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Gaiole in Chianti Holiday Vacation with Pools

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    Travellers to Gaiole in Chianti are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    125 Matching Rentals in Gaiole in ChiantiView all 179 rentals
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    Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool1 / 20
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Our apartment in Borgo di Gaiole, Chianti1 / 21
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Chianti house, Florence, Jacuzzi, Tuscany up to 6p1 / 42
    (7)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Casacorvo Minore *2018 Early Bird Discounts*Exclusive EV Point Included*1 / 22
    (16)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2017
    We had a fantastic time in Gaiole which is in the heart of the Chianti Classico region with lots of amazing views, wineries, picturesque villages and restaurants to visit.The...
    Reviewed 14 September 2016
    relaxing by the pool, exploring beautiful are on foot or bike, enjoying good food and vine, visiting nearby historical places
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    About this property
    Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships. The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with solid stone walls, chestnut beams and...
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    53013 SI, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    San Sano hamlet in the Heart of the Chianti, the Best choice in Tuscany !1 / 21
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Balcony
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    If you are looking for a beautiful, relaxing vacation Casa del Vignaiolo is the perfect place to stay. In addition, owner Chuck is a wealth of knowledge & gave us numerous...
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    About this property
    Upon your arrival in San Sano, a quiet, medieval hamlet, surrounded by vineyards and olive groves, the drive into the small village seems very familiar as you approach. That's because it was the setting for the movie, 'Stealing Beauty' with Liv Taylor. This familiar feeling will stay with you...
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    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Perfect cottage for 2 couples with much privacy for each, secluded location1 / 26
    (14)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    As wonderful as expected - even better; in any way: Location, facilities, rooms...Perfect for trips on the countrysideVery kind ownersalso recommendable for families with...
    Reviewed 16 June 2017
    My family and i had a fantastic and absoultely relaxed holiday at PetrAlexa. You only hear the birds, when you wake up. You feel so free in the big garden and the Chianti Hills...
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    About this property
    Ciao from Petra &Alexa and thank you for stopping by! Here is what our villa offers you for a memorable stay: Villa PetrAlexa is a renovated barn, with natural stone, original beam ceilings and glass doors which offer a pleasing mix in a comfortable environment spread over two floors, granting...
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    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Casacorvo Maggiore: *2018 Early Bird Discounts*Exclusive EV Point Included*1 / 23
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2016
    It's exactly as it says on the tin. The property is very well equipped, clean and comfortable. Home from home comforts such as quality mattresses and bedding made it...
    Reviewed 28 May 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...
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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...
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    53013 SI, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Casacorvo Grande *Group Discounts*Exclusive EV Point Included*1 / 24
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casacorvo Grande is a townhouse that sits on the edge of the unique development of Borgo di Gaiole overlooking the Chianti Hills. It is a perfect location for a holiday. The accommodation comprises of two apartments, one 1bed/1bath and one 3bed/2bath, that can be combined by an internal link to...
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    53013 SI, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    castello in Chianti  conte1 / 23
    (2)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Balcony
    • Satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2017
    Wonderful old building with beautiful views over the surrounding countryside. Pool was a 5 minute walk from our apartment - nothing our kids couldn't handle, and they had a...
    Reviewed 9 November 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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    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS1 / 24
    (38)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • DVD Player
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Loved, loved this classy apartment. John and Tracy (the owners) keep it stocked with everything you could possibly need to really enjoy being at home away from home, including...
    Reviewed 6 September 2017
    We stayed at John and Tracy's for a week at the end of August/beginning of September, and had such a relaxing holiday. The apartment itself was immaculate and had everything you...
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    About this property
    Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlooks the village of Gaiole in...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    castello in Chianti ginestra1 / 25
    (1)Average
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Parking
    • Satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2016
    The location is gorgeous, high up in the mountains with fantastic views.The bedrooms were very large and there was plenty of storage space. The beds were large and...
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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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Fienile con vista sui vigneti1 / 56
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Mountain Views
    • Washer
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    The house is located in an absolute quite hill and it has a very pretty view over the chianti's vineyards. Edo and his Father were really nice and available to give us...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    LA VACANZA NEL CUORE DEL CHIANTI1 / 17
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Children's Pool
    • Grill
    • Mountain Views
    • Wi-Fi
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
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    Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.1 / 142
    (26)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Housekeeping Included
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We ran out of adjectives when trying to describe this place. Perfect location and gorgeous views. Beautifully renovated farm house inside and out with ample room for 10+ and 5...
