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Holiday Rentals with Pools in Radda in Chianti

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    Travellers to Radda in Chianti are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    37 Matching Rentals in Radda in ChiantiView all 66 rentals
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    Chianti Cashmere Vacation Rentals, Rural Tuscany1 / 40
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    10 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cornino Apartments is a typical tuscan villa composed by two separated apartments. It's situated in Volpaia, Radda in Chianti. It’s sorrounded by vineyards and it's the perfect accomodation for a group of friends or a big family. It's good until 20 people. On the ground floor there is a large...
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    53017, Volpaia, Radda in Chianti
    Condo/Apartment - 10 Bedrooms, 9 Bathrooms, Sleeps 20
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    Chianti Luxury Suite, Radda in Chianti - Siena1 / 20
    (22)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Mountain Views
    • Patio
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Central Heating
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    I can't recommend this beautiful place highly enough. Renovated with an amazing attention to detail, this feels like entering a loved home and a piece of local history. The...
    Reviewed 26 February 2018
    My wife and I recently stayed at the Chianti Luxury Suite. We fell in love with the location, the private garden and the pool overlooking the Italian forest. Every morning we...
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    About this property
    Chianti Luxury Suite is a secluded 100 sq. m. luxurious boutique accommodation that comfortably sleeps 2 adults. It is nestled in the heart of the most exclusive part of the Chianti Classico, on a hilltop just outside of Radda in Chianti. The 5 hectare estate boasts a beautiful Tuscan garden, with...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casale il Gualdo is an old stone house, completely independent, measuring 300 sq. m. and capable of holding up to 16 people with 8 double bedrooms and 5 bathrooms. The farmhouse, with an exclusive pool with Infinity edge, Wi-Fi, satellite TV and air conditioning, is perfect for groups of friends or...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 16
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    Fiorita1 / 26
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Central Heating
    • Washer
    • Grill
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2014
    The place was a charming old farmhouse but redone and quite comfortable for the 9 of us to stretch out in. Radda and Castellino were both about 10 minutes away.
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    About this property
    Typical country house in stone, 150 sq. m., with 4 double bedrooms and 3 bathrooms, holding up to 8 persons. The villa has a large garden with private swimming pool, an outdoor area for lunches with barbecue, internet and satellite TV. The property is ideal for families with children or for groups...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Shared Outdoor Pool (Unheated)
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ancient farm located in the heart of Chianti (Castellina in Chianti) near Siena, a few kilometers from Florence. The property is situated in a scenic position which gives onto wide views of the hills and valleys of the area and surrounded by the numerous olive groves. A small lake, created from the...
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Holiday House Le Selvole1 / 18
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Central Heating
    • Shared Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 November 2016
    We stayed here in Radda for a change from Volterra. This place has a private and gated entrance to the well kept grounds with ample parking. The host was very accommodating and...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Studio, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This farmhouse is situated in one of the most beautiful positions, right in the heart of Chianti Classico. From its secluded position, the windows frame a picture of the lovely Chianti countryside at its best. The interiors have been restored in an authentic Tuscan style and the living spaces all...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Central Heating
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    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ancient farm located in the heart of Chianti (Castellina in Chianti) near Siena, a few kilometers from Florence. The property is situated in a scenic position which gives onto wide views of the hills and valleys of the area and surrounded by the numerous olive groves. A small lake, created from the...
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    13 Bedrooms, 19 Bathrooms, Sleeps 50 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fantastic villa in the heart of the beautiful Chianti countryside, between Siena and Florence is surely one of the best places in the region to hold a large event. As well as lovely interiors it has beautiful grounds including a pool and chapel
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 13 Bedrooms, 19 Bathrooms, Sleeps 50
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Brief description Type of property: detached house Number of persons: 6 Floor space: 120 m² Room/s: 4 Bedroom/s: 3 Pool (available): private use Boat (not available): Pet (available): Pet allowed Sauna (not available): Next village/town: Center Radda in Chianti in approx. 2 km...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Outside Typical Tuscan stone farmhouse IT********.1 and annex IT********.3 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...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Gualdo Preludio1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Shared Outdoor Pool (Unheated)
    • Shared Garden
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ancient farm located in the heart of Chianti (Castellina in Chianti) near Siena, a few kilometers from Florence. The property is situated in a scenic position which gives onto wide views of the hills and valleys of the area and surrounded by the numerous olive groves. A small lake, created from the...
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ancient farm located in the heart of Chianti (Castellina in Chianti) near Siena, a few kilometers from Florence. The property is situated in a scenic position which gives onto wide views of the hills and valleys of the area and surrounded by the numerous olive groves. A small lake, created from the...
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Brief description Type of property: detached house Number of persons: 6-8 Floor space: 95 m² Room/s: 4 Bedroom/s: 3 Pool (available): private use Boat (not available): Pet (available): Pet allowed Sauna (not available): Next village/town: Center Radda in Chianti in approx. 2 km...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chianti, La Pruneta, Raffaello Apartment1 / 18
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Washer
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2017
    A lovely place in the heart of the Chianti region. Rebecca and her husband Massimo are the sweetest and super helpful providing everything you might need. The cottage is...
