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Luxury Rentals in Gaiole in Chianti, Italy

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    Travelers to Gaiole in Chianti are booking August dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $3,756
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    1 / 12
    5 Bedrooms / 5 Bathrooms / Sleeps 18
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    $3,200
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    $2,175
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    7 Bedrooms / 7 Bathrooms / Sleeps 13
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    $1,457
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    1 / 19
    5 of 5 stars (1) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    Amenities & Details
    • Grill
    • Stereo System
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This beautiful, rustic villa is built on the side of a hill and surrounded by vineyards and woods. The villa is at the heart of an agricultural estate that produces organic wine and extra virgin olive oil. Good food, wine and relaxation await you in the heart of Tuscany. The stone building is set... View all property information
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    06018, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed July 6, 2013
    The villa is set within a delightful vineyard, with magnificent views over surrounding countryside and hills in all directions. The villa itself is fantastic - well equipped...
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    $1,326
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    1 / 26
    7 Bedrooms / 7 Bathrooms / Sleeps 13
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    • Private Outdoor...
    • Private Tennis Court
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
     Exterior Up a winding road through the trees you will find this exclusive villa atop a hill amidst 250 acres of farmland- cultivated fields, forests, olive groves and extensive vineyards. The main road to reach all landmarks of cultural and historical interest is just a stone´s throw away,... View all property information
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    53013, Gaiole in Chianti, Province of Siena
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    $1,326
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    1 / 31
    7 Bedrooms / 7 Bathrooms / Sleeps 14
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    Amenities & Details
    • Central Heating
    • Private Outdoor...
    • Private Tennis Court
    • Internet Access
    • Satellite TV
    • Stereo System
    • Mountain Views
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Charming Villa in Chianti with private pool, tennis court, concierge service, wi-fi and garden with stunning view on Tuscan hills. The villa can be rented up to 14 guest (Main Villa); in alternative up to 22 guest ( Main Villa plus apartment); For weddings, events and bigger groups up to 34... View all property information
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    53013, Gaiole in Chianti, Province of Siena
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    $1,326
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    1 / 19
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Grill
    • TV
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located in Chianti, near Siena and Florence, Tuscany, Italy, Casale Le Pratola has a commanding and private hilltop position, with 360 degree panoramic views of the surrounding Tuscan countryside. Casale Le Pratola is set in 2 hectares of secluded gardens filled with vines, olives, cypress trees,... View all property information
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    53013, Gaiole in Chianti, Province of Siena
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    $1,223
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    1 / 20
    5 Bedrooms / 6 Bathrooms / Sleeps 12
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    • Private Outdoor...
    • Stereo System
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Villa Stefano dates back to the 10th century and was originally a traditional stone water mill. The villa was recently renovated and great care was taken to ensure this was done sympathetically, respecting the historical structure of the building. Whilst the property has all the comforts of a... View all property information
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    01020, Gaiole in Chianti, Province of Siena
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    $8,341
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    1 / 46
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ExteriorsThis exclusive and luxurious villa in Chianti is a very short distance away from other Tuscan cities, such as Florence and Siena. Chianti has always been very famous for its exquisite wine. But apart from that, it holds many more experiences, ruled by ancient traditions and gastronomic... View all property information
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    53013, Gaiole in Chianti, Province of Siena
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    $1,096
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    1 / 37
    5 of 5 stars (15) Excellent
    5 Bedrooms / 5 Bathrooms / Sleeps 13
    Overview Reviews (15) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Housekeeping...
    • Game Room
    • Ping Pong Table
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Forbes Magazine voted Gaiole in Chianti Number 1 in its list of Europe's Most Idyllic Places to Live. Le Pratola is situated in the heart of Gaiole & has breathtaking 360 degree views. Watch our new video (shown after photos). With heated pool and at 6458 sq ft Le Pratola has 5 air conditioned... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed June 11, 2015
    Le Pratola (also called Villa Senese on some websites such as LaCure) is an amazing home on top of a private secuded hillside in Chianti. We recently stayed there for a week for...
    5 of 5 stars Reviewed June 9, 2015
    If you are looking to rent a gorgeous villa in Tuscany look no further, you’ve found the right place…. Le Pratola is a lovely property with a spectacular view of the Chianti hills...
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    From
    $6,606
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    1 / 40
    7 Bedrooms / 7 Bathrooms / Sleeps 18
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern design with original... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    From
    $6,076
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    1 / 28
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    From
    $5,600
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    1 / 34
    4 of 5 stars (1) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    Amenities & Details
    • Hairdryer
    • Private Outdoor...
    • Stove
    • Grill
    • Washer
    • Dishwasher
    • Central Heating
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This restored farmhouse is in the heart of the Chianti Classico. Really, that’s all you need to know! But this property would be an excellent choice even if it weren’t located in one of the most desirable vacation destinations in all of Italy. With a private pool, a lovely yard, and classically... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena
    From
    $773
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    1 / 16
    5 of 5 stars (1) Excellent
    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    Location Information
    Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed June 18, 2014
    This is a wonderful villa for spending some days enjoying the real Italian life. Children enjoyed the pool, we relaxed and had grest food and wine. A neat garden surrounds the...
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    $762
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    1 / 16
    7 Bedrooms / 5 Bathrooms / Sleeps 13
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    Amenities & Details
    • Satellite TV
    • Stereo System
    • Washer
    • Fireplace
    • DVD Player
    • Internet Access
    • Central Heating
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve, and the many fortified... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena
    From
    $5,148
    Per Week
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    1 / 17
    7 Bedrooms / 5 Bathrooms / Sleeps 18
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    Amenities & Details
    • Satellite TV
    • Fireplace
    • Central Heating
    • Ping Pong Table
    • Private Outdoor...
