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Vacation Rentals in Gaiole in Chianti, Italy

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    Travellers to Gaiole in Chianti are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Gaiole in Chianti, Province of Siena
    1 / 26
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    On the highest point of a hill set among the mosaic of the vineyards, typical of the Chianti Classico area, in the heart of a medieval village, you'll find the Pieve Marsina. The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 24
    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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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
    1 / 17
    5 of 5 stars (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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.<BR><BR>Ideal for families or a group of friends with plenty to... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Casa Refolo B is a welcoming apartment that is part of a villa in the characteristic style of the Tuscan countryside. It sleeps six people. It is appoximately 160 square meters (1720 square feet). It features a shared swimming pool, a private patio, a shared garden and winter heating. You will be... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Agriturismo Podere Terrena is the best place to give your-self a time-less and extraordinary experience. A beautiful and peaceful location to remember for the whole life. The building is an old "borghetto" of thick stone's walls and "terracotta" tile roof situated in a little valley where river... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartment Gaiole Suites 4 is... View all property information
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    Gaiole in Chianti, Province of Siena
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    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartment Gaiole Suites 3 is... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Gaiole in Chianti, Province of Siena
    1 / 16
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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
    1 / 48
    Private Room, 2 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
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    About this property
    This beautifull restructured 16th century house sits on a hillside and dominates the sorrounding countryside as far as the eye can see. Nestled in the heart of Chianti our B&B is perfectly located for the week-end break, walking or cycling holidays as well as trekking among the castels. Come visit... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 26
    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    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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    Gaiole in Chianti, Province of Siena
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    11 Bedrooms, 11 Bathrooms, Sleeps 22 | Quick View
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    • x
    About this property
    Beautiful Renaissance farmhouse built round a rustic characteristic threshing-floor in a fine panoramic position over Meleto Castle and the medieval village of Vertine. It has been recently fully restored and transformed into a prestigious villa with 4 apartments with every comfort. The furnishing... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Garden
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    • Pet-friendly
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    • ?
    • ?
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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 4.5 km (2.8 miles) from Gaiole in Chianti,... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Garden
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Gaiole Suites is a compound of terraced houses, just renewed, situated 500m away from Gaiole in Chianti center, in a quiet zone, silent and not familiar with rush hour since the traffic is very little. It is surrounded by the green Tuscany hills. The beautiful apartment Gaiole Suites 7, which can... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Porch
    • Patio
    • Parking
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
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    Gaiole in Chianti, Province of Siena
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
    • Balcony
    • Satellite TV
    • Grill
    • Internet Access
    • Children's Pool
    • Parking
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close... View all property information
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    Gaiole in Chianti, Province of Siena
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    1 / 30
    5 of 5 stars (1) Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • Private Garden
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    • Patio
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This is a unique and historic wine country villa set in the heart of one of the most famous wine countries in the world, Chianti. The Tower was built in 1085, making it nearly 1000 years young. The interior has been completely remodeled and outfitted with all of the modern amenities. Contemporary... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Air Conditioning
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned. Availability of apartments an... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 20
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Central Heating
    • Satellite TV
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    • Shared Garden
    • Terrace
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
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    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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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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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    Gaiole in Chianti, Province of Siena
    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Borgo di Gaiole, is an ancient town in the heart of Chianti hills. This area is famous all over the world for the typical products and therefore known destination for wine tourism. Here, also, there are all finds of shops and restaurants. Siena, the wonderful city that hosts the Palio, is about a... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • Balcony
    • Mountain Views
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 32
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • ?
    About this property
    Casa Refolo A is a characteristic two-story apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps six people. It is appoximately 130 square meters (1400 square feet). It features a shared swimming pool, a private patio, a shared garden and winter heating. You will be... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 14
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
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    • Pet-friendly
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    Gaiole in Chianti, Province of Siena
    1 / 14
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Gaiole in Chianti, Province of Siena
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Gaiole in Chianti, Province of Siena
    1 / 16
    5 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • Central Heating
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    Gaiole in Chianti, Province of Siena
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    About this property
    Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence.<BR><BR>Moreover, you can go trekking in the beautiful trails and nature walks on foot or... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 54
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Internet Access
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    • Washer
    • Mountain Views
    • Satellite TV
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    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    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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    Gaiole in Chianti, Province of Siena
    1 / 45
    6 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Nestled in the lush nature of the Chianti region, this charming manor built in the early 1900s lovingly embraces and preserves the romance of bygone times. It is an ideal place for relaxing in the surrounding nature while enjoying the area’s superb foods and wines. The house comprises about 800... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 25
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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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    Gaiole in Chianti, Province of Siena
    1 / 17
    4 of 5 stars (1) Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    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
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    About this property
    The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside.<BR>Outside a portion of an equipped courtyard is available for the exclusive use of the... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 40
    7 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    • x
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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
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    Gaiole in Chianti, Province of Siena
    1 / 30
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • x
    About this property
    The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your memories. In the heart of the Chianti, surrounded by woodlands and vineyards, this ancient construction has opened its doors to tourists who wish to have a rare and unique... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    About this property
    The Gaiole area, with its woods, vinyards and olivegroves, can be discovered on foot, on horseback, by bike or any other means of transport you prefer.The tourist information office in Gaiole will supply you with detailed route descriptions and maps, wich will guide you along well signposted paths... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 48
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Porch
    • Central Heating
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    Gaiole in Chianti, Province of Siena
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    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Washer
    • Shared Outdoor Pool...
    • Balcony
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    IL BORGHETTO Costruito con pietre millenari, questo bellissimo Borghetto, 'Terrena', ha una data che risale al 1669 ed è stato completamente ricostruito e in parte ristrutturato. Oggi è un’Azienda Agricola con attività anche agrituristica perché adatta a chi desidera praticare turismo in Toscana... View all property information
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    Gaiole in Chianti, Province of Siena
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Internet Access
    • Central Heating
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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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    Gaiole in Chianti, Province of Siena
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Private Garden
    • Shared Outdoor Pool...
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Casa Eolo is immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The village has been completely restructured for... View all property information
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    Gaiole in Chianti, Province of Siena
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    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
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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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    Gaiole in Chianti, Province of Siena
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Shared Outdoor Pool...
    • Central Heating
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your memories. In the heart of the Chianti, surrounded by woodlands and vineyards, this ancient construction has opened its doors to tourists who wish to have a rare and unique... View all property information
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    Gaiole in Chianti, Province of Siena
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    La Pieve Marsina Country retreat, in the heart of the senese Chianti offers a unique mix through tradition, relax and taste. The atmosphere of an old Medieval Hamlet and its last renovation, which aimed to preserve the architectural tradition of this area, wisely merge with the comfort and a... View all property information
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    Gaiole in Chianti, Province of Siena
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Shared Outdoor Pool...
    • Parking
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your memories. In the heart of the Chianti, surrounded by woodlands and vineyards, this ancient construction has opened its doors to tourists who wish to have a rare and unique... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 4
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    La stanza della Luna è composta da un ampio soggiorno con divano letto più una camera matrimoniale con bagno. La struttura è posta all'interno di un agriturismo ad uso Bed & Breakfast. Immersa nel verde delle colline del Chianti può offrirvi un accogliente punto di riferimento per i vostri viaggi... View all property information
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    Gaiole in Chianti, Province of Siena
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Internet Access
    • Shared Outdoor Pool...
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Gaiole in Chianti, Province of Siena