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Castellina In Chianti Luxury Holiday Homes

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    Travellers to Castellina In Chianti are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    30 Matching Rentals in Castellina In ChiantiView all 203 rentals
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    Authentic 3 Bedroom Farmhouse1 / 30
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    CYPRESSES VILLA with private POOL1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Villa Patrignone - a beautiful large Tuscany Villa1 / 38
    (26)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Vrijstaande villa (1-8) met zwembad en pizzaoven.1 / 29
    (5)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Central Heating
    • Patio
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2016
    This house is really something. Conveniently located between Siena, Florence and Pisa I don't think you would find a finer spot in Tuscany. And the place itself: fantastic. You...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    15 Bedrooms, 15 Bathrooms, Sleeps 33 Quick View
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    • Balcony
    • Washer
    • Central Heating
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Podere Patrignone is a beautiful old 15th Century estate ('podere') which has been lovingly and tastefully restored. Patrignone is set on top of it's own hill reached by a long, winding private road that ends at Patrignone. It is set in 150 acres of forest, olives and vines, with uninterrupted 360...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 15 Bedrooms, 15 Bathrooms, Sleeps 33
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Grill
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Typical farmhouse with annexe, recently restructured and complete with every luxury, with a total area of 180 sq. m., holding up to 8 persons with 4 double bedrooms and 4 bathrooms. The private swimming pool is in a panoramic position surrounded by large outdoor areas which, together with a...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Washer
    • Central Heating
    • Balcony
    • DVD Player
    • Grill
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Feature: Property on a manor. natural stone house. Situation: rural, solitary, altitude 494 m, panoramic view. Access/parking: gravel road, approx. 2 km, winding. parking on the estate. Estate (private use): approx. 1.7 ha (whole estate 7 ha) , closed plot (fence, entrance gate), in a hillside,...
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    53011, Ricavo, Castellina In Chianti
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Washer
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casale il Poggino, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhouse which is divided into three apartments (for 14 people) communicating with each other from the outside and the annex (for 02 people) country house 'Casale Il Poggino', 400 m...
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    53011, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On request and to be paid for on location: domestic help (extra hours), cook. The guests can participate in a typical buffet dinner to taste the farm products that is organized every week (payment on location).. - Parking on the site - Pool open May - end September - Private outdoor swimming pool -...
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    53011, San Leonino, Castellina In Chianti
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
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    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large country house with stunning panoramic views. - Parking on the site - Pool open May - end September - Private outdoor swimming pool - Consumption costs incl. - Air conditioning cold/hot - Bedlinen incl towels (included) - Cot: 1 - Child's chair: 1 - Pets: 1 Costs overview: Mandatory services...
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    53011, San Leonino, Castellina In Chianti
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Villa Patrignone 7 bedroom Tuscany villa with pool1 / 24
    (2)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Grill
    • Balcony
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2014
    Our hosts, Simon and Verity, were marvels of hosting. They made sure we were comfortable and knew the ins and outs. They were hospitable without being intrusive. A true skill...
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    About this property
    Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has most of its original...
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    53011 SI, Castellina In Chianti, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Villa Delle Upupe 81 / 59
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2017
    We stayed in the villa for 15 days and enjoyed every moment. The house is spacey, comfortable, clean and has a good atmosphereThe garden and pool are phenomenal, the views are...
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    About this property
    RECEPTIVE STRUCTURE. Villa delle Upupe is located approximately 2 km from the borgo of Castellina in Chianti, in the hilly green countryside between Siena and Florence in the heart of Chianti Classico, a beautiful region famous throughout the world for its picture-postcard views and for the...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in the heart of the magical Chianti Classico region, this wonderful 6 BD – 6 BA Villa dates back to the 15th century and is strategically located with a short distance from the lively village of Castellina in Chianti. Surrounded by an exceptionally beautiful landscape, the property is perfect...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large stone-built farmhouse (480 m2) completely restored farmhouse, situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti in a peaceful and panoramic position amidst the vineyards and gently rolling hills of Chianti Classico (350 m a.s.l.) between...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casale San Donatino is an old stone house, 480 sq. m., holding up to 12 persons with 6 double bedrooms and 3 bathrooms. The house has a splendid, panoramic, private swimming pool, WiFi and a barbecue. It is ideal for groups of friends or large families. Outdoors and Swimming Pool The farmhouse has...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Il Torrino1 / 8
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inside, the property is set over 3 floors. On the ground floor, there is an open plan living and dining area, a separate well equipped kitchen, bathroom and 2 double bedrooms. A spiral staircase leads guests up the watchtower to a pretty single bedroom. Another spiral staircase leads to a second...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The villa in Chianti (400 m2) was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful restoration project that brought the structure back to its original beauty, a country villa rental has been...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Farmhouse Rental in Chianti Area of Tuscany - Villa Adelina1 / 46
    (7)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Central Heating
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of the Chianti, this farmhouse is situated on a beautiful and renowned wine estate that offers more than the typical Tuscan experience. Not only are there panoramic views of the rolling hills covered with vineyards and olive groves, but there is also the perk of being able to...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: villa is a place that has been stopped in time and is steeped in history. The quaint yet large cottage style villa is a nostalgic palace immersed in beautiful Italian woods, vineyards and olive groves. Surrounding this magnificent villa that is located in the Chianti area is...