    • Staffed Property
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern design with original Tuscan... View all property information
    Make Inquiry
    Location Information
    Gaiole in Chianti, Province of Siena
    From
    $644
    Per Night
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    1 / 45
    11 Bedrooms / 11 Bathrooms / Sleeps 22
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    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Parking
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful Renaissance farmhouse built round a rustic characteristic threshing-floor in a fine panoramic position over Meleto Castle and the medieval village of Vertine. It has been recently fully restored and transformed into a prestigious villa with 4 apartments with every comfort. The furnishing... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    From
    $644
    Per Night
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    1 / 45
    11 Bedrooms / 11 Bathrooms / Sleeps 22
    Overview Make Inquiry
    Amenities & Details
    • Parking
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful Renaissance farmhouse built round a rustic characteristic threshing-floor in a fine panoramic position over Meleto Castle and the medieval village of Vertine. It has been recently fully restored and transformed into a prestigious villa with 4 apartments with every comfort. The furnishing... View all property information
    Make Inquiry
    Location Information
    Gaiole in Chianti, Province of Siena
    From
    $566
    Per Night
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    1 / 26
    12 Bedrooms / 11 Bathrooms / Sleeps 24
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Dryer
    • Private Outdoor...
    • Patio
    • Washer
    • Air Conditioning
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Superbly situated on a tranquil and panoramic hill in the Chianti region, in the heart of Tuscany, equidistant to Florence, Arezzo and Siena, this beautifully impressive Villa sits within an extensive landed estate. The villa is within walking distance to a typical Chianti village. A very well... View all property information
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    Location Information
    52022, Gaiole in Chianti, Province of Siena
    From
    $558
    Per Night
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    1 / 12
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Grill
    • Refrigerator
    • Washer
    • Central Heating
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    About this property
    Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from the town of Gaiole in Chianti. This villa, nestling deep in quiet position among vineyards and woods, offers full privacy and is the ideal place for those who seek a relaxing stay... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
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    From
    $558
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    1 / 46
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Private Outdoor...
    • Washer
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful independent villa with private pool situated in the heart of the Chianti region, a short distance away from the town of Gaiole in Chianti. This villa, nestling deep in quiet position among vineyards and woods, offers full privacy and is the ideal place for those who seek a relaxing stay... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    From
    $552
    Per Night
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    1 / 23
    5 of 5 stars (1) Excellent
    5 Bedrooms / 1 Bathroom / Sleeps 13
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Fireplace
    • Shared Outdoor Pool...
    • DVD Player
    • Internet Access
    • Parking
    • Central Heating
    • Refrigerator
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Il Mulinaccio is located between Radda in Chianti (7km) and Gaiole in Chianti (3km) on the SP2 road, 1.5km from the junction with the SS408 road from Montevarchi to Siena. The property is on a tar road, which those familiar with unpaved access will appreciate. There are two dwellings at Il... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed June 23, 2015
    This was an absolutely incredible holiday. It was a combination of the location, the house, the people I was with, the food and most definitely the hosts. Firstly the location...
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    $552
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ExteriorsVilla Gaiole is an authentic Sienese-style retreat with total privacy and comfort. Located in a natural environment of absolute privacy Villa Gaiole has recently  been remodeled and elegantly furnished. All rooms and bedrooms are air conditioned to allow all guests to choose their own... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    From
    $552
    Per Night
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    1 / 24
    6 Bedrooms / 7 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Game Room
    • Fireplace
    • Horse Riding Nearby
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A dive into an ancient culture in the heart of Tuscany, the Chianti Classico. Il Castello Medievale is situated in a medieval hamlet, constructed of white stone, built around 1000AD, surrounded by forests and olive groves, immersed in a magical atmosphere of tranquility. The Relais has five... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    From
    $3,756
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    1 / 12
    5 of 5 stars (1) Excellent
    5 Bedrooms / 5 Bathrooms / Sleeps 18
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Horse Riding Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    On entering the property, guests will find a welcoming living area, furnished with sofas around a traditional, focal fireplace. The kitchen is adjacent to this room. The kitchen is a typical Tuscan kitchen, well-equipped with plenty of pots and pans for those that enjoy cooking. A central table is... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed December 29, 2014
    I spent a week at Il Mulinaccio with friends this summer, and my only regret is that I spent too much time exploring the region and not enough just relaxing at the villa...
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    $3,723
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    1 / 40
    5 of 5 stars (1) Excellent
    7 Bedrooms / 7 Bathrooms / Sleeps 20
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Central Heating
    • Sauna
    • Game Room
    • Swingset
    • Mountain Views
    • Private Indoor Pool
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    New management summer 2015 In an ancient village of Chianti, immersed in nature and history, the charm of the past comes to life in an elegant seventeenth century villa, Villa degli Albizi. This exclusive home is elegant and a hut without time, full of charm and tranquillity; surrounded by woods,... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed June 11, 2015
    La villa è magnifica, elegantemente arredata e curata in tutti i suoi particolari. Ma gli spazi esterni (piscina e giardini) sono stati quelli più apprezzati, dai 9 bimbi...
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    $3,534
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    1 / 20
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Washer
    • Parking
    • Dishwasher
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This typical villa built in stone is located in the whereabouts of Gaiole in Chianti in the heart of Tuscany, on the green hills of the Chianti area, between Florence and Siena only a short distance away from the main tourist spots of Tuscany. The landscape is enchanting with vineyards clinging... View all property information
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    Location Information
    53013, Gaiole in Chianti, Province of Siena