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    Found 144 Chianti holiday homes for rent

    Apartment • 8 People • 3 1 pool
    From
    262 /night
    Min Stay 7 nights

    Castellina in Chianti, Italy 

    € 262 /Night (minimum stay 7 nights)
  • Swimming Pool
    Credit Cards Accepted

    "Tipologia Quadrilocale", 4-room apartment 98 m2 on 2 levels, on the ground floor. Comfortable and rustic furnishings: entrance hall. Living/dining room with open-hearth fireplace and TV. 1 room with 1 bed, 1 double bed and separate WC. Kitchenette (4 hot plates, dishwasher, microwave, freezer). Upper floor: 1 double bedroom. 1 room with 1 bed and 1 double bed. Bath/shower/bidet/WC. IT052022B5K2YANYJD Outside Description: The farm surrounded by olive groves and vineyards of Chianti. Each of 12 apartments are located in the main house and a former barn has its own outside area with a table on the terraces surrounding with the main building. The location is very central and ideal for trips to discover the natural and cultural beauties of the region large working farm "La Moraia", renovated. 14 km from the centre of Castellina in Chianti, 18 km from the centre of San Gimignano, 50 km from the centre of Firenze, in an elevated position, i...More Details


    • Booked Available
    Farmhouse • 10 People • 5 3 pets pool wifi
    From
    266 /night
    Min Stay 7 nights

    Gaiole in Chianti, Italy 

    € 266 /Night (minimum stay 7 nights)
  • Swimming Pool
    Pets Allowed
    WiFi
    Credit Cards Accepted

    "Lo Scoiattolo n° 10", 7-room house 115 m2 on 2 levels, on the ground floor. Wooden furniture furnishings: small lounge with 1 sofabed (160 cm), satellite TV. 01 double bedrooms. Kitchen (4 hot plates, oven) with dining table. Shower/bidet/WC. Upper floor: 2 rooms, each room with 2 beds. 2 double bedrooms. Shower/WC, shower/bidet/WC. Small patio. Facilities: Internet (WiFi, free). 1 pet/ dog allowed. Shower on the ground floor has no shower tray. 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 by hedges. A few kilometres away there are the Castello di Brolio (18 km), Meleto (14 km), Vertine (12 km) and Badi...More Details


    • Booked Available
    Farmhouse • 8 People • 4 2 pets pool wifi
    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
    House • 4 People • 3 2 pets pool wifi
    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
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    Farmhouse • 6 People • 2 1 pool wifi
    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
    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
    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
    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 • 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
    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
    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 • 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
    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 • 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
    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
    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
    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
    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 • 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
    House • 10 People • 5 3
    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
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