy 

    € 371 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    "Montechioccioli", 9-room house 210 m2 on 2 levels, on the ground floor. Object suitable for. Spacious, renovated, rustic and cosy furnishings: living/dining room with open-hearth fireplace, dining table and satellite TV. Living/dining room with open-hearth fireplace, dining table and satellite TV. Living/dining room with open-hearth fireplace, dining table and satellite TV. Kitchenette (oven, dishwasher, 4 gas rings, microwave, electric coffee machine). 3 sep. WC's. Upper floor: 3 double bedrooms. Exit to the balcony. 3 rooms, each room with 2 beds (80 cm). 3 showers/bidet/WC. Gas heating (extra). Natural stone floors. 3 balconies, 3 terraces. Terrace furniture, barbecue, deck chairs. Beautiful panoramic view of the countryside. Facilities: washing machine, children's high chair, baby cot for up to 2 year olds. Internet (WiFi, free). Parking (6 cars). E-charging station. Please note: suitable for families. Non-smokers only. 1 small pet...More Details


    • Booked Available
    Farmhouse • 10 People • 5 3
    From
    343 /night
    Min Stay 7 nights

    Radda in Chianti, Italy 

    € 343 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    6-room semi-detached house 180 m2 on 2 levels. Rustic and cosy furnishings: living/dining room with satellite TV. Exit to the loggia. Kitchen (4 hot plates, oven, microwave, freezer, electric coffee machine). Upper floor: 1 double bedroom with shower/bidet/WC. 1 room with 2 beds. 1 double bedroom with shower/bidet/WC. 1 double bedroom. 1 double bedroom. Shower/bidet/WC. Facilities: Internet (WiFi, free). 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. IT052023B5JQ8ODLDB Outside Description: Typical Tuscan stone farmhouse and annex 50 m away, situated in the heart of Chianti Classico. The house is attached to the owner's house on 1 side only. The heating is not available in the property. Set in the grounds of the farming estate of 24 ha. Private angling lake, 500 m. The original construction has been retained ...More Details


    • Booked Available
    Apartment • 5 People • 2 1
    From
    342 /night
    Min Stay 1 night

    Castellina in Chianti, Italy 

    € 342 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Grape Juice


    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. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this semi-detached home has a private entrance and gardens. *The shared pool is for seasonal use from May to Oc...More Details


    • Booked Available
    Apartment • 4 People • 2 2
    From
    337 /night
    Min Stay 1 night

    Castellina in Chianti, Italy 

    € 337 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Chianti Rosemary


    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. *Due to the unpaved, uneven access roads and uphill segments, a high clearance vehicle is recommended, and the roads may be better suited to experienced drivers. *This home is part of a collection of eight cottages and apartments within communal grounds. The swimming pool and parking area are shared, but this...More Details


    • Booked Available
    House • 6 People • 3 3
    From
    333 /night
    Min Stay 1 night

    Radda in Chianti, Italy 

    € 333 /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Beyond the Hills


    Situated in the heart of Chianti, this stone farmhouse is in a great spot for visiting some of the region’s many vineyards. Whether you’re admiring the countryside views from the wraparound terrace, cooling off in the private pool, or firing up the pizza oven, it’ll be easy to kick back and relax here. While the decor seems a little dated in places, the home boasts lots of traditional Tuscan touches, like terracotta tiled floors and beamed ceilings. Location-wise, you’re near the market town of Radda, and ever-popular Florence and Siena are just a day trip away. *Your host can provide a cot and high chair for free. You'll need to request them in advance. *The swimming pool is available for use between May and September. The pool isn't fenced so children will need to be supervised at all times. *Two well-behaved dogs, weighing up to 30kg each, are welcome to accompany you. *The twin bedroom can be configured as a double if required –...More Details


    • Booked Available
    Apartment • 6 People • 3 3
    From
    325 /night
    Min Stay 7 nights

    Greve in Chianti, Italy 

    € 325 /Night (minimum stay 7 nights)
  • Air Conditioning
    WiFi
    Credit Cards Accepted

    "Casa Paolina", 4-room apartment 120 m2 on 2 levels on 1st floor. Renovated in 2023, comfortable and cosy furnishings: entrance hall. Upper floor: living/dining room with air conditioning. Exit to the terrace. 1 double bedroom with shower/WC and air conditioning. 1 double bedroom with air conditioning. 1 double bedroom with shower/WC and air conditioning. Kitchenette (oven, 4 induction hot plates, freezer). Shower/WC. Large terrace 30 m2. Facilities: children's high chair, baby cot for up to 2 year olds. Internet (WiFi, free). IT048021C2ALT5RL7A Outside Description: The Casa Paolina apartment is located in the main building of the historic Savignola Paolina winery to which it belongs. Agriturismo on a vinyard "Casa Paolina", renovated in 2023. 3 km from the centre of Greve in Chianti, 35 km from the centre of Firenze, 46 km from the centre of Siena, in a sunny, elevated position on a slope, in the countryside. In the complex: receptio...More Details


    • Booked Available
    Cottage • 4 People • 2 1
    From
    315 /night
    Min Stay 1 night

    Castellina in Chianti, Italy 

    € 315 /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    Picturesque Embrace


    Whether you're visiting Chianti for the peace, the nature, the hiking trails or the vineyards, this attractive two-storey stone house is the ideal spot for settling down. With panoramic views of the sprawling hilly countryside, you could easily spend your days out on the private terrace, enjoying a paperback or sampling some local wines. Inside, you'll find everything you need for a comfy stay, including a pleasantly large kitchen and dining area below two bright, high-ceilinged bedrooms. Should you wish to venture beyond the grounds, popular towns like Castellina in Chianti are easily accessible by car, while the storied city of Florence can be reached in under an hour. *This home has a private well, which can be used during summer in the event of water shortages. *Due to this home's location, we recommend hiring a car to get the most out of your stay. *There’s free parking on the driveway here. Air Conditioning Barbeque Carbon M...More Details


    • Booked Available
    Farmhouse • 6 People • 2 1
    From
    300 /night
    Min Stay 7 nights

    Castellina in Chianti, Italy 

    € 300 /Night (minimum stay 7 nights)
  • Swimming Pool
    Air Conditioning
    WiFi
    Credit Cards Accepted

    4-room house 120 m2 on 2 levels, on the ground floor. Renovated in 2023, comfortable and cosy furnishings: living/dining room with open-hearth fireplace, satellite TV and air conditioning. Exit to the garden. Open gallery with 1 double bed and air conditioning. Kitchenette (4 hot plates, oven, dishwasher, freezer). Shower/bidet/WC. Upper floor: living/dining room with 1 double sofabed, open-hearth fireplace and satellite TV. 1 double bedroom with air conditioning. Exit to the garden. Kitchenette (4 hot plates, oven, dishwasher, toaster, kettle, microwave, freezer). Terrace furniture, barbecue. Panoramic view of the countryside. Facilities: washing machine, iron, children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). IT052005C2P4EUFYD7 Outside Description: Pretty stone farmhouse. The property, made up of two connected units, is immersed in the countryside in the heart of Chianti, an ideal area for vis...More Details


    • Booked Available
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