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Holiday Rentals and Villas in San Casciano in Val di Pesa, Italy

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    Travellers to San Casciano in Val di Pesa are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 12
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
    1 / 28
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
    1 / 40
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    700 yr-old FarmHouse renovated to Western standards.Sits on top of a gorgeous pano hillside, saltpool,a/c.Directly off Chianti Classico wine road.5 min walk to Le Corti Winery.17 mins drive to Florence, Piazza Michelangelo. PerfectLocation! Stunning! It is considered a two bedroom home but it is... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 13
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
    1 / 23
    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is a 4 bedroom villa located in the Chianti Classico region of Tuscany, just 20 minutes from Central Florence. It is a perfect base for larger families or groups of friends who are looking for the privacy that a villa offers. The property enjoys use of a circular swimming pool, surrounded by... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 32
    5 of 5 stars (2) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
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    1 / 16
    5 of 5 stars (1) Excellent
    Mercatale di Val di Pesa
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Atelier 2 is the smaller of our Atelier Apartments. 80 m in the Chianti Classico. The apartment has a tastefully decorated double bedroom and a very large marble bathroom. The large Atelier of the famous Dutch painter Karel Apple (member of COBRA group) who owned the estate Villa Licia and worked... View all property information
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    Mercatale di Val di Pesa, San Casciano in Val di Pesa
    1 / 6
    5 of 5 stars (5) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    About this property
    The old family farmhouse opens onto the living room-kitchen with the traditional Tuscan hearth. The graceful east-facing terrace is perfect for a sunny breakfast among the sounds of the countryside and chirping birds. (90 sq. meters - sleeps 6+2) Ground floor: kitchen with stove, dishwasher,... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 26
    5 of 5 stars (32) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Mountain Views
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    About this property
    See what the experts say about us! Trip Advisor-FlipKey Award of Excellence, Conde Nast Traveler Magazine Italy Experience Maker award, Travel & Leisure Magazine Italy All-Star award, Better Business Bureau A+ perfect rating, SlowTravel Preferred, Vacation Rental Managers Association professional.... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 90
    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    The house is situated in the heart of Chianti in a typical hamlet dating from the 1400's surrounded by vineyards and olive groves.The house is only 25km from Florence and 35km from Sienna. In 2010 the property was completely renovated. The house is split over two levels. On the ground floor there... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 17
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Porch
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    • Satellite TV
    • Outdoor Dining Area
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    • x
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    • x
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    San Casciano in Val di Pesa, Province of Florence
    1 / 20
    Mercatale di Val di Pesa
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Balcony
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    • DVD Player
    • Children's Pool
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    • Pet-friendly
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    • x
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    • x
    About this property
    Welcome to Villetta. This is a freestanding smaller type of Villa with its private garden of 3000 m2 ....in the Chianti Classico. With spacious living and tastefully decorated. We offer 2 double and 1 single bedroom. Sofabed for 2 persons. 2 marble bathrooms. Villetta is close to the old... View all property information
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    Mercatale di Val di Pesa, San Casciano in Val di Pesa
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    The Torriano is located at the highest point of the scenic road that leads to the Castle of Bibbione Montefiridolfi. The characteristic landscape of Chianti and sunsets that you enjoy are unforgettable. <BR><BR>The house is surrounded by a beautiful lawn with fruit trees and olive trees and the... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villa Gentile is a pleasant and spacious ancient tuscan country house made of stone. It sleeps eight people. From Villa Gentile you will enjoy a characteristic view of the Chianti hills and of the surrounding countryside. Villa Gentile is 300 square meters (3230 square feet). It features a private... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 19
    5 of 5 stars (1) Excellent
    Mercatale di Val di Pesa
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    About this property
    Casa delle Rose is a wonderful villa with its private rose garden,fountain and private traverin swimming pool. In Chianti Classico You find here a fine living room, 5 tastefully decorated bedrooms with double beds (200x200cm), 4 marble bathrooms.....a very complete Tuscan kitchen and dining area.... View all property information
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    Mercatale di Val di Pesa, San Casciano in Val di Pesa
    1 / 24
    Montefiridolfi
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    In the heart of Chianti, halfway between Florence and Siena<br>The farmhouse I Greppi Di Silli located 300 mt above sea level. rises and looks out over a green valley, surrounded on all sides by cultivated hills covered in olive groves and vineyards.<br><br>Alongside the borgo, in the middle of the... View all property information
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    Montefiridolfi, San Casciano in Val di Pesa
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    1 / 20
    5 of 5 stars (2) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 9
    Montefiridolfi
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    The Fattoria Montignana is made up of well furnished apartments and a relaxing informal garden. In total, Fattoria Montignana offers 11 apartments which have been carefully restored and furnished following the typical Tuscan style. It is located where the vines of the vineyards grow closer... View all property information
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    Montefiridolfi, San Casciano in Val di Pesa
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    A charming, elegantly furnished, well equipped villa. A perfect base from which to tour Florence and the Chianti. Owned by a local family with extensive vineyards and olive groves, this (totally renovated) farmhouse is set in a secluded location and offers private, very comfortable and peaceful... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 76
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    These two family apartments are equipped with antique furniture and beautiful carpets, and they boast a very traditional atmosphere. One of them is located on the ground floor, and the other one is on the first floor, and they both afford a kitchen area, a living room with sofa-bed, private... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    These vacation homes for 6 people brims over with the style of Chianti. To enjoy sipping a glass of wine outdoors, the apartments have a large porch and its garden area. These apartments affords a living room with a fireplace. Its fully fitted kitchen features its dining area. Its can host up to 6... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • ?