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    About this property
    A beautiful old farmhouse in the heart of Tuscany, 20 minutes from Radda in Chianti, set amongst olive trees and vines covering 6 hectares of land on slopes overlooking the Arno Valley. Raffaello is a beautifully restored one bedroom apartment with antique furniture, wooden-beamed ceilings,...
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    52022, Radda in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Washer
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Il Torrino is a beautiful country home, composed of a main house and an annex, sleeping 12 in its 6 double bedrooms with 6 bathrooms. The house, which has recently been restored maintaining beam ceilings and cotto floors, has internet connection and all the bedrooms have an en-suite marble...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    COSOLI CHARMING HISTORICAL VILLA IN CHIANTI1 / 17
    (1)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Mountain Views
    • Washer
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cosoli is a family house and the main residence of the owners. It is ideally located right in the middle of Chianti Classico, midway between Florence and Siena, allowing to experience the atmosphere of the surrounding small towns, like Greve, Castellina, Radda, Volpaia, Vertine, but in easy reach...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    L’Angolino is a renovated, pleasant country house with swimming pool which sleeps 6 with two double bedrooms, 1 twin-bedded room and two bathrooms. The house is located in a residential area close to Radda in Chianti, with all kinds of shops and therefore it is an ideal accommodation for a family...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those who love to be deep quite in the Chianti countryside, but with the advantage of a village at walking distance, Campassole is certainly the ideal property. The villa is an imposing stone-built farmhouse, ideally set in the gorgeous framework of Tuscan rolling hills, with enchanting views...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Central Heating
    • Shared Garden
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ancient farm located in the heart of Chianti (Castellina in Chianti) near Siena, a few kilometers from Florence. The property is situated in a scenic position which gives onto wide views of the hills and valleys of the area and surrounded by the numerous olive groves. A small lake, created from the...
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leccino is one of three houses on a premier biological extra virgin olive oil estate called 'Pornanino' , that sits on a panoramic hill in the Chianti Classico region of Tuscany in the heart of the Gallo Nero area between Radda, Castellina and Vagliagli. It's a self contained cosy barn completely...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Owner's description:Brief description Type of property: detached house Number of persons: 2-3 Floor space: 45 m² Room/s: 2 Bedroom/s: 1 Pool (available): private use Boat (not available): Pet (not available): No pets allowed Sauna (not available): Next village/town: Center Radda in Chianti in...
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    53017, Volpaia, Radda in Chianti
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.
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    53013, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Beautiful Farmhouse in the Chianti Near Town - Casa Radda1 / 28
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely farmhouse, located in the heart of the Chianti Classico just one kilometer from Radda, has beautiful views of the countryside which can be enjoyed both inside and outside of the villa. Radda is a wonderful Chianti town, with shops, restaurants and markets; it is only 1 km away from the...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dating from the 17th century, Villa Vistarenni suits those who want to spend some time in the countryside and yet be able to enjoy the beauty and comforts upon which the aristocratic Tuscan families modeled their houses. The original historical architecture has been preserved; add to that the...
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    53013, Radda in Chianti, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 13
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Brief description Type of property: detached house Number of persons: 8 Floor space: 250 m² Room/s: 5 Bedroom/s: 4 Pool (available): private use Boat (not available): Pet (available): Pet allowed Sauna (not available): Next village/town: Center Panzano in Chianti in approx. 5 km...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casavecchia is part of one of the most sought-after destinations in Chianti Region: Castello di Volpaia. The hamlet is one of the finest and most well-preserved Tuscan destinations as it maintains its original fortified medieval structure. This hamlet mostly belongs to one of the most renowned...
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    53017, Volpaia, Radda in Chianti
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
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    Pet friendly
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    Smoking allowed
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    53037, Radda in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large country house, entirely built in stone, in the heart of the Chianti hills. This is one of the most popular international tourist destinations which lovers of the Tuscan countryside all ask for. Everywhere there are vineyards which, in October, are tinted with numerous shades of red blending...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    La Pozza di Volpaia1 / 35
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2015
    La Pozza di Volpaia is a wonderful getaway in the little village of Volpaia in Tuscany, Italy (population 37). Its location is everything. You sit poolside, looking out over a...
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    About this property
    This property is located in the fortified medieval hamlet of Volpaia, in the Chianti Classico area, in a secluded position ensuring complete privacy. It is just a 300 metre walk to the centre of the hamlet, with two restaurants, one of which managed by the Castello di Volpaia farm, where it is...
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    Location Information
    53017, Volpaia, Radda in Chianti
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
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    Studio, 5 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This renovated stone farmhouse is located in the fortified medieval hamlet of Volpaia, considered by some, one of the best remaining examples of its kind. The farmhouse enjoys a secluded position within the hamlet, ensuring complete privacy. Located 300 meters from the farmhouse you will find two...
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    Location Information
    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa del Podestà has been obtained from the careful restoration of an ancient stone house and can host 6 people in 3 bedrooms and 3 bathrooms. The interiors have been restored in full respect of tradition but with the addition of such modern comforts as satellite TV and internet access, furthermore...
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    Location Information
    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Central Heating
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casale di Volpe is a stone country house of 250 square metres, composed of a main house and a guest house, sleeping 11 people in 5 double bedrooms, 1 single and 5 bathrooms. The restoration of this holiday home is an outstanding example of good taste and skilful use of the materials of the Tuscan...
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    Location Information
    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
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