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Holiday Rentals with Pools in Gaiole in Chianti

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    Travellers to Gaiole in Chianti are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    $4,271
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    1 / 24
    5 of 5 stars (7) Excellent
    6 Bedrooms / 9 Bathrooms / Sleeps 12
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    $1,826
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    1 / 24
    4 of 5 stars (1) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    $963
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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    $856
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    1 / 12
    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Mountain Views
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    About this property
    Find Gaiole In Chianti Villas on FlipKey Our apartment is in Borgo di Gaiole, a small residential and holiday complex on the edge of the pretty village of Gaiole in Chianti in the heart of Tuscany in Italy. The Borgo has a lovely swimming pool and other amenities. It's just a few minutes walk... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    5 of 5 stars Reviewed 5 April 2015
    Lovely apartment in a really nice village. Great base for exploring. Easy walking distance to local village. Great nearby restaurants. Easy access to train for travel into...
    4 of 5 stars Reviewed 21 June 2014
    The apartment in the Borgo in Gaiole was lovely. It was well equipped with everything you need for a happy stay. From the village it was a steep walk uphill and then up steps...
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    $7,136
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    1 / 34
    4 of 5 stars (1) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Dishwasher
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
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    • 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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    Gaiole in Chianti, Province of Siena
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    $101
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    1 / 27
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dishwasher
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Appartamento Gaiole 15 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view of the surrounding hills.... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $563
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    1 / 19
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful Siena The apartment is on the... View all property information
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    Gaiole in Chianti, Province of Siena 53030
    5 of 5 stars Reviewed 22 March 2014
    We stayed several weeks in Franco's wonderful Casa Giardino. Unlike many one bedroom apartments, there is plenty of room to move here. The bedroom is large, the living room is...
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    $1,425
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    1 / 25
    4.5 of 5 stars (3) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    ' IL BACCHINO IN CHIANTI ' è una antica casa colonica rustica nel cuore della Toscana. Questo caratteristico casale in pietra del 1500, accuratamente ristrutturato, affonda le sue radici intorno all'XI secolo d.c.: le fondamenta murarie e le cantine della struttura risalgono a tale periodo... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013
    5 of 5 stars Reviewed 11 October 2014
    We had a wonderfull stay at Bacchino in Chianti. Anna and Andrea made us feel at home and were very kind and welcoming hosts. Poggio San Polo is a quiet location in the middle of...
    4 of 5 stars Reviewed 6 July 2014
    We received a warm welcome by the owners and shared stories over a complimentary local Chianti wine. The unit is situated in a 500 year old villa and although refurbished...
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    $143
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    1 / 13
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Ping Pong Table
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a french oak barrel (used as a... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $1,607
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    1 / 23
    4 of 5 stars (4) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Dishwasher
    • Grill
    • Private Outdoor...
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    In the heart of the Chianti Classico is where you'll find this house and it's location is not only to be appreciated because it's a short drive to town, but because it's set high on a hill with magnificent views outside of the surrounding vineyards and olive groves. This is definitely a place to... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013
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    $289
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    1 / 23
    5 of 5 stars (11) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Mountain Views
    • Ping Pong Table
    • Pool Table
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    A spacious well furnished three double bedroom, two bathroom apartment with an eight seating dining room and large lounge, just a few minutes stroll from the restaurants, cafes and wide range of services provided by Gaiole village. Outside, enjoy a game of boules in the tiered garden, or swing in... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013 SI
    5 of 5 stars Reviewed 10 November 2014
    Casacorvo Maggiore provides great accommodation for a group or family. The townhouse is well equipped and provides a lovely view over the town and the surrounding countryside. Our...
    5 of 5 stars Reviewed 3 February 2014
    Set within easy reach of many vineyards, beautiful Siena and only 50 minutes from Florence, my friends and I found the house to be perfectly equipped and finished to a high...
