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Holiday villas in Gaiole in Chianti, Italy

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All 116 Rentals in Gaiole in Chianti
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€114
Per Night
1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 2
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€90
Per Night
1 / 33
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2 Bedrooms, 1 Bathroom, Sleeps 5
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€115
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1 / 24
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3 Bedrooms, 1 Bathroom, Sleeps 6
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€50
Per Night
1 / 20
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • 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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5 of 5 stars Reviewed 29 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 26 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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From
€320
Per Night
1 / 16
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6 Bedrooms, 5 Bathrooms, Sleeps 12
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5 of 5 stars Reviewed 18 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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€1,806
Per Week
1 / 25
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4 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Dishwasher
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • 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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From
€115
Per Night
1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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5 of 5 stars Reviewed 23 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...
5 of 5 stars Reviewed 21 April 2014
I've spent, with my family, few days last October in this charmy country house located in the heart of chiantishire ... The house is surrounded by a wonderful landscape made by...
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From
€800
Per Week
1 / 17
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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4 of 5 stars Reviewed 17 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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From
€5,980
Per Week
1 / 40
7 Bedrooms, 7 Bathrooms, Sleeps 18
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern design with original... View all property information
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From
€454
Per Night
1 / 24
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6 Bedrooms, 5 Bathrooms, Sleeps 12
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  • Dishwasher
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Ping Pong Table
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
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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From
€88
Per Night
1 / 9
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • 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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From
€99
Per Night
1 / 21
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This beautiful and tastefully furnished 3 bedroom semi-detached villa is located in the popular hamlet of Gaiole in Chianti, near Siena in Tuscany. The ground floor consists of a spacious living room with a double sofa bed, and French doors opening on the patio and front garden, with vista on the... View all property information
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From
€130
Per Night
1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • Garden
  • Hot Tub
  • Internet Access
  • Pool
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Exclusive apartment with private garden in medieval village in the heart of the Chianti Classico area, a few kilometers from Siena. Tastefully renovated, refined and lovely garden overlooking the vineyards. View all property information
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From
€70
Per Night
1 / 15
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1 Bedroom, 1 Bathroom, Sleeps 3
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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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From
€213
Per Night
1 / 22
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a Tuscan rustic style and... View all property information
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From
€170
Per Night
1 / 20
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1 Bedroom, 2 Bathrooms, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Luxury 1Bedroom unit in the heart of Chianti,surrounded by Vineyards. Master bedroom with kingsize bed, writing desk and chair and exceptional bath. The lounge is comfortably furnished with two leather sofas and chairs, and has a flat screen TV with DVD and video player at one end. Private... View all property information
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From
€115
Per Night
1 / 54
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Garden
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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From
€115
Per Night
1 / 24
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3 Bedrooms, 1 Bathroom, Sleeps 5
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  • 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
' 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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From
€100
Per Night
1 / 11
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2 Bedrooms, 1 Bathroom, Sleeps 5
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  • Air Conditioning
  • Mountain Views
  • 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
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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From
€395
Per Week
1 / 20
1 Bedroom, 1 Bathroom, Sleeps 3
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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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5 of 5 stars Reviewed 21 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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From
€70
Per Night
1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 2
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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From
€3,000
Per Week
1 / 24
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6 Bedrooms, 7 Bathrooms, Sleeps 14
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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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From
€500
Per Week
1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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From
€90
Per Night
1 / 10
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2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Balcony
  • Fireplace
  • Hot Tub
  • Ping Pong Table
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
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 Pieve Marsina. The structure, made up of nice apartments, has as principal objective to allow our guests to enjoy the calm,... View all property information
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From
€512
Per Night
1 / 26
12 Bedrooms, 11 Bathrooms, Sleeps 24
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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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From
€70
Per Night
1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 3
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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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From
€200
Per Night
1 / 20
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2 Bedrooms, 3 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Located at the second floor,amazing 2bedrooms unit in the heart of Chianti, surrounded by Vineyards. A master bedroom with a kingsize bed, writing desk and chairs and a view over the hamlet and gardens, located next door there is a bathroom with full size bath and hand held shower. The other... View all property information
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From
€450
Per Night
1 / 16
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5 Bedrooms, 4 Bathrooms, Sleeps 23
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From
€800
Per Week
1 / 18
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4 Bedrooms, 5 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • 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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From
€1,200
Per Night
1 / 102
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7 Bedrooms, 7 Bathrooms, Sleeps 13
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Amenities & Details
  • Dishwasher
  • Garden
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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. Additional amenities include: heating. View all property information
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From
€80
Per Night
1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • 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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From
€55
Per Night
1 / 15
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3 Bedrooms, 2 Bathrooms, Sleeps 5
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From
€99
Per Night
1 / 9
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1 Bedroom, 1 Bathroom, Sleeps 4
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From
€541
Per Week
1 / 19
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1 Bedroom, 1 Bathroom, Sleeps 4
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1 / 11
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2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
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Amenities & Details
  • Balcony
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Located in an excellent position to visit the typical villages of Chianti, just a few minutes from Gaiole in Chainti country cycling event the heroic and Siena famous for the Palio of Siena, is ideal to stop the daily routine for a stroll walk immersed in an enchanting nature, visit the nearby... View all property information
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5 of 5 stars Reviewed 20 August 2013
Il Poggetto is a steal at the price you pay. Situated in the middle of Tuscany, on a small hilltop within a very small village, you are away from the main tourist areas and the...
4 of 5 stars Reviewed 30 September 2014
Carino economico logisticamente ottimo per visitare il chianti e siena ottimo per il giro delle tre citta firenze siena arezzo.
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From
€220
Per Night
1 / 15
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6 Bedrooms, 9 Bathrooms, Sleeps 12
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From
€69
Per Night
1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
€99
Per Night
1 / 8
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2 Bedrooms, 1 Bathroom, Sleeps 4
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From
€300
Per Night
1 / 18
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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From
€1,695
Per Week
1 / 23
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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5 of 5 stars Reviewed 4 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 4 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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From
€125
Per Night
1 / 11
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3 Bedrooms, 4 Bathrooms, Sleeps 9
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From
€1,850
Per Week
1 / 18
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6 Bedrooms, 8 Bathrooms, Sleeps 14
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From
€114
Per Night
1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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From
€5,500
Per Week
1 / 24
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5 Bedrooms, 15 Bathrooms, Sleeps 10
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From
€595
Per Week
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • 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
The apartment is just 5 minutes walk from the center of Gaiole, where you will find all the services you need. Like restaurants, bars, wineshops, banks, food shop, hairdressers etc. Gaiole is one of several traditional Chianti villages in the region. Others worth visiting include Radda, Greve and... View all property information
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5 of 5 stars Reviewed 3 October 2013
After considerable searching around Tuscany for a suitable apartment for a one week stay we happened across Borgo Tower. The discovery I will attribute to our friends who...
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From
€120
Per Night
1 / 5
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2 Bedrooms, 4 Bathrooms, Sleeps 6
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From
€70
Per Night
1 / 18
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 2
Booking
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From
€1,140
Per Week
1 / 23
2 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Dishwasher
  • Grill
  • Private Pool
  • 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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From
€2,850
Per Week
1 / 60
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Garden
  • Internet Access
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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5 of 5 stars Reviewed 22 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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5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • 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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Suitability

  • Wheelchair access (2)
  • Elder access (31)
  • Suitable for children (67)
  • Pet friendly (28)
  • Smoking allowed (25)

Amenities

  • All pools (85)
  • Parking (80)
  • Internet (66)
  • Public pool (58)
  • Garden (56)
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