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Luxury Rentals in San Casciano in Val di Pesa, Italy

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    Travelers to San Casciano in Val di Pesa are booking August dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $14,018
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    1 / 80
    18 Bedrooms / 17 Bathrooms / Sleeps 65
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    $10,920
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    1 / 18
    11 Bedrooms / 10 Bathrooms / Sleeps 22
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    $1,444
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    11 Bedrooms / 10 Bathrooms / Sleeps 20
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    $9,400
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    1 / 20
    6 Bedrooms / 7 Bathrooms / Sleeps 10
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    Amenities & Details
    • Satellite TV
    • Dryer
    • Hot Tub
    • Fireplace
    • Air Conditioning
    • Grill
    • Refrigerator
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    15% discount for the week of June 6-13, 2015 (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. On the ground floor there is a spacious dining area with a table for 12 people. On the left of the dining room there is a nice living... View all property information
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    55024, San Casciano in Val di Pesa, Province of Florence
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    $9,018
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    1 / 57
    11 Bedrooms / 10 Bathrooms / Sleeps 22
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    • Grill
    • Wi-Fi
    • Private Outdoor...
    • Satellite TV
    • Dryer
    • Air Conditioning
    • Microwave
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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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    50026, San Casciano in Val di Pesa, Province of Florence
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    $8,674
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    1 / 24
    7 Bedrooms / 4 Bathrooms / Sleeps 14
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    • Air Conditioning
    • Satellite TV
    • Refrigerator
    • Grill
    • DVD Player
    • Wi-Fi
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • 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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    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $8,443
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    1 / 31
    8 Bedrooms / 7 Bathrooms / Sleeps 15
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    Amenities & Details
    • Dishwasher
    • Parking
    • Central Heating
    • Satellite TV
    • Washer
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    A typical example of a Tuscan medieval castle, dating to the 12th century, built by the architect Buondelmonti as a fortification to defend the feudal possessions. Transformed into a country villa in 1520, with large decorated rooms and elegant arcades, the castle is perched on a steep hill... View all property information
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    50026, San Casciano in Val di Pesa, Province of Florence
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    $8,330
    / Week
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    1 / 25
    11 Bedrooms / 9 Bathrooms / Sleeps 20
    traveler have booked this property
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    • Horse Riding Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $1,174
    / Night
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    1 / 23
    11 Bedrooms / 9 Bathrooms / Sleeps 20
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Stove
    • Fireplace
    • Refrigerator
    • Grill
    • Satellite TV
    • Central Heating
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $7,663
    / Week
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    1 / 48
    5 of 5 stars (2) Excellent
    Montefiridolfi
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Refrigerator
    • DVD Player
    • Dryer
    • Grill
    • Stereo System
    • Washer
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • 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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    Location Information
    Montefiridolfi, San Casciano in Val di Pesa
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    From
    $7,647
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    1 / 43
    6 Bedrooms / 6 Bathrooms / Sleeps 17
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Dishwasher
    • Grill
    • Dryer
    • Washer
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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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    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $747
    / Night
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    1 / 11
    8 Bedrooms / 8 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • Shared Yard
    • Refrigerator
    • Private Outdoor...
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $747
    / Night
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    1 / 15
    8 Bedrooms / 8 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Grill
    • Hairdryer
    • Private Outdoor...
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ExteriorVilla Reale is one of the farmhouses found on a grand agricultural estate where Chianti Classico wine is produced from the 50 hectares of vineyards, along with organic olive oil.Throughout the year, guided tours of the cellars, oil mill and orchard are offered, with demonstrations of the... View all property information
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    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $4,942
    / Week
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    1 / 24
    5 of 5 stars (5) Excellent
    8 Bedrooms / 9 Bathrooms / Sleeps 12
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Stereo System
    • Washer
    • Grill
    • Internet Access
    • Satellite TV
    • Stove
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • 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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    San Casciano in Val di Pesa, Province of Florence
    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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    From
    $4,700
    / Week
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    1 / 14
    6 Bedrooms / 7 Bathrooms / Sleeps 11
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • Fireplace
    • Washer
    • Refrigerator
    • Stove
    • Grill
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. This country estate is composed of several buildings of historical and artistic importance, and the most beautiful is the main house with its typical Tuscan architecture. This... View all property information
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    Location Information
    San Casciano in Val di Pesa, Province of Florence
    From
    $4,481
    / Week
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    1 / 70
    5 of 5 stars (1) Excellent
    Montefiridolfi
    4 Bedrooms / 4 Bathrooms / Sleeps 11
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Washer
    • Dishwasher
    • Hairdryer
    • Stove
    • Central Heating
    • TV
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • 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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    50020, Montefiridolfi, San Casciano in Val di Pesa
    From
    $619
    / Night
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    1 / 35
    4.5 of 5 stars (8) Very good
    6 Bedrooms / 4 Bathrooms / Sleeps 11
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Horse Riding Nearby
    • Private Outdoor...