    Reviewed 18 August 2017
    As an Australian with deep Italian ancestry, my visits to Italy are important; but none have been so intense as the absolute beauty of this amazing Tuscan villa. Le Pratola is...
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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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant property with private swimming pool, part of a historic castle located near Gaiole in Chianti, in the heart of the Chianti area. The property has a garden with lawn and a panoramic rooftop terrace with Jacuzzi and wonderful views over the surrounding countryside. It can accommodate up to 7...
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    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
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    Spacious Chianti apartment with pool access, terrace and outdoor dining area1 / 23
    (6)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
    • Terrace
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2016
    Apartment 39 in the Borgo di Gaiole complex is beautiful, spacious, clean, and well-equipped. Everything that we would hope to find was provided, as well as many small and...
    Reviewed 14 September 2015
    We stayed for a week as we had a family wedding to attend. The apartment was excellent, clean, comfortable and an amazing location. The pool was brilliant and kept our 12 year...
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    About this property
    This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village and is within a few minutes...
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    Location Information
    SI, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Exclusive and reserved in Chianti - Quercia1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Shared Garden
    • Secure Parking
    • Hot Tub
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    Loved this quiet and authentic apartment, we had everything we needed, the location was a bit remote but directions to get there clear. Beautiful outdoor area, the highlight...
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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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Sauna
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Experience the authentic Chianti life at villa LisiDor, exclusive location1 / 69
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2016
    Villa LisiDor is located in the heart of Tuscany, near Gaiole in Chianti. The property is enclosed in one of the most beautiful regions of Italy, overlooking surrounding wine...
    Reviewed 21 October 2011
    Villa Lisidor is a lovely old villa located at the top of a hill. The views are gorgeous (would be even better if the high hedge was cut down), and the property is very private...
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    About this property
    Ciao from Petra & Alexa! We warmly welcome you in our unbeatable location, discover more ... THE VILLA: Villa LisiDor has been fully renovated beginning of 2016 with all new amenities, with a habitable area of 300 square meters. On GROUND FLOOR, which is at garden level, is a large sitting room...
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    Location Information
    53010, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    TOSCANAFERIEN - PODERE L'AQUILA - OSKAR SIGRIST1 / 12
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Parking
    • Wi-Fi
    • Central Heating
    • Terrace
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Villa Podere Terrena1 / 44
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Mountain Views
    • Washer
    • Wi-Fi
    • Grill
    • Satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    A dream farmhouse , with olive trees and and beautiful countryside , surrounded by cozy villages in the Chianti region , just and over what we have imagined .. and...
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    About this property
    THE BUILDING. The building is located in a mountainous area of the classic chianti and is built entirely with local stones. It is surrounded by an olive grove from which high quality oil is obtained. The mountainous landscape with its views full of green is an invitation to relax. The whole house...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Wi-Fi
    • Mountain Views
    • Patio
    • Central Heating
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine waking up in the silence of the Tuscan countryside, in the warm morning sun, in a place full of charm and culture, surrounded by vineyards and olive trees, in the quiet hills that inspired the best artists and poets of the history. You can stop imagining, because House Losi is your...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Shared Indoor Pool
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Parking
    • Central Heating
    • Outdoor Dining Area
    • Washer
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Terrace
    • Washer
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy stunning views over the...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 bedroom Villa in Vertine, Chianti, Tuscany, Italy : ref 23872671 / 30
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2017
    We recently enjoyed staying a week in this splendidly restored mansion in the rolling hills of the Chianti area in Tuscany . The building was tastefully decorated with respect...
    Reviewed 14 June 2017
    Awesome property with modern, well stocked kitchen and bathrooms with counter space. Spotlessly clean with beautiful outdoor areas and spectacular views. Our hostess Caterina...
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    About this property
    Independent villa, surrounded by olive groves and vineyards; the villa is reachable by passing through the historical Hamlet of Vertine. We do not recommend the use of a van and minibus. Villa Vertine is only 2.5 km from Gaiole in Chianti, in the real heart of Chianti Classico, perfect starting...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Gaiole1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Balcony
    • Washer
    • Wi-Fi
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2013
    We had a wonderful 10 day stay in Villa Gaiole. The villa is located in a small residential area, a short stroll from the main hub of the quaint village of Gaiole. The town...