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    $4,150
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    1 / 60
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Villa Eracle is a bright and elegant three-story villa surrounded by vineyards and olive groves. It sleeps eight people. From Villa Eracle you will enjoy a fascinating view of the Chianti hills and of the vineyards. Villa Eracle is 240 square meters (2600 square feet). It features a private... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed 23 July 2013
    I went to Villa Eracle, Gaiole in Chianti the first week in July 2013 with my family. We spent 2 days running around Rome and it was a welcome relief to be in this tranquil...
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    $1,808
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    1 / 19
    5 of 5 stars (1) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
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    • Grill
    • Private Outdoor...
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • 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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    Location Information
    Gaiole in Chianti, Province of Siena 06018
    5 of 5 stars Reviewed 7 July 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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    $173
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    1 / 24
    5 of 5 stars (30) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (30) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Housekeeping...
    • Internet Access
    • Ping Pong Table
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Surrounded by the famous rolling hills covered with vineyards and olive groves, which give the name to some of the most prestigious Chianti wine is Borgo di Gaiole. The apartment is on the ground floor as you enter the Borgo, private and self contained around 60sq meters with the traditional... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    5 of 5 stars Reviewed 21 January 2015
    Our stay in this beautiful apartment couldn't have been better. The owners are true hosts, we couldn't have asked for more. The apartment is in a beautiful position at the top of...
    5 of 5 stars Reviewed 23 October 2014
    The experience could not have been better. The apartment is nearly new and was immaculate and well-maintained, the decor is welcoming, the bed is comfortable, the kitchen is well...
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    $264
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    1 / 19
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The imposing Meleto Castle is located in the heart of the Chianti Classico, near the ancient lines that marked the border between the Florentine and Senese Republic, in the centre of a large and well-known farm that extends for more than 1,000 ha. Despite the modifications that it has experienced... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013
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    $999
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    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximity to numerous wineries,... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013
    4 of 5 stars Reviewed 2 May 2015
    A really lovely house and fantastic location. If you are looking for peace and quiet whilst not being too far away from great places to eat, visit, cycle, shop then this is a...
    5 of 5 stars Reviewed 24 April 2014
    The villa is beautiful, the room we stayed in was spacious, comfortable, stylish, very clean and had everything we needed. The fantastic view over make a perfect surrounding for...
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    $232
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    1 / 23
    4.5 of 5 stars (4) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Ping Pong Table
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village and is within a few minutes... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena SI
    2 of 5 stars Reviewed 3 November 2014
    We cannot recommend staying at this property because it involved problems that we should not have encountered. My husband and I rented this Tuscan condo for a week at the end of...
    5 of 5 stars Reviewed 27 July 2014
    Stay for a week and had a great time. Apartment was ideal for the pool, handy for our children to nip in and out. 2 nice size bedrooms, galley kitchen and a good size...
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    $135
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    1 / 20
    5 of 5 stars (5) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Gym
    • Internet Access
    • Ping Pong Table
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    A fabulous place to relax, this apartment is at the edge of the Borgo furthest from the road. Designed in a traditional style incorporating a range of modern comforts and facilities, the apartment is the best of both worlds. Stone tiled floors with chestnut beams overhead give a smart but homely... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013
    5 of 5 stars Reviewed 30 May 2014
    We stayed there 5 nights. The apartment is located in a quiet area within a walking distance from the center of the town.The apartment is clean, comfortable and very well...
    4 of 5 stars Reviewed 27 March 2014
    Sadly only 2 nights here in this beautiful quiet village. Accommodation was great, large rooms, well equipped and clean. Nothing to complain about at all. Would love to return.
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    $171
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    1 / 36
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Typical Chianti estate with a fully renovated barn to rent, and two other accommodations, with pool, olive trees, typical Chianti scenery between Gaiole in Chianti and Radda in Chianti. The Chianti Classico area is rich in wineries and wine producing properties, and wordly known for its wine... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    5 of 5 stars Reviewed 27 January 2015
    A great place to travel throughout Tuscany. Hospitable hosts made our trip memorable - their advice about nearest restorants and POI was extremely helpful. We were at La Casa in...
