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Castiglion Fiorentino Luxury Rentals

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    Travelers to Castiglion Fiorentino are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    36 Matching Rentals in Castiglion FiorentinoView all 246 rentals
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    9 Bedrooms, 12 Bathrooms, Sleeps 18 Quick View
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    10 Bedrooms, 9 Bathrooms, Sleeps 26 Quick View
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    About this property
    Owner's description: Ancient Leopoldine villa. Beautiful Leopoldine villa situated on a panoramic position, between Arezzo and Cortona, which offers thus the possibility to easily reach the main historic and cultural cores of central Italy, such as: Firenze, Siena, Perugia, Montepulciano, Assisi,...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    Pet friendly
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    Owner's description: Pool will be open on: 04 May 2018 22:00:00 \r\nPool will be close on: 28 Sep 2018 22:00:00 \r\nUse of WiFi Internet. Welcome hamper on arrival. Towels for the swimming-pool. In the centre of Valdichiana, close to Arezzo and Cortona, at the top of a hill that dominates a...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Hot Tub
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    Pet friendly
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    Owner's description: Main Description : Vacation rental Villathis property is a lovely property (800 sq m) that includes WiFi internet, air conditioning and private pool. The property can accommodate up to 18 guests comfortably in nine bedrooms with nine bathrooms. Conveniently located in...
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    52043, Brolio, Castiglion Fiorentino
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    Owner's description: Main Description : Ancient Leopoldine villa. Beautiful Leopoldine villa situated on a panoramic position, between Arezzo and Cortona, which offers thus the possibility to easily reach the main historic and cultural cores of central Italy, such as: Firenze, Siena, Perugia,...
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    52045, Brolio, Castiglion Fiorentino
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    9 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    • Washer
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    • Private Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Magnifica is an old country residence, skillfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property. Large external pool with roman staircase and the bonus of the heated internal pool with hydromassage...
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    52043, Brolio, Castiglion Fiorentino
    Rental Home - 9 Bedrooms, 11 Bathrooms, Sleeps 24
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    9 Bedrooms, 11 Bathrooms, Sleeps 18 Quick View
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    • Cable/satellite TV
    • Private Indoor Pool
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Magnifica is an old country residence, skillfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property. Large external pool with roman staircase and the bonus of the heated internal pool with hydromassage...
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    52043, Brolio, Castiglion Fiorentino
    Rental Home - 9 Bedrooms, 11 Bathrooms, Sleeps 18
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    9 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Hot Tub
    • Air Conditioning
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    • Sauna
    • Shared Indoor Pool
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning villa is located in the heart of Valdichiana, close to Arezzo and Cortona, the relais offers the possibility to reach easily the main historical and artistic sites such as Florence, Siena, Perugia, Montepulciano, Assisi, Gubbio and lots more. Villa degli affreschi is an old country...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 9 Bedrooms, 4 Bathrooms, Sleeps 18
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    Villa Margarita, Garden Apartment with lovely Pool1 / 60
    (4)Very good
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Mountain Views
    • Washer
    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • Patio
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2018
    We stayed here this Summer, and the facilities and House itself are great. The owners are a local family and are very attentive for the needs of the guests . They made sure the...
    Reviewed August 3, 2014
    We spent a great week at the garden villa (ie the ground floor villa) in this house. It sits high above the valley with inspiring views. The villa was a great size could easily...
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    VILLA MARGARITA FOR 6 - 12 GUESTS, amazing views, Villa Margarita is the ideal spot for those seeking relaxation and the convenience to explore Tuscany. Ideal for 4 - 16 guests It provides a compelling combination of a great location and charming farmhouse style. A recent renovation offering...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Villa Castiglioni - Castiglioni Villa, Private villa and pool,  Air Conditioning   for 12 plus1 / 34
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    Reviewed September 11, 2017
    We learned about this villa from Terry Betts who manages Tuscan Charms booking company while owning his highly awarded B and B when planning a 50th anniversary trip to Tuscany...
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    About this property
    This exceptional, air conditioned. luxurious and impeccable private estate in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Extraordinary views of both the famed Montechio Castle and, the Eternal Tuscan hill town of Castiglion Fiorentino can be easily seen from...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Owner's description: In a privileged position providing windows on both the hilltop Tuscan towns of Cortona and Castiglion Fiorentino, and within a small hamlet, this property enjoys a supremely enviable location. Inside this modern villa, decorated in tasteful and contemporary hues with a...
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    52044, Castroncello, Castiglion Fiorentino
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Washer
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    Pet friendly
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    Owner's description: Outside Stunning Tuscan countryside house with beautiful views. With private pool overlooking the estate olive groves this house makes a unique holiday place to spend a holiday. Villa 'this property', detached, renovated, surrounded by trees and fields. 5 km from the centre of...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 15
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    Villa Il Ceriolo1 / 12
    (7)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    • Grill
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    • Balcony
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    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 26, 2017
    The location is not far from any of the villages in Arezzo. Cortina and Arezzo are two of the most interesting areas and they are about 30 minutes from the villa. The pool is...