    • Satellite TV
    • There Are Tennis...
    • Stereo System
    • Wi-Fi
    • Central Heating
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    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
    $4,097
    / Week
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    1 / 28
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Dishwasher
    • Shared Yard
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • 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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $4,097
    / Week
    View Details
    1 / 28
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Dishwasher
    • Grill
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ExteriorsThis traditional and splendid villa in Tuscany is situated amidst the enchanting hills of Chianti, with their different shades of green and lovely mild climate. The Tuscan countryside is ideal for taking long walks, bike rides or daily tours, visiting olive mills and wineries.Those who... View all property information
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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $3,882
    / Week
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    1 / 21
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Wi-Fi
    • Fireplace
    • Satellite TV
    • There Are Tennis...
    • Horse Riding Nearby
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    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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    Location Information
    San Casciano in Val di Pesa, Province of Florence
    From
    $554
    / Night
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    1 / 20
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Fireplace
    • Stove
    • Private Outdoor...
    • Refrigerator
    • Washer
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    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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    Location Information
    50028, San Casciano in Val di Pesa, Province of Florence
    From
    $3,741
    / Week
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    1 / 26
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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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    Location Information
    San Casciano in Val di Pesa, Province of Florence
    From
    $3,737
    / Week
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    1 / 20
    5 of 5 stars (1) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • DVD Player
    • There Are Tennis...
    • Stereo System
    • Private Outdoor...
    • Playground
    • Satellite TV
    • Wi-Fi
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    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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    San Casciano in Val di Pesa, Province of Florence
    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
    $527
    / Night
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    1 / 16
    6 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Refrigerator
    • Washer
    • Fireplace
    • Shared Outdoor Pool...
    • Wi-Fi
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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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    Location Information
    San Casciano in Val di Pesa, Province of Florence
    From
    $527
    / Night
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    1 / 17
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Shared Outdoor Pool...
    • Balcony
    • Stove
    • Washer
    • DVD Player
    • Grill
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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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    Location Information
    San Casciano in Val di Pesa, Province of Florence
    From
    $3,553
    / Week
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    1 / 44
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Washer
    • Parking
    • Central Heating
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $3,554
    / Week
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    1 / 13
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Shared Yard
    • Private Outdoor...
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • 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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $3,554
    / Week
    View Details
    1 / 18
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Dishwasher
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ExteriorsThis villa's ideal location allows its guests to visit very famous cities in the Tuscan region and which have become a must-see for every tourist in Italy. The magical city of Florence is only 18km from the property; and Siena, Pisa and Arezzo are very close as well.The countryside, the... View all property information
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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $508
    / Night
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    1 / 23
    5 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Make Inquiry
    Amenities & Details
    • Refrigerator
    • Private Outdoor...
    • Central Heating
    • There Are Tennis...
    • Wi-Fi
    • Horse Riding Nearby
    • Satellite TV
    • Stove
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Villa Guido is located just 10 miles south of Florence, within walking distance to a local Chianti village. Very quiet and peaceful, with a very large garden and a nice patio the villa benefits from its own private pool, with a shallow end perfect for the children. At the ground floor two... View all property information
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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $3,483
    / Week
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    1 / 42
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Private Outdoor...
    • Central Heating
    • Internet Access
    • Grill
    • Dishwasher
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    50026, San Casciano in Val di Pesa, Province of Florence
    From
    $3,240
    / Week
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    5 of 5 stars (2) Excellent
    6 Bedrooms / 7 Bathrooms / Sleeps 15
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • DVD Player
    • Central Heating
    • Washer
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Grill
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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
    Make Inquiry
    Location Information
    50052, San Casciano in Val di Pesa, Province of Florence