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    $70
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    1 / 12
    1 Bedroom / 1 Bathroom / Sleeps 3
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    • Grill
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    'Trebbiano n°5', 2-room apartment 40 m2, on the lower ground floor: living/dining room with satellite TV. 1 double bedroom with 1 bed and 1 double bed. Kitchenette. Shower/WC. Maximum 1 pet/ dog allowed. Included: Power costs, Gas, Laundry (initial supply of bed linen and towels), No Local Tax... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013
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    $2,696
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    1 / 17
    4 of 5 stars (1) Very good
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa. The restoration works have been done preserving carefully all the ancient characteristics such as the outside stones, the vaulted or wooden beamed... View all property information
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    Gaiole in Chianti, Province of Siena X
    4 of 5 stars Reviewed 20 August 2013
    We spent 2 weeks at this wonderful historic home with friends. The house was spacious for 8 people with separate areas to relax if desired. The building has been restored with...
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    $884
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    1 / 21
    4 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    One of Italy's national monuments; Montefienali hamlet emerged in the middle of the 13th Century as a remote staging post on an ancient Roman road into the Chianti. After a two-year restoration project Montefienali is once more the ideal place for rest and recuperation for both body and mind and an... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena ITALY
    4 of 5 stars Reviewed 17 January 2014
    We enjoyed our time at the villa. It was very quiet as it was off season so we relaxed outside the villa and went on trips to Florence and Sienna. A car is essential to get to...
    4 of 5 stars Reviewed 14 January 2012
    My partner and I booked this one for a family wedding in Radda in Chianti. Other family menbers and guests booked other villas on the complex. This particular villa is secluded...
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    5 of 5 stars (11) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ping Pong Table
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships. The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with solid stone walls, chestnut beams and... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 53013 SI
    5 of 5 stars Reviewed 13 July 2014
    My husband and I stayed for four nights in this wonderful and clean apartment in the heart of Chianti. Phil was extremely responsive and helpful throughout the booking process and...
    5 of 5 stars Reviewed 22 June 2014
    Casacorvo Minore -- what a perfect place to call home for six days! Phil was terrific to deal with right from our first enquiry. (And we had the added pleasure of meeting him at...
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    $2,417
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    1 / 23
    5 of 5 stars (2) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    The property is in a great location only five minutes away from Gaiole with all the amenities a large town has to offer. The property is surrounded by a lovely mature garden with an attractive private pool which is set in a secluded area of the garden partly screened by mature hedging and trees... View all property information
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    Gaiole in Chianti, Province of Siena ITALY
    5 of 5 stars Reviewed 5 June 2012
    Fantastic holiday. Villa was perfect with plenty of social areas. Villa contained everything you could have hoped for, i.e. in the utility room and kitchens. Walking distance to...
    5 of 5 stars Reviewed 5 November 2011
    Sue who owns the property and lives next door was a perfect host and very laid back, just like us, we were there for a 40th Birthday celebration and couldnt have wished for a...
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    $135
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    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dryer
    • Gym
    • Internet Access
    • Mountain Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The traditional Tuscan style cool stone walls, terracotta floors and dark chestnut beams give a pleasant, relaxed atmosphere to the interior of the apartment which also has air conditioning/central heating and double glazing. The kitchen is well-equipped with full-sized oven and hob, microwave,... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $2,354
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    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
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    • Balcony
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Inside the villa there is a spacious lounge with a double sofa and sat TV. Passing under a terracotta arch there is the kitchen and dining area. The kitchen is with gas hobs, oven, and a small fridge. From the lounge through another terracotta arch is a corridor off which there is access to the... View all property information
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    Gaiole in Chianti, Province of Siena ITALY
    5 of 5 stars Reviewed 30 August 2014
    I was looking for a way to show Tuscany to my children that was a little different from staying in a hotel in Florence and renting a property in the Chianti region was the right...
    5 of 5 stars Reviewed 31 May 2013
    The apartment itself is great but it's the outside area which makes it such a lovely place to stay. Overlooking the Tuscan countryside and vineyards, you'll want to spend all your...
