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Luxury 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.
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Get a taste of Italy’s aristocratic past and stylish present at Villa Vistarenni in Chianti. The stately seven-bedroom villa dates from the 17th century and has a 16th-century chapel perfect for special events. Larger parties can book additional accommodations on the same estate, which have room... View all property information
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    53013, Gaiole in Chianti, Province of Siena
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Grill
    • Shared Outdoor Pool...
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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
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    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    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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    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
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Central Heating
    • Private Outdoor...
    • Patio
    • Internet Access
    • Satellite TV
    • Grill
    • Mountain Views
    • Balcony
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    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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    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    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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    5 of 5 stars (17) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    • Child-friendly
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    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 a heated pool and at 6458 sq ft Le Pratola has 5 air conditioned... View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    5 of 5 stars Reviewed October 12, 2015
    Great location close to Rhadda, Gaiole, Sienna. Perfect size for 5 couples. Large bedrooms with ensuites. Big modern kitchen & dining room, dish washer, washer & dryer, wi-fi...
    5 of 5 stars Reviewed September 22, 2015
    The villa was absolutely spectacular! It looked wonderful from the website, but it was even more wonderful in person. The villa is extremely well maintained & Margherita was...
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
    • Hot Tub
    • Mountain Views
    • Sauna
    • Air Conditioning
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    • Satellite TV
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    • Pet-friendly
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    • Child-friendly
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
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    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
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    7 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    • Central Heating
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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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    Gaiole in Chianti, Province of Siena
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    11 Bedrooms, 11 Bathrooms, Sleeps 22 | Quick View
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    • Smoking allowed
    • Elder access
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    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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    53013, Gaiole in Chianti, Province of Siena
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    5 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
    • DVD Player
    • Central Heating
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
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    5 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    • Parking
    • Central Heating
    • Outdoor Dining Area
    • Washer
    • Private Outdoor...
    • Balcony
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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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
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    5 of 5 stars (1) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
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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
    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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    9 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
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    12 Bedrooms, 11 Bathrooms, Sleeps 24 | Quick View
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    • DVD Player
    • Patio
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    • Grill
    • Washer
    • Air Conditioning
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
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    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
    Location Information
    52022, Gaiole in Chianti, Province of Siena
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    1 / 76
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Grill
    • Private Outdoor...
    • Air Conditioning
    • Washer
    • Wi-Fi
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    • 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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
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    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Washer
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Balcony
    • Grill
    • DVD Player
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • 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
    Location Information
    53013, Gaiole in Chianti, Province of Siena