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    About this property
    Beautiful Family Villa in Borgo di Gaiole, surrounded by the Chianti hills covered in vineyards and olive groves, just a 100 meters walk from the quiet village of Gaiole in Chianti, a typical Tuscan hamlet with restaurants, shops and amenities, an ideally located between Siena and...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 bedroom Villa in Gaiole in Chianti, Tuscany Chianti, Italy : ref 23961231 / 24
    (1)Average
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Excellent villa with 5 bedrooms good kitchen,pool and rooms for social activitiesPositive proiperties: near the nice town of Gaiole with vineyards and castles nearby. Only a...
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    About this property
    Outside Description: Beautiful country house Villa Il Brolio , from the 12nd century, renovated. 6 km from the centre of Gaiole, in the countryside. Private: property 3 000 m2, terraced garden, swimming pool (4 x 10 m, depth 120 - 150 cm, 01.04.-07.10.). Outdoor shower, terrace, garden furniture....
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This very special property is located on the edge of Castello di San Donato in Perano (Chianti), a beautiful hamlet which has recently been restored to such a high standard that it was awarded by the International Property Awards 2006. Cavalcanti’s position allows the guests to enjoy unusual...
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    Location Information
    53017, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 61 / 25
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 January 2016
    It 'was a wonderful holiday. The apartment is just perfect. Super clean and really welcoming. With a magnificent view. The location is perfect to visit the whole area of Chianti...
    Reviewed 10 January 2016
    We stayed at the apartment for a week in july. It is close to the small village Gaiole (5 min walk) with a small food market and a couple of restaurants. The pool is very nice...
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    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Podere Pretaccione is a 1000 year old Tuscan building that was once the home of itinerant priests. Located in the heart of the Chianti Classico wine region, Pretaccione provides a restful, rural setting just 30 minutes from historic Siena and 10 minutes to Gaiole in Chianti, home of the L’Eroica...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Torre di Cancelli - luxury villa in Chianti!1 / 30
    (1)Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Satellite TV
    • Parking
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2016
    This Gorgeous villa exceeded all my expectations for a perfect family summer vacation in Italy. The home is a perfect marriage of ancient charm and modern conveniences. The...
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    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Le Diacce1 / 17
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Central Heating
    • Wi-Fi
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2016
    We stayed at Le Diacce for a week with our adult sons and their partners. This was an absolutely idyllic stay! Franca is the best hostess ever! She makes you feel so welcome...
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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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Terrace
    • Shared Garden
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Washer
    • Central Heating
    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very ancient farmhouse dating back to year 1000 making part of a typical and charming chianti classico wine producing area with olive trees and wooded hills in a prestigious location between Florence and Siena, near the capital ot ghe vintage bycicle contest Eroica, Gaiole in Chianti, with pool,...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Parking
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cosy and comfortable 2-bedroom apartment is ideally located in the hamlet and develops on one level on the first floor. There is independent access via an external staircase and views over the village and countryside. It avails of a private terraced garden outside the main entrance with...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Satellite TV
    • Washer
    • Central Heating
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Ciaccheri1 / 13
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    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. Outside a portion of an equipped courtyard is available for the exclusive use of the guests...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Parking
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Il Gufo n°1', 9-room apartment 180 m2 on 2 levels on 1st floor. Comfortable and wooden furniture furnishings: living/dining room with open-hearth fireplace. Small living room with 1 double sofabed (160 cm), satellite TV. 1 double bedroom. Kitchenette (4 hot plates, dishwasher, microwave)....
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 7 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy and nice Villa is a restored hay barn that lays on the hillside 300 meters walk (or 2 km drive) from the exquisite village of Lecchi in the middle of Chianti. The Villa is on two levels that are joined by external stairs. The ground floor entrance is from the lower terrace and enters the...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful and tastefully furnished 1 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful Siena<BR>The apartment...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful and tastefully furnished 2 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful Siena<BR>The apartment...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Il Mulinaccio1 / 12
    (1)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Parking
    • Private Garden
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 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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    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    5 Bedrooms, 8 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EXTERNAL DESCRIPTION Castello di Gaiole is one of many castles that were constructed during the medieval period of the Lega del Chianti, the Florentino's last bastion on the border with Siena. It is situated in a medieval hamlet, made of white stone "alberese" typical of the area and built around...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 8 Bathrooms, Sleeps 10
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