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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.
    26 Matching Rentals in Radda in ChiantiView all 69 rentals
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    Chianti Cashmere Vacation Rentals, Rural Tuscany1 / 40
    (16)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Parking
    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    Suitability
    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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    Chianti, La Pruneta, Raffaello Apartment1 / 18
    (2)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 13 September 2018
    I stayed in this lovely place for some rest and recuperation. Beautiful scenery and lovely hills to walk in on the doorstep. Also an easy trip into Florence. Would strongly...
    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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    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • 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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    Fiorita1 / 26
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • Grill
    • Central Heating
    • Washer
    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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    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    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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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Washer
    • Grill
    • Central Heating
    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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    Holiday House Le Selvole1 / 18
    (5)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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    A paradise for families and couples!!!1 / 25
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2018
    This location invites you to a complete change of mind thanks to its beautiful view and really atypical disposition. The tower is wonderfully located with sun on the terrace...
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    About this property
    A view on a scenic wine and olive oil country. The ancient farmhouse of Augusto and Lele Vitali is an excellent base from which to explore the 'heart' of Tuscany. A few meters off the road to the village, the Torre, facing Radda, stands in an olive grove overlooking vineyards and a small lake....
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    13 Bedrooms, 19 Bathrooms, Sleeps 50 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    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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    Campassole1 / 28
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Grill
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2015
    My husband and I stayed at Campassole for two weeks in july and were completely recharged to take on the rest of the year. We arrived at one o'clock at night, still Margharita...
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    About this property
    This imposing stone-built farmhouse is situated only 1 km away from the lovely village of Radda in Chianti, yet it is in a quiet position on the rolling hills. This is a wonderful location, right in the heart of Chianti Classico, and only 35 kms from Siena. Campassole has been recently...
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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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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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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Wi-Fi
    • Central Heating
    • Balcony
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful farmhouse is located in a very quiet and secluded position on the Castello di Volpaia estate, where we have successfully been renting two other properties, La Pozza and Il Casetto for many years. The owners of the estate, with long experience in providing guest accommodations,...
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    53017, Volpaia, Radda in Chianti
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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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
    Suitability
    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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    Studio, 5 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • 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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    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bathrooms, Sleeps 11
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    Pozza Di Volpaia1 / 34
    (4)Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Grill
    • DVD Player
    • Balcony
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    The villa is imaculate and has every comfort. The location is fabulous with just a short stroll to the square where there are three wonderful places to eat and drink.We were on...
    Reviewed 4 October 2016
    The wonderful experience at La Pozza di Volpaia sets the standard for all Vacation in Tuscany. The gated villa is well appointed with a large kitchen and homey indoor and...
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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, 6 Bathrooms, Sleeps 11
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    Studio, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • 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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    5 bedroom Villa in Radda in Chianti, Tuscany, Italy : ref 50556031 / 20
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2018
    Stayed here for 2 weeks in the summer and had a great time. The house has everything you need and is stunning. Gioia was a great host and even better cook making some of her...
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    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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    Location Information
    53017, Radda in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Washer
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    • 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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    Il Paggino (Mimosa)1 / 13
    (1)Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Ancient property including 2 farmhouses, restored and divided into apartments in the heart of the Chianti Classico region, only 1 km from Radda in Chianti. The property is immersed in the typical Chianti landscape, with its hills and vineyards. From the pool...
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Wi-Fi
    • 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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Central Heating
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Ancient property including 2 farmhouses, restored and divided into apartments in the heart of the Chianti Classico region, only 1 km from Radda in Chianti. The property is immersed in the typical Chianti landscape, with its hills and vineyards. From the pool...
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    53017, Radda in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Crognole 61 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    Beautiful stone villa with all the ameneties situated in a picturesque vineyard owned by Castello di Albola. Lisa the housekeeper & her husband live in an anex to the main...
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    About this property
    RECEPTIVE STRUCTURE. Crognole stands on the top of a gentle 500 m-high hillslope, surrounded by the dream landscape of the unique hills of Chianti, with dense woods, olive trees and immense rows of vines that stretch to the horizon. It is a 16th century rural Tuscan house in stone which has been...
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    Location Information
    53017, Volpaia, Radda in Chianti
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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