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Luxury Rentals in San Casciano in Val di Pesa, Italy

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$3,749
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1 / 81
18 Bedrooms, 17 Bathrooms, Sleeps 65
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$11,191
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1 / 6
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8 Bedrooms, 18 Bathrooms, Sleeps 16
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$1,455
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1 / 25
11 Bedrooms, 10 Bathrooms, Sleeps 20
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$1,350
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1 / 6
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9 Bedrooms, 1 Bathroom, Sleeps 20
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$9,087
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1 / 57
11 Bedrooms, 10 Bathrooms, Sleeps 22
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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About this property
Borgo Casciano offers a terrific setting for a large gathering or for smaller groups.  The entire villa is complete with five apartments that accommodate 22 guests and can be rented as one exclusive dwelling for a large group. The apartments can also be rented separately. The location of Borgo... View all property information
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$8,601
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1 / 24
7 Bedrooms, 4 Bathrooms, Sleeps 14
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  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
  • Wi-Fi
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Tuscan country farmhouse near Florence to rent – Casolare del Chianti is a traditional refurbished farmhouse sitting on a large rural estate, ideally located in the popular Chianti region, between Florence and San Gimignano. This is quintessential Tuscany, whose Classic wines and idyllic landscapes... View all property information
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$8,393
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1 / 23
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11 Bedrooms, 9 Bathrooms, Sleeps 20
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Originally a Medieval feudal castle, the property was converted to a villa between 1450 and 1500. As you would expect, it is steeped in history and is a fascinating place to spend a holiday in this wonderful part of Tuscany. The property is divided into two main sections - The Conventino and Torre... View all property information
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$1,183
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1 / 23
11 Bedrooms, 9 Bathrooms, Sleeps 20
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  • Dishwasher
  • Fireplace
  • Grill
  • Satellite TV
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a fabulous Tuscan villa sleeping between 15 and 20 people. Originally a Medieval feudal castle, the property was converted to a villa between 1450 and 1500. As you would expect, it is steeped in history and is a fascinating place to spend a holiday in this wonderful part of Tuscany. The... View all property information
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$7,722
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1 / 48
Montefiridolfi
5 Bedrooms, 6 Bathrooms, Sleeps 10
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  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Surrounded by vineyards and olive groves, Casale Classico is perfect for five couples or an extended family, and the location couldn't be better. Located in the heart of Tuscany's Chianti Classico region and set on an idyllic hillside just 15 minutes from Florence (18 km) and less than an hour from... View all property information
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$7,705
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1 / 43
6 Bedrooms, 6 Bathrooms, Sleeps 17
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
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  • ?
About this property
Located in the heart of Tuscany's Chianti region, Casa Matteo is an outstanding villa with stunning views over characteristic olive groves, vineyards, forests and country estates.  This spacious independent country house, originally a small monastery, has five bedrooms with five en suite bathrooms... View all property information
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$1,000
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1 / 26
4 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Internet Access
  • Private Outdoor...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
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About this property
Casa Poggio is a farmhouse located in a beautiful estate, 100 m from a charming medieval village. Guests can enjoy outstanding views of the Chianti hills and olive groves from all its rooms. The house is friendly, luminous and decorated with antique furniture, kilim carpets and every modern... View all property information
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$753
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1 / 11
8 Bedrooms, 8 Bathrooms, Sleeps 16
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  • Dishwasher
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
This delightful farmhouse for 16 in a grand estate would make the ideal accommodation for a wide variety of guests- a family or group on holiday, attendees at a conference, or guests at one of the special events or weddings held at the villa. Additional amenities include: accessibility wheelchair... View all property information
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$4,980
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1 / 24
8 Bedrooms, 9 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The La Corte estate stretches out over a hillside covered with vineyards, olive trees and woodland. It is set in the very heart of Chianti near the main road from Florence to Siena, only 16 km south of Florence. This lovely estate on the western fringe of Chianti is owned by one of Italy's oldest... View all property information
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5 of 5 stars Reviewed November 15, 2011
This was a wonderful villa. First, where can you find a villa where each bedroom had its own bathroom? All of our friends were extremely happy with the accommodations. Great...
5 of 5 stars Reviewed October 2, 2011
We had 13 people at the villa for two weeks. We could not have been more pleased. The villa bathrooms have all been updated and were extremely great shape considering we were in...
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$4,481
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1 / 70
Montefiridolfi
4 Bedrooms, 4 Bathrooms, Sleeps 11
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Amenities & Details
  • Dishwasher
  • Gym
  • Private Outdoor...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
With traditional furnishings, a private swimming pool, and a fantastic location just south of Florence, this Tuscan villa for rent is right out of your Italian fantasies! This is not a bare hotel; this is a home, a Tuscany villa near Florence filled with character and elegance. From this vacation... View all property information
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$4,128
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1 / 28
5 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Dishwasher
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Surrounded by the marvelous Chianti hills, this ample and traditional farmhouse sleeps up to 10 people. A large swimming pool, several bedrooms and bathrooms, and a cozy atmosphere for those who long to experience Tuscan life in the countryside. Additional amenities include: heating. View all property information
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$4,073
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1 / 16
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5 Bedrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Fireplace
  • Pool Table
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
About our villas in italy Mezzola is a typical stone-built Tuscan farmhouse, located on an estate producing Chianti wine, only 1 kilometre from Cerbaia and 18 kilometres from the centre of Florence. Until a few years ago, it was the home of the owner, an antique dealer, who restored and furnished... View all property information
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$548
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1 / 17
6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
The historic Casa Erta, acquired from the Machiavelli family, together with the other farm houses on the property, have been restored with great care to their original form. Casa Erta is positioned in a pristine location amid cypresses, olive groves and vineyards, with views that have escaped the... View all property information
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$548
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1 / 16
6 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
The historic Casa Corza, belonged to the legendary Cavalcanti and Niccolini families, Florentine nobility and together with the other farm houses on the property, have been restored with great care to their original form. Casa Corza is positioned in a pristine location amid cypresses, olive... View all property information
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$3,766
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1 / 20
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Balcony
  • Dishwasher
  • Grill
  • Private Outdoor...
