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Gaiole in Chianti Vacation Rentals

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    Travelers to Gaiole in Chianti are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    All 203 Rentals in Gaiole in Chianti
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    Cottage with pool for 2 couples - Interesting promotions for September weeks..1 / 36
    (14)Very good
    2 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS1 / 24
    (39)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool1 / 20
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Washer
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 24, 2017
    We had a lovely holiday in Micks apartment in Borgo Gaiole. The Borgo is a wonderful complex, built in ancient style. It has a nice atmosphere to it. The surroundings in chianti...
    Reviewed August 8, 2015
    This apartment is great for a family of 4. We had a wonderful stay in Gaiole. The village is 5 min by walk and the pool was really appreciate by the children. Garage spot (small...
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    About this property
    Casa Felice is 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...
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Experience the 'Chiantishire' at villa LisiDor - September is at 25% OFF!1 / 70
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 5, 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 October 21, 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 ... SEPTEMBER PROMOTION 25% OFF! It's harvest time! And September weeks are at 2.900 Euro instead of 3.900 Euro! PLEASE BE AWARE!: We can only accept WEEKLY bookings with change-over day on SATURDAYS: so 7...
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    53010, Gaiole in Chianti, Province of Siena
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Hilltop Poolside 2 Bedroom Villa in Chianti1 / 27
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Hot Tub
    • Internet Access
    • Outdoor Dining Area
    • Central Heating
    • Cable/satellite TV
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2015
    We spent 15 days at la Pieve Marsina. The host Gabriele, the old-stone house on a hilltop, the swimming pool, and the countryside (we were surrounded by Chianti vineyard) were...
    Reviewed August 1, 2014
    With my husband and 2 daughters we had a great vacation in Tuscany.The oldest is 17 and the youngest is 13 year old. We had a split level appartement with authentic...
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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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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borgo di Gaiole is located in the heart of Chianti Senese, a known area all over the world for its excellent gourmet products. The apartments are inside the ancient but recently restructured Borgo, which enjoys a magnificent view on the surrounding hills. At guests' disposal, for relaxing and...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borgo di Gaiole is located in the heart of Chianti Senese, a known area all over the world for its excellent gourmet products. The apartments are inside the ancient but recently restructured Borgo, which enjoys a magnificent view on the surrounding hills. At guests' disposal, for relaxing and...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Patio
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Parking
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    LA VACANZA NEL CUORE DEL CHIANTI1 / 21
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Children's Pool
    • Grill
    • Mountain Views
    • Wi-Fi
    • Central Heating
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 4 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Central Heating
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borgo di Gaiole is located in the heart of Chianti Senese, a known area all over the world for its excellent gourmet products. The apartments are inside the ancient but recently restructured Borgo, which enjoys a magnificent view on the surrounding hills. At guests' disposal, for relaxing and...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Balcony
    • Terrace
    • Internet Access
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    UNA VACANZA DA SOGNO1 / 14
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Wi-Fi
    • Private Yard
    • Parking
    • DVD Player
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Parking
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 20, 2017
    A great place to stay. Very central in the Chianti region and very quiet and a little isolated which suited us very well indeed
    Reviewed September 5, 2016
    Our stay at the Villa was as expected. The location is isolated which we were looking for and most definitely in a beautiful and tranquil setting. Both Marcello and Sarah were...
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    About this property
    Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and nature walks on foot or by...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    • Central Heating
    • Parking
    • Private Yard
    • Patio
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    Casacorvo Minore *2018 Late Summer Discounts*:  *Exclusive EV Point Included*1 / 22
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2018
    Beautiful apartment with swimming pool in Gaiole Di Chianti.We had a great time A short distance to montevarchi were we took the train to Florence and then to Venice which we...
