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Vacation Rentals in Gaiole in Chianti, Italy

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    Travelers to Gaiole in Chianti are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 27
    4 of 5 stars (11) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 20
    5 of 5 stars (6) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Welcome at your home. A home of dolce far niente and serene silence, of truffles and olives, of light and land, by sunny lounge and fine dining in the shade of green and old stones. But also a home to markets and culture, from high altitude villages and magnificent cities, of architecture,... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 42
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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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    53013, Gaiole in Chianti, Province of Siena
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Porch
    • Central Heating
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    53013, Gaiole in Chianti, Province of Siena
    1 / 12
    5 of 5 stars (14) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Balcony
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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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    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed April 4, 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 June 21, 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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    1 / 64
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    PRIVATE STRUCTURE. Lo Spicchio is a beautiful farmhouse situated in the heart of Chianti on a hill with one of the most beautiful natural scenarios in the Siena area and in which the leading role is played by infinite shades of green. From the large windows in the living room and from the lush... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 27
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
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    • Pet-friendly
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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... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    4 of 5 stars Reviewed October 30, 2015
    a lovely cottage set in the beautiful Chianti region. our host and his family were very welcoming and helpful, from leaving us a bottle of wine from the family vineyard, to...
    5 of 5 stars Reviewed August 5, 2015
    I loved this property. It is an attractive blend of rusticity and convenience. The kitchen is complete and well stocked, making cooking easy, a major consideration for me as I...
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    In the top of a hill set in the patchwork of vineyards that characterizes the area of Chianti Classico, in the heart of an ancient medieval village, was born a few years ago La Pieve Marsina. The structure, made up of 5 nice apartments, has as principal objective to allow our guests to enjoy the... View all property information
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    53013, Gaiole in Chianti, Province of Siena
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Yard
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    About this property
    In the top of a hill set in the patchwork of vineyards that characterizes the area of Chianti Classico, in the heart of an ancient medieval village, was born a few years ago La Pieve Marsina. The structure, made up of 5 nice apartments, has as principal objective to allow our guests to enjoy the... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    53013, Gaiole in Chianti, Province of Siena
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    53013, Gaiole in Chianti, Province of Siena
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Mountain Views
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    • Central Heating
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    53013, Gaiole in Chianti, Province of Siena
    1 / 40
    4.5 of 5 stars (6) Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    • Ocean Views
    • Sauna
    • Mountain Views
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    About this property
    NEW MANAGEMENT from Summer 2015 Villa Albizi Tuscany life and more….for groups of friends or large families Villa Albizi is normally rented on a villa-only weekly basis and are ideal for those seeking independence and privacy. We have created a formula designed to offer privacy, flexibility and... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed October 1, 2015
    We have only visited Villa Albizi for one day, did not stay over night in September 2015 because of our tight schedule. We met the owners Ilaria and Thomasso and their friend...
    4 of 5 stars Reviewed September 4, 2015
    We were part of large family group who came here for a 25th Wedding Anniversary, I did not actually stay in the villa but had an apartment within the small lovely hamlet. I did...
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Balcony
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    About this property
    2 Villas (1 FONTECARESINO and 2 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 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 12
    5 of 5 stars (1) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    • Internet Access
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    • x
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    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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    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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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • x
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    • 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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    53013, Gaiole in Chianti, Province of Siena
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • 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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    53013, Gaiole in Chianti, Province of Siena
    1 / 28
    5 of 5 stars (11) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Pet-friendly
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    About this property
    VILLA LISIDOR IS NOW GETTING FULLY RENOVATED AND WILL BE READY END OF FEBRUARY 2016; BOOKINGS ACCEPTED FOR WEEKS STARTING FROM APRIL 2016. BOOKINGS MADE WITHIN END OF JANUARY ARE PROMOTED WITH 15% DISCOUNT ON RATES 2016. BE THE FIRST ONE TO ENTER OUR NEW LUXURY VILLA!! The habitable area will be... View all property information
    Location Information
    53010, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed July 3, 2015
    We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an...
    5 of 5 stars Reviewed May 5, 2014
    Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be...
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Washer
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    • x
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    53013, Gaiole in Chianti, Province of Siena
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Appartamento Gaiole 40 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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    53013, Gaiole in Chianti, Province of Siena
    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Private Outdoor...
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    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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    53013, Gaiole in Chianti, Province of Siena
    4 of 5 stars Reviewed June 29, 2013
    This was our second time here. Last year, the weather was great, so we virtually lived outside, which is the best part of this property. This year, it was quite cool, even cold in...
    3 of 5 stars Reviewed November 3, 2012
    It was a good experience. We used the villa as our base for day trips, and it was centrally located. Nestled among the vineyards, it was quintessential Tuscany. The central...