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Originally a farmhouse owned by the Medici family, and dating back to the early fifteenth century. Villa Il Portico is perfectly positioned between Florence and Siena. This large holiday rental property was originally a farmhouse owned by the Medici family and dates back to the early fifteenth... View all property information
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5 of 5 stars Reviewed August 24, 2014
Villa il Portico, a.k.a. Montepaldi a.k.a.Fume - whichever is the proper name - was a slice of paradise and a welcome haven during some unexpected vacation crises. I traveled to...
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From
$3,581
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1 / 13
4 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Dishwasher
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The stone walls and the ample spaces in this ancient villa in Tuscany welcomes its guests and comforts them with modern amenities, a warm atmosphere and enchanting views of the surroundings. Additional amenities include: pets considered, heating. View all property information
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From
$3,580
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1 / 44
4 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Dishwasher
  • Internet Access
  • Private Outdoor...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Ancient farmhouse surrounded by olive groves and terraced areas and situated inside the Castello di Bibbione estate in the Chianti area. The castle dates back to the early 11th century, whereas the stone-built houses of the hamlet date back to the early 13th century. The villa rental was... View all property information
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From
$505
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1 / 20
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Villa Il Turco is an elegant, aristocratic, sixteenth-century country estate which once belonged to a noble family named Rosselli Del Turco. Enjoy noble splendour in this gracious antique villa which is both close to Florence and immersed in tranquillity. Complete with vaulted ceilings downstairs... View all property information
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From
$3,531
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1 / 21
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Private Outdoor...
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Enjoy noble splendor in this gracious antique villa which is both close to Florence and immersed in tranquility. Villa Il Turco is an elegant, aristocratic, sixteenth-century country estate which once belonged to a noble family named Rosselli Del Turco. Complete with vaulted ceilings downstairs... View all property information
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From
$3,509
Per Week
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1 / 42
5 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Splendid and characteristic Chianti villa (400 m2) that dates back to the early 15th century. Once belonging to the Medici family, it is situated in a small valley amid the Chianti hills and has been skilfully restored and transformed into a cosy country house. The villa rental is comfortable and... View all property information
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From
$3,240
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1 / 37
6 Bedrooms, 7 Bathrooms, Sleeps 15
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Looking to explore the Chianti region of Tuscany with all the comforts of home—and more? This estate features two private villas for rent in Tuscany, two swimming pools, sprawling grounds and all the amenities indoors. How is this possible? One of the owners of this accommodation in Tuscany—with... View all property information
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From
$403
Per Night
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1 / 12
6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Dishwasher
  • Grill
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Characteristic Tuscan-style Chianti villa, independent and secluded, located in the heart of Tuscany, in the Chianti Classico region, a few kilometers from San Casciano Val di Pesa. The villa rental is surrounded by the Tuscan hills, olive groves and vineyards, in a quiet area that offers many... View all property information
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From
$400
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1 / 14
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6 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: Apr 21 - Apr 25 : Tuesday, Wednesday, Thursday, Friday and Saturday check-out required.; May 24 - May 30 : Sunday, Monday, Tuesday, Wednesday, Thursday, Friday and Saturday check-out required.; Jun 28 - Jul 04 : Sunday, Monday, Tuesday,... View all property information
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3 of 5 stars Reviewed June 17, 2014
I rented Casa Bulleri for one month to celebrate my 50th birthday. It was the perfect size to host 40+ friends and family over the month that had traveled to join the celebration...
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From
$388
Per Night
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1 / 35
5 Bedrooms, 3 Bathrooms, Sleeps 9
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Archipettoli is a magnificent country estate, situated between Florence and Siena, with 14 acres of private landscaped gardens is uniquely located as if perched on top of the hill in the middle of the typical Tuscan countryside with its rows of vineyards and groves of olive trees. From its location... View all property information
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4 of 5 stars Reviewed September 26, 2014
We recently spent a week in Archipettoli with a family party of seven. The villa was everything that we hoped it would be: traditional rural Tuscan ambience, stunning position...
5 of 5 stars Reviewed August 15, 2013
We stayed at Archipettoli with friends and young children and had the most wonderful holiday we could expect. They looked after us very well, organising cots and highchairs and...
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From
$376
Per Night
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1 / 21
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4 Bedrooms, 5 Bathrooms, Sleeps 8
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From
$2,516
Per Week
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1 / 36
5 Bedrooms, 4 Bathrooms, Sleeps 12
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Villa Pisignano is a characteristic Tuscan country house (“Leopold style”) situated on the Florentine hills, approx. 3 kilometers away from the small town of San Casciano Val di Pesa. This villa, surrounded by beautiful olive groves and vineyards, is in quiet and panoramic location. The villa... View all property information
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From
$355
Per Night
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1 / 22
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Fireplace
  • Internet Access
  • Private Outdoor...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Colorful Artsy 4 Bedroom Villa Feel at home at this colorful, bright, spacious villa - perfect for relaxing getaways in beautiful Tuscany. This bright, colorful villa offers you the chance get away from busy life and spend some time surrounded by the beautiful Tuscan scenery.The villa is very... View all property information
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Suitability

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