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Gaiole in Chianti Smoking Friendly Vacation Rentals

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    Travelers to Gaiole in Chianti are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    36 Matching Rentals in Gaiole in ChiantiView all 218 rentals
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    Cottage with pool for 2 couples - Interesting promotions for September weeks..1 / 36
    (14)Very good
    2 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    Experience the 'Chiantishire' at villa LisiDor - September is at 25% OFF!1 / 70
    (13)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Chianti house, Florence, Jacuzzi, Tuscany up to 6p1 / 42
    (7)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    LA VACANZA NEL CUORE DEL CHIANTI1 / 21
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Children's Pool
    • Grill
    • Mountain Views
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    Pet friendly
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 4 Bathrooms, Sleeps 7
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    Exclusive and reserved in Chianti - Quercia1 / 104
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Shared Yard
    • Secure Parking
    • Hot Tub
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 2017
    Loved this quiet and authentic apartment, we had everything we needed, the location was a bit remote but directions to get there clear. Beautiful outdoor area, the highlight...
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    About this property
    On the highest point of a hill set among the mosaic of the vineyards, typical of the Chianti Classico area, in the heart of a medieval village, you'll find the Pieve Marsina. The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hilltop Poolside 2 Bedroom Villa in Chianti1 / 27
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Hot Tub
    • Internet Access
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    Pet friendly
    Kid friendly
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    Reviewed August 30, 2015
    We spent 15 days at la Pieve Marsina. The host Gabriele, the old-stone house on a hilltop, the swimming pool, and the countryside (we were surrounded by Chianti vineyard) were...
    Reviewed August 1, 2014
    With my husband and 2 daughters we had a great vacation in Tuscany.The oldest is 17 and the youngest is 13 year old. We had a split level appartement with authentic...
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    About this property
    On the highest point of a hill set among the mosaic of the vineyards, typical of the Chianti Classico area, in the heart of a medieval village, you'll find the Pieve Marsina The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    UNA VACANZA DA SOGNO1 / 14
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning, large apartment of 140 sqm for 8 people, located in the medieval castle, near the restaurant and the reception, at 200 meters from the swimming pool. It is on two floors. Entrance on the ground floor, large kitchen (oven, two fridges, toaster, kettle) with a lovely, old stone fireplace....
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Grill
    • Wi-Fi
    • Balcony
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large and comfortable apartment of 80 sqm for 5 people, located in the building near the swimming pool, at 200 meters from the restaurant and the reception. It is on the ground floor and consists of a living room with stone fireplace, a single sofa bed, Sat TV, a dining area and a kitchen corner...
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Washer
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very ancient farmhouse dating back to year 1000 making part of a typical and charming chianti classico wine producing area with olive trees and wooded hills in a prestigious location between Florence and Siena, near the capital ot ghe vintage bycicle contest Eroica, Gaiole in Chianti, with pool,...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Chianti villa with private pool - Poggione1 / 18
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    PODERE MONTELUCCI - GAIOLE IN CHIANTI1 / 62
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Patio
    • DVD Player
    • Grill
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2018
    This Villa Montelucci has been really nice located on a hill and with good weather you even will be able to see Siena. The Villa is very comfortable with spacy, clean bedrooms...
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    MONTELUCCI ESTATE…….WHERE EVEN NATURE RELAXES…………………… UNSPOILT NATURE THE AGRITURISMO MONTELUCCI, FROM THE LATIN “MONS LUCI” (SACRED WOODS FOR THE ANCIENT ROMANS) IS NESTLED IN AN ENCHANTED WOOD OF FIRS, HOLM OAKS AND OAKS AT AN ALTITUDE OF NEARLY 700M ABOVE SEA LEVEL, OVERLOOKING THE HILLS OF THE...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large and comfortable apartment of 80 sqm for 5 people, located in the building near the swimming pool, at 200 meters from the restaurant and the reception. It is on the ground floor and consists of a living room with stone fireplace, a single sofa bed, Sat TV, a dining area and a kitchen corner...
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Secure Parking
    • Cable/satellite TV
    • Central Heating
    • Outdoor Dining Area
    • Wi-Fi
    • Private Yard
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Gaiole area, with its woods, vinyards and olivegroves, can be discovered on foot, on horseback, by bike or any other means of transport you prefer.The tourist information office in Gaiole will supply you with detailed route descriptions and maps, wich will guide you along well signposted paths...
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    53100, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Parking
    • Central Heating
    • Balcony
    • Porch
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Secure Parking
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Cable/satellite TV
    • Shared Yard
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    • Grill
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stone built property is located in a very secluded and panoramic location in the heart of Chianti Classico, 5 km from the village of Gaiole in Chianti. Perfect for those who would like to explore this part of Tuscany as well as enjoying 'al fresco' dining in its comfortable covered terrace...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 70 sqm apartment for 4 people, located in the medieval castle at 200 meters from the swimming pool. It is on the first floor and consists of living room with fireplace, Sat-TV, kitchenette (oven, fridge, toaster, kettle) and dining area, one double bedroom, one twin bedroom, and one...
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Comfortable, romantic apartment of 55 sqm for 2, located in the building near the swimming pool, at 200 meters from the restaurant and the reception. It is on two floors: the ground floor consists of one double bedroom and one bathroom with shower, a staircase leads to the living room with Sat TV,...
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Casa Ciaccheri1 / 13
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside. Outside a portion of an equipped courtyard is available for the exclusive use of the guests...
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Terrace
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    • Grill
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy stunning views over the...
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    53013, Gaiole 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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    • Central Heating
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    Pet friendly
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    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence.<BR><BR>Moreover, you can go trekking in the beautiful trails and nature walks on foot or...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Central Heating
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    • Wi-Fi
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning large apartment of 80 sqm for 5 people is located in the medieval castle, near the restaurant and the reception, and at 200 meters from the swimming pool. On the ground floor, it consists of a living room with stone fireplace, a single sofa bed, Sat TV, a dining area and a kitchen...
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This very special property is located on the edge of Castello di San Donato in Perano (Chianti), a beautiful hamlet which has recently been restored to such a high standard that it was awarded by the International Property Awards 2006. Cavalcanti’s position allows the guests to enjoy unusual...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    52013, Gaiole in Chianti, Province of Siena
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
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    • Shared Outdoor Pool (Unheated)
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    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Hot Tub
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    Kid friendly
    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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