    Reviewed August 11, 2018
    Just what we needed. A comfortable apartment for 2 with outdoor terrace.The complex is modern but built in Tuscan style. Walking distance albeit up and down a steep hill to...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Secure Parking
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bio Agriturismo Reggioli - Stanza dell'Ortolano1 / 4
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
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    Pet friendly
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    Smoking allowed
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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 Yard
    • Cable/satellite TV
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    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 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
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Terrace
    • Washer
    • Grill
    • Private Yard
    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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    Villa Gaiole1 / 33
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Balcony
    • Washer
    • Wi-Fi
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 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 Florence. It is...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Casacorvo Maggiore: *2018 Easter Discounts: Exclusive EV Point Included*1 / 23
    (14)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
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2018
    We stayed in Casacorvo Maggiore for ten days at the end of July and found it to be the ideal base for relaxing and enjoying the beautiful weather and scenery and also for...
    Reviewed September 2, 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...
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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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    Location Information
    53013 SI, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Shared Indoor Pool
    • Cable/satellite TV
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    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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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Le Pratola1 / 47
    (5)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    • Housekeeping Included
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2016
    absolutely every aspect of our stay at Le Pratola was perfect: the villa itself, the staff, the owner, the location. This is how we all should live....like kings and queens...
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    About this property
    Set on a hilltop in Chianti, villa Le Pratola offers views in every direction and something for every member of the family. Kids will love the pool and games room, while adults will appreciate the proximity to Siena and Florence. Five air-conditioned bedroom suites and nearly five acres of gardens...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked in the vineyards in the heart of Chianti Classico, the restored farmhouse is a magical and luxurious Tuscan experience. Stomp your own grapes, walk to a Medieval castle, wake up to farm fresh eggs. Why It’s Special: Designer elegance, restored 16th-Century architecture and breathtaking...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/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 The apartment is...
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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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    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
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 30, 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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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Terrace
    • Secure Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 in the...
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    Location Information
    53030, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 10, 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 January 10, 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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    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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    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cavalcanti1 / 13
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Housekeeping Included
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 11, 2015
    Cavalcanti was very nicely appointed. Two real master suites with en-suite baths and one double room with twin beds and en-suite bath at the opposite end of the house. The...
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    About this property
    Tucked between the villages of Gaiole and Radda in Chianti in the heart of Tuscany, Cavalcanti offers the privacy of a villa and the amenities of a larger estate. As part of the restored hamlet of Castello di San Donato in Perano, the three-bedroom property is surrounded by vineyards, a...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Children's Pool
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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 Yard
    • Secure Parking
    • Hot Tub
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 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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    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 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
    • Parking
    • Central Heating
    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, 3 Bathrooms, Sleeps 7
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    Casa Giardino1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Private Yard
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Balcony
    • Secure Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 21, 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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    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...
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    Location Information
    53030, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Fienile con vista sui vigneti1 / 28
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Private Yard
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 13, 2018
    We spent a wonderful long weekend in Gaiole, hung out by the fireplace, went for long walks and to pretty little Siena. We had amazing Italian food, friendly neighbors and at...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    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...
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    53013, Nusenna, Gaiole in Chianti
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Central Heating
    • Private Yard
    • Washer
    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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    castello in Chianti  conte1 / 23
    (2)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 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 November 9, 2015
    One of the reasons we chose the place was because although remote, it had a restaurant so, with a small child, this would make things more convenient. When arrived unfortunately...
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    About this property
    This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday apartments, where visitors can...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cosy and comfortable first-floor 2-bedroom apartment sits overlooking the rest of the hamlet, also with views over the pool. The entrance leads into the spacious living room where crisscrossed terracotta tiling runs seamlessly throughout the apartment, whilst Chestnut beams are highlighted...
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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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/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 The apartment is...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DEAR TRAVELER, PLEASE KINDLY NOTE: The rental price includes: final cleaning; electricity; parking; Wi-Fi Internet connection; linens and towels. Available for a fee, if desired:heating (when needed) EUR 20.00/day;pets EUR 15.00. Casa Refolo A is a characteristic two-story apartment that is part...
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    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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