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    50028, Ricavo, Castellina In Chianti
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    11 Bedrooms, 8 Bathrooms, Sleeps 21 Quick View
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    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Pool will be open on: 26 Apr 2019 22:00:00 \r\nPool will be close on: 27 Sep 2019 22:00:00 \r\nInternet wi-fi. The Lilliano estate, an ancient fortified complex dating from the Middle Ages, extends over an area of around 460 hectares in a splendid, tranquil and panoramic...
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    Location Information
    53011, Castellina In Chianti, Province of Siena
    Condo/Apartment - 11 Bedrooms, 8 Bathrooms, Sleeps 21
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Pool will be open on: 26 Apr 2019 22:00:00 \r\nPool will be close on: 27 Sep 2019 22:00:00 \r\nCleaning is from Monday to Friday (also on Saturday for stays longer than 1 week). Internet wi-fi. Villa Belvedere is a large and attractive stone farmhouse, lying within the old...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Pool will be open on: 26 Apr 2019 22:00:00 \r\nPool will be close on: 27 Sep 2019 22:00:00 \r\nCleaning also on Saturday for stays longer than 1 week. Internet wi-fi. Villa Oratorio is a classic stone farmhouse going back to 1500. It started out as a chapel and in 1876...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Independent villa sleeps 8 + 2 (260 square meters) On the ground floor there is a large living room with a stone fireplace and a large dining table, with a few steps next to it, the kitchen with dishwasher, oven, microwave, fridge and freezer, a double bedroom with a large...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Parking
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historical 18th Century villa with outbuilding, on two floors, 340 sq. m. with 5 double bedrooms and 4 bathrooms capable of holding up to 10 persons. The villa has a large terraced and enclosed park with a private swimming pool, an outdoor eating area with stonework barbecue, Wi-Fi and satellite...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Grill
    • Patio
    • Central Heating
    • Housekeeping Included
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From 2017 for the months of May and June only we are offering the entire main building of Le Ripe which includes the Stalle, the Loggia and the Main house, where we live during the rest of the year. While guests stay in the main building your hosts will lodge in the nearby Fienile. This special...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    • Patio
    • Internet Access
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of the Chianti area, at just 25 minutes from Siena and 50 minutes from Florence, this newly restored villa, called Olivia, offers the best of everything you could wish for in a holiday in Tuscany. Dating back to the 17th century, the villa is set in a large estate beyond a narrow road...
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    Location Information
    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Farmhouse Rental in Chianti Area of Tuscany - Casa Luciana1 / 26
    (18)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2013
    I rented this villa for a week so that my we could share Italy with my kids, their spouses and their young children. We needed a place with adequate bedrooms and bathrooms. Casa...
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    About this property
    Located in the heart of the Chianti, this farmhouse is situated on a beautiful and renowned wine estate that offers more than the typical Tuscan experience. Not only are there panoramic views of the rolling hills covered with vineyards and olive groves, but there is also the perk of being able to...
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    Location Information
    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    Studio, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large, stone-built farmhouse, dating back to the 16th century, is located on a well-known wine estate near Siena. The estate produces Chianti Classico wines. Ideal for a large family, this six bedroom farmhouse is built around an internal courtyard and is fully equipped with modern amenities...
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    Location Information
    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bathrooms, Sleeps 12
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Parking
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Outside this property, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhouse which is divided into three apartments (for 14 people) communicating with each other from the outside and the annex (for 02 people) country house 'this...
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    53011, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedroom Countryside Villa with Expansive Views1 / 36
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2014
    I stayed with my family at this beautiful villa. The setting is lovely on a hilltop, set amongst an active farm of olive trees and many vines. It was very helpful to have Elvira...
    Reviewed 22 October 2013
    My husband & I were 2 of 10 friends that stayed at this beautiful villa for a week in September. Simonetta & her family welcomed us with open arms & wonderful cheese...
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    About this property
    This beautiful property belongs to the Campalli estate, a huge farm of 750 acres that produces Chianti Classico wine, and includes the Castle of Campalli.The 360° view from each point on the estate ranges over endless rolling hills, vineyards and olive groves. On a clear day it is possible to see...
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    Location Information
    53011, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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