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    $2,124
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    In the heart of the Chianti Classico is where you'll find this house and it's location is not only to be appreciated because it's a short drive to town, but because it's set high on a hill with magnificent views of the surrounding vineyards and olive groves. At this Italian accommodation you'll be... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $129
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    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms / 4 Bathrooms / Sleeps 6
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    5 of 5 stars Reviewed 4 December 2014
    Un ottimo contatto con i proprietari Donatella e Santo che stanno prendendo quattro per noi; Una posizione molto buona che permette per la spesa quotidiana al villaggio e quindi...
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    $999
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    5 of 5 stars (1) Excellent
    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    5 of 5 stars Reviewed 19 June 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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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Garden
    • Grill
    • Internet Access
    • Mountain Views
    • Pool
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Fresh air, picturesque panoramas, tranquility and privacy await you at this dream location in the hills of Chianti. BEL SORRISO, the house of the Beautiful Smile, is part of a meticulously restored 14th-century village in CHIANTI that is today designated as a national monument. Occupying the main... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $666
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    1 / 22
    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximity to numerous wineries,... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    4 of 5 stars Reviewed 18 June 2014
    We stayed Fontecaresino 1 over the Easter holiday period and were very impressed. A real gem hidden in the hills. The surrounding gardens where beautiful and well kept. While it...
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    $1,414
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    5 of 5 stars (12) Excellent
    5 Bedrooms / 5 Bathrooms / Sleeps 13
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Gym
    • Housekeeping...
    • Ping Pong Table
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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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    Gaiole in Chianti, Province of Siena 53013
    5 of 5 stars Reviewed 9 October 2014
    Villa Le Pratola offers a truly Italian experience in the Chianti countryside of Tuscany. Relax in the infinity pool and enjoy spectacular views of the countryside vineyards and...
    5 of 5 stars Reviewed 3 October 2014
    Our stay at Le Pratola was a highlight of our Italian trip this fall. The property is so beautifully maintained with amazing views. The rooms are large and comfortably...
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    $1,013
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    4.5 of 5 stars (3) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Beautiful Family Villa in Borgo di Gaiole, surrounded by the Chianti hills covered in vineyards and olive groves, just a 100 meters walk from the quiet village of Gaiole in Chianti, a typical Tuscan hamlet with restaurants, shops and amenities, an ideally located between Siena and Florence. It is... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    5 of 5 stars Reviewed 10 July 2013
    We had a wonderful 10 day stay in Villa Gaiole. The villa is located in a small residential area, a short stroll from the main hub of the quaint village of Gaiole. The town itself...
    4 of 5 stars Reviewed 21 July 2014
    We hadden een fijne vakantie met 6 volwassenen in Villa Gaiole. Het is een erg gezellig dorpje met een goede uitvalsbasis voor bezoeken aan bv Siena, San Gimignano,... Een héél...
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    $482
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    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Ping Pong Table
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    The well equipped property has four double bedrooms and three bathrooms on two levels with the lower level lounge easily converting into a fifth double bedroom. A spacious lower level hallway makes for good storage space for large party holiday baggage, with additional storage arrangements... View all property information
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    Gaiole in Chianti, Province of Siena 53013 SI
    5 of 5 stars Reviewed 26 October 2011
    My Husband and I stayed here with a group of our friends for a week. It was the perfect size and location. Great for day trips to the hill towns of Tuscany or just hanging out...
