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Smoking Allowed Holiday Rentals in Gaiole in Chianti

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    Travellers to Gaiole in Chianti are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    32 Matching Rentals in Gaiole in ChiantiView all 147 rentals
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    Secluded private hideaway in the middle of Chianti vineyards in silent position1 / 70
    (14)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    Exclusive and reserved in Chianti - Quercia1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Shared Garden
    • Secure Parking
    • Hot Tub
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Chianti house, Florence, Jacuzzi, Tuscany up to 6p1 / 42
    (7)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Parking
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2017
    A great place to stay. Very central in the Chianti region and very quiet and a little isolated which suited us very well indeed
    Reviewed 6 September 2016
    Our stay at the Villa was as expected. The location is isolated which we were looking for and most definitely in a beautiful and tranquil setting. Both Marcello and Sarah were...
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    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. Moreover, you can go trekking in the beautiful trails and nature walks on foot or by...
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    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Parking
    • Balcony
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Central Heating
    Suitability
    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
    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
    • Wi-Fi
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 7
    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
    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
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • 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
    UNA VACANZA DA SOGNO1 / 14
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Wi-Fi
    • Private Garden
    • Parking
    • DVD Player
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 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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    About this property
    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Chianti villa with private pool - Poggione1 / 18
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • Washer
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Casa Ciaccheri1 / 13
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Washer
    • Private Garden
    Suitability
    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
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Mountain Views
    • Central Heating
    Suitability
    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. Moreover, you can go trekking in the beautiful trails and nature walks on foot or by...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Studio, 5 Bathrooms, Sleeps 13 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 5 Bathrooms, Sleeps 13
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Mountain Views
    • Secure Parking
    • Cable/satellite TV
    • Central Heating
    • Outdoor Dining Area
    • Wi-Fi
    • Private Garden
    • 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Terrace
    • Washer
    • Grill
    • Private Garden
    Suitability
    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
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Cable/satellite TV
    • Shared Garden
    • Wi-Fi
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Parking
    • 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
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Sauna
    • Terrace
    • Private Garden
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Grill
    • Parking
    • 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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
    • Central Heating
    • Washer
    • Parking
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Hot Tub
    • Patio
    • 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Mountain Views
    • Private Garden
    • Wi-Fi
    • Washer
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
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    52013, Gaiole in Chianti, Province of Siena
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Hot Tub
    • Balcony
    • Washer
    • Private Garden
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Perfect romantic getaway in strategic location to main highlights of Chianti1 / 40
    (15)Very good
    2 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    As wonderful as expected - even better; in any way: Location, facilities, rooms...Perfect for trips on the countrysideVery kind ownersalso recommendable for families with...
    Reviewed 16 June 2017
    My family and i had a fantastic and absoultely relaxed holiday at PetrAlexa. You only hear the birds, when you wake up. You feel so free in the big garden and the Chianti Hills...
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    About this property
    Ciao from Petra &Alexa and thank you for stopping by! !!! Special offers just have started!: 20% on first two September weeks !!! Here is what our villa offers you for a memorable stay: *** First of all we will present you with an appetizing light dinner at your arrival, which you can enjoy any...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 5
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