    • ?
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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. Borgo Casciano rents from... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
    1 / 18
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Hot Tub
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    San Casciano in Val di Pesa, Province of Florence
    1 / 73
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    These four large apartments are between 79 and 119sqm big, and they sleep up to 6 people each. They all boast antique furniture and beautiful carpets, fully equipped kitchens and bathrooms with Jacuzzi.One of them is located on a first floor, so it features a lovely terrace with table and chairs,... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 95
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
    1 / 30
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Description: A farmhouse near to a village 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... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 27
    11 Bedrooms, 10 Bathrooms, Sleeps 15 | Quick View
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    • Balcony
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    • Pet-friendly
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    About this property
    In the heart of the Chianti region, 15 minutes drive from Florence, stands Castello Buondelmonti set on a hillside overlooking the valley of the river Pesa. This extraordinary example of Tuscan medieval castle was built, on the foundations of a Roman Settlement, in the 10th Century by the... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 39
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Furnishings of Chianti air and ancient walls dating back to the Middle Ages are enchanting features of these vacation homes for 4 people. Guests can relish a sunset while tasting some regional wine in the garden or porch which the apartment affords. These apartments have a spacious living room and... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 25
    11 Bedrooms, 9 Bathrooms, Sleeps 26 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • 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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    San Casciano in Val di Pesa, Province of Florence
    1 / 23
    11 Bedrooms, 9 Bathrooms, Sleeps 20 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • 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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    San Casciano in Val di Pesa, Province of Florence
    1 / 10
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Great room with bathroom, in the heart of Chianti. Terracotta floor and roof with exposed beams. Antique furniture, typical toscana.Parcheggio private.<BR>At about 20 km from Florence and 40 km from Siena, the farmhouse's position is perfect to reach the most beautiful, cultural and gastronomic... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    San Casciano in Val di Pesa, Province of Florence
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
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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. Borgo Casciano 5 rents... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 37
    5 of 5 stars (43) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Secure Parking
    • Mountain Views
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    About this property
    "Le Massucce" is located in the heart of Chianti in San Casciano Val di Pesa, a medieval region renowned for its good oil and wine. This perfect location, in between Florence (15 km to the North) and Siena (30 km to the South), is ideal for exploring Tuscany and the cultural centres like Florence... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 30
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    In the ancient hamlet that surrounds the Bibbione Castle ,12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills in front of San... View all property information
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    San Casciano in Val di Pesa, Province of Florence
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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. Borgo Casciano 1 rents... View all property information
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 13
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Shared Garden
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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. The stone walls and the ample spaces in this ancient villa in Tuscany welcomes its guests and comforts them... View all property information
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor...
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    This is an independent villa, covering 200 square metres, and extending over two storeys, plus the traditional Tuscan dovecot on its rooftop, now converted into a luxurious bathroom. Although recently fully renovated, the interiors nonetheless retain many typical characteristics of 19th century... View all property information
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 23
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
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    • Secure Parking
    • Shared Outdoor Pool...
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This small apartment is part of a country house in a small hamlet situated near the medieval village of San Casciano V.P. right in the core of the well renowed area of Florentine Chianti, no more than 20 km far from the center of Florence. The space The aparment (2pax+2) is about 50 sqm., The... View all property information
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 24
    5 of 5 stars (5) Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Washer
    • Grill
    • Parking
    • Internet Access
    • Satellite TV
    • Shared Garden
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    A farmhouse near to a village 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... View all property information
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 16
    11 Bedrooms, 10 Bathrooms, Sleeps 22 | Quick View
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    Amenities & Details
    • Shared Outdoor Pool...
    • Grill
    • Internet Access
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    (Minimum of one week rental required) Unit 1 sleeps six guests and is located in the large building, (the former oil mill). The ground floor consists of a large, fully equipped kitchen (stove, oven, fridge/freezer, microwave, toaster, coffee maker), living room with open fireplace, and a bathroom... View all property information
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 21
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • Parking
    • Private Outdoor...
    • Private Garden
    • Central Heating
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 14
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    The historic Casa Gina, acquired from the Machiavelli family, together with the other farm houses on the property, has been restored with great care to its original form. Casa Gina is positioned in a pristine location amid cypresses, olive groves and vineyards, with views that have escaped the... View all property information
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 26
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    San Casciano in Val di Pesa, Province of Florence
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Payment Protection
    Amenities & Details
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    San Casciano in Val di Pesa, Province of Florence