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    5 Bedrooms, 4 Bathrooms, Sleeps 23 | Quick View
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    • Central Heating
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    53013, Gaiole in Chianti, Province of Siena
    1 / 27
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Casa Refolo F is a welcoming apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps two people. From Casa Refolo F you will have a pleasant view of the garden and of the vineyards. Casa Refolo F is 70 square meters (750 square feet). It features a shared swimming... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Yard
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    About this property
    Casa Refolo C is a characteristic apartment that is part of a villa. It sleeps six people. It is appoximately 150 square meters (1615 square feet). It features a shared swimming pool, a private patio, a shared garden and winter heating. You will be roughly 3 km (1.8 miles) from Gaiole in Chianti,... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 22
    5 of 5 stars (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed August 23, 2015
    Right in the heart of Chiantishire, my five mature children and I enjoyed a splendid week, viewing the sights of Tuscany in the morning and sunning by the huge, huge, sparkling...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    'Il Ghiro n°8', 3-room apartment 65 m2, on the ground floor: living room with 1 double sofabed (160 cm), satellite TV. 1 double bedroom. 1 room with 2 beds. Kitchenette (4 hot plates). Shower/WC. Small patio. Terrace furniture. Included: No Local Tax charged for children, Electricity, Water,... View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Podere Scopeto is a former Chianti hill farm on the west-facing slopes of the Montagni di Chianti. The present owners bought it some 15 years ago and restored the farmhouse and a separate self-contained studio for family holidays. It has kept its family feel and charm. The main house sleeps 10... View all property information
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    53013, Gaiole in Chianti, Province of Siena
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    5 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Perfect for a quiet getaway, family reunion or tour of the Chianti Classico region, Il Colombaio is a secluded seven-bedroom farmhouse. Recently restored by an American family, the property features original Tuscan charm and stunning panoramic views as well as modern touches like a pool and... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 19
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 76
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 26
    12 Bedrooms, 11 Bathrooms, Sleeps 24 | Quick View
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    • DVD Player
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    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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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    52022, Gaiole in Chianti, Province of Siena
    1 / 16
    6 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    • Central Heating
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    About this property
    Perfect for a quiet getaway, family reunion or tour of the Chianti Classico region, Il Colombaio is a secluded seven-bedroom farmhouse. Recently restored by an American family, the property features original Tuscan charm and stunning panoramic views as well as modern touches like a pool and... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 23
    3 of 5 stars (1) Average
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday apartments, where visitors can... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    3 of 5 stars Reviewed November 9, 2015
    One of the reasons we chose the place was because although remote, it had a restaurant so, with a small child, this would make things more convenient. When arrived unfortunately...
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    5 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    • x
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    About this property
    This is a traditional 5 bedroom villa and adjacent 1 bedroom apartment situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total due to the additional apartment that is available within the grounds, it's an ideal base for a stay with family or... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 102
    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    About this property
    This exclusive villa with private swimming pool and tennis court offers luxurious accommodation in Tuscany for 13 people. The apartments and farmhouse can be rented separately or combined with the villa to accommodate up to 35 guests. This exclusive villa with private swimming pool and tennis court... View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Mountain Views
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • ?
    • x
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    • 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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    53013, Gaiole in Chianti, Province of Siena
    1 / 24
    5 of 5 stars (32) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed September 29, 2015
    We stayed at Tracey and John's Gaiole apartment for five nights in September 2015. As soon as we arrived we knew we were somewhere special. The view is sensational! We enjoyed...
    5 of 5 stars Reviewed June 30, 2015
    We spent a week staying at this apartment in Gaiole and would highly recommend it. The booking process was very easy and the English owners, John and Tracy, were most responsive...
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    1 / 17
    4 of 5 stars (1) Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    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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    53013, Gaiole in Chianti, Province of Siena
    4 of 5 stars Reviewed August 19, 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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Mountain Views
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    • Pet-friendly
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    • x
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    About this property
    In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its green vineyards, you will find the Podere Lucignano Secondo Agriturismo, a mansion built in 1898, now elegantly restored and turned into an exclusive relais. The Podere... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 23
    5 of 5 stars (12) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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
    Location Information
    53013 SI, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed May 28, 2015
    Casacorvo Maggiore is a superb apartment; very well equipped and comfortably furnished. There's a great selection of games, DVDs and novels, and plenty of maps, guidebooks and...
    5 of 5 stars Reviewed November 9, 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...
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    1 / 21
    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    • Pet-friendly
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    About this property
    This is a fabulous 7 bedroom luxury villa in Tuscany, sleeping up to 13 guests. Immaculately presented and beautifully furnished, the villa provides guests with a luxurious base from which to enjoy their holiday in Tuscany. Outside guests enjoy exclusive use of a private swimming pool and tennis... View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • Pet-friendly
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    • Elder access
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    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... View all property information
    Location Information
    53100, Gaiole in Chianti, Province of Siena
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Sauna
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    About this property
    Extensively renovated to showcase the comforts of the 21st Century with the charm of the 16th Century – A true Tuscan experience with authentic wood-burning pizza oven, farm fresh eggs, organic garden, and extra virgin olive oil from the estate olive grove. A stay in luminous Tuscany deserves... View all property information
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    53013, Gaiole in Chianti, Province of Siena
    1 / 44
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • x
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    About this property
    Typical Chianti estate with a fully renovated barn (6) to rent, and two other units in the main house for a total of 10, with pool, olive trees, typical Chianti scenery between Gaiole in Chianti and Radda in Chianti. The house can accommodate from 4 people, to 10 people in the same unit (5... View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    4 of 5 stars Reviewed October 13, 2015
    Fabulous place and a lovely warm welcome from Nicoletta. The temperature dropped at night and was a bit chilly for us North Queensland people, so Nicoletta's lovely father...
    5 of 5 stars Reviewed October 8, 2015
    My wife, two teenage children, a friend, and I recently stayed at La Casa in Chianti in Gaiole, Tuscany. We were absolutely delighted with the beautiful stone-built home, the...
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    1 / 18
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 2 | Quick View
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    • Terrace
    • Shared Yard
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    • Pet-friendly
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    Location Information
    53013, Gaiole in Chianti, Province of Siena