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    $112
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    1 Bedroom / 1 Bathroom / Sleeps 3
    traveller have booked this property
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.Terreno Porzione privata del terreno, giardino, lastre. Parcheggio: 1 x posto macchina in garage sotterraneo. Accesso alla casa tramite... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    From
    $4,850
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    1 / 12
    5 Bedrooms / 5 Bathrooms / Sleeps 18
    Overview Make Enquiry
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    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is a traditional 5 bedroom villa situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total as additional apartments are available within the grounds, it's an ideal base for a stay with family or friends. The wonderful gardens and exceptionally... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    From
    $186
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    1 / 24
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Hot Tub
    • Ping Pong Table
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    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... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $101
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    1 / 28
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Appartamento Gaiole 13 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view of the surrounding hills.... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    From
    $459
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    1 / 17
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This beautiful, detached farmhouse has been carefully restored by the architect owner to the highest standards. He has maintained the original structure, while adding modern design ideas. This has produced a light and airy property with comfortable internal furnishings and beautiful outdoor spaces.... View all property information
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    Location Information
    Gaiole in Chianti, Province of Siena 06019
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    1 / 17
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Le Diacce villa, benefits of a total privacy and enjoys splendid sunsets and a beautiful pool. The living room and kitchen open onto spacious terraces fully equipped for outdoor dining and surrounded by lawns, gardens and ancient trees. Ideal for families or a group of friends with plenty to see... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    From
    $1,711
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    1 / 24
    7 Bedrooms / 7 Bathrooms / Sleeps 13
    Overview Make Enquiry
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    • Internet Access
    • Private Outdoor...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • 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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    Gaiole in Chianti, Province of Siena 53013
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    $4,807
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    1 / 12
    7 Bedrooms / 8 Bathrooms / Sleeps 18
    Overview Make Enquiry
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    • Balcony
    • Fireplace
    • Grill
    • Hot Tub
    • Ocean Views
    • Private Outdoor...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • 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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    Gaiole in Chianti, Province of Siena 53013
    From
    $4,136
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    1 / 16
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    [L A Y O U T] Ground Floor: Large sitting room and kitchen both opening onto the front terrace; Master bedroom with four poster bed, en-suite bathroom (Jacuzzi bath and separate shower) and walk-in wardrobe; Master bedroom with four poster bed and en-suite bathroom (jacuzzi bath, separate shower);... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $1,425
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    1 / 24
    3 Bedrooms / 1 Bathroom / Sleeps 5
    traveller have booked this property
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    Amenities & Details
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Mountain Views
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    ' IL BACCHINO IN CHIANTI ' è una antica casa colonica rustica nel cuore della Toscana. Questo caratteristico casale in pietra del 1500, accuratamente ristrutturato, affonda le sue radici intorno all'XI secolo d.c.: le fondamenta murarie e le cantine della struttura risalgono a tale periodo... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    From
    $563
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    1 / 22
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Gym
    • Internet Access
    • Ping Pong Table
    • Satellite TV
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This beautiful and tastefully furnished 1 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful Siena The apartment is... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $4,279
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    1 / 24
    6 Bedrooms / 7 Bathrooms / Sleeps 16
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • 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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    Gaiole in Chianti, Province of Siena 53013
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    $68
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    1 / 18
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    'Cerbiatto n°5A', 2-room apartment 35 m2 on 2 levels, on the ground floor: living/dining room with satellite TV. Kitchenette (4 hot plates). On the lower ground floor: 1 double bedroom. Shower/bidet/WC. Small patio. Terrace furniture. Please note: The showwer has not shower-try. Included: Power... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $94
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    1 / 33
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    'La Colomba n°4', 3-room apartment 75 m2 on 2 levels, on the ground floor: living room with 1 double sofabed (160 cm), satellite TV. Kitchenette (4 hot plates). Shower/WC. Upper floor: 1 double bedroom. 1 room, 2 beds. Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 pet/ dog allowed.... View all property information
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    Gaiole in Chianti, Province of Siena 53013
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    $94
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    1 / 22
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    'La Farfalla n°5', 3-room apartment 75 m2 on 2 levels, on the ground floor: living/dining room with 1 double sofabed (160 cm), satellite TV. Kitchenette (4 hot plates). Sep. WC. Upper floor: 1 double bedroom. 1 room, 2 beds. Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 pet/ dog... View all property information
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    Gaiole in Chianti, Province of Siena 53013
    From
    $110
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Fireplace
    • Grill
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    'San Giovese n°4', 4-room apartment 105 m2, on the upper ground floor: living room with satellite TV. 1 room with 1 bed and 1 double bed. 1 double bedroom. 1 room with 1 bed. Kitchen (4 hot plates, dishwasher) with open-hearth fireplace and dining table. Shower/WC, shower/bidet/WC. Maximum 1 pet/... View all property information
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    Gaiole in Chianti, Province of Siena 53013