    Reviewed June 18, 2015
    Amazing idyllic home in a dreamlike setting. All the comforts of a modern home, in a centuries old house. Wonderful owners that know everything to do in the area. Food...
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    About this property
    The beautiful old stone house is quite large, incorporating 4,500 sf (400 sm). It includes a total of six bedrooms and five baths, with a sleeping capacity of 13. The property includes a lovely garden with a small vineyard and numerous olive trees. Il Ceriolo is located just 5km outside the town...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Owner's description: this property - NEAR MONTEPULCIANO this property is a beautiful villa (230sqm) located in a peaceful location south of the wonderful town of Montepulciano. The villa has been built from the local stone and it boasts a lovely swimming pool (irregular shape, 14m x 7m - 90cm-2.30m...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Washer
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immersed in the green of the olive trees and woods in the peaceful hills of Tuscany, the ideal destination for those seeking a healthy and peaceful stay of relaxation and comfort, Villa Il Castello is located between the cities of Arezzo and the quiet Etruscan town of Cortona and just few minutes...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Owner's description: Villa Orzale-Arezzo Just at the border between Tuscany and Umbria, Villa Orzale is a country style villa with private swimming pool for 12 people. The area offers various cultural events like the 'Palio dei Rioni' (horse race) and with just a short drive from Arezzo you can...
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    52043, Castroncello, Castiglion Fiorentino
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    Pet friendly
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    Owner's description: 9 Bedroom Detached Villa Arezzo Villathis property is a lovely Tuscan Manor house and cottage enclosed in spacious grounds. In the hills between Arezzo and Cortona this spacious villa is comfortably furnished in country style and has an inviting atmosphere. There plenty of...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Owner's description: VILLAthis property – AREZZO AREA Villathis property is located close to the town of Castiglion Fiorentino, just 1km outside of it, reachable within a short walk where you can find many shops, restaurants, cafes, etc. Within a short driving distance, you can reach the beautiful...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    Villa Castello Roccolo - Tuscan Borgo With fabulous views, Perfect for 6 guests1 / 35
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2016
    This was our first villa booking in Tuscany for my wife and I and our grown up children who were visiting during different periods of the holiday. We booked this villa early...
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    About this property
    A fabulous Tuscan home for family and friends to enjoy Stunning views and a tranquil position - with great opportunities to explore the Tuscan area. The landscape and remains of the ancient castle dates back to the 11th century are naturally stunning and this lovely 3 bedroom , 3 bathroom family...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Villa Orzale-Arezzo Just at the border between Tuscany and Umbria, Villa Orzale is a country style villa with private swimming pool for 12 people. The area offers various cultural events like the 'Palio dei Rioni' (horse race) and with just a short drive from Arezzo you can...
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    52043, Castroncello, Castiglion Fiorentino
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It provides a fabulous combination of a great location and charming Tuscan style. A recent renovation offering lots of space, light and amazing views of the countryside along with a fabulous pool. It will easily appeal to discerning families looking for a bright and airy home and perfect location...
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    52044, Castiglion Fiorentino, Province of Arezzo
    Condo/Apartment - 6 Bedrooms, 6 Bathrooms, Sleeps 13
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Parking
    • Washer
    • Terrace
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    • Private Outdoor Pool (Unheated)
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Rustica has been fully restored and is now a beautiful holiday home. The furnishings are in keeping with Tuscan tradition including some antique pieces and the modern comforts of satellite televisions, and internet access have also been added. The ground floor of the villa has a large living...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Vacation Rentals at Nightingale's Villa, Tuscany1 / 74
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Washer
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    • Central Heating
    • Private Outdoor Pool (Unheated)
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    • Balcony
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just a short distance from the medieval town of Castiglion Fiorentino is 'Casa Usignoli'. This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms. The villa sits in one of the most sought after locations in...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 11
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    About this property
    Casa Sophia is a beautiful four bedroom family villa with fabulous Infinity Pool, lovely views and easy access The sweeping vista across the valley to Cortona and Castiglion Fiorention with the wonderful castle of Montecchio makes the perfect base for a friends and family home in Tuscany. Recently...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    10 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Air Conditioning
    • Sauna
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful villa, which has been recently and lovingly restored, is set amongst the pine woods and has sweeping views over the Chiana valley to Cortona and Lago Trasimeno. The villa has wi-fi internet, solar panels and the bedrooms are air-conditioned. Other Info The ground floor of the villa...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 10 Bedrooms, 1 Bathroom, Sleeps 10
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    Luxury Tuscan Villa, Villa Francesca,   Cortona Tuscany1 / 39
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed August 3, 2017
    This villa is ideally located for sightseeing and provides a great base if you want to explore Tuscany. The villa has clearly been recently renovated to a very high standard and...
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    About this property
    A lovely Tuscan home close to Cortona with exceptional views. A place to discover both Tuscany and Umbria. Villa Francesca is a luxury villa, perfect for both a relaxing and lazy holiday or to explore the many cultural delights of this region. From here you can easily discover Cortona , Pienza...
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    Location Information
    52044, Castiglion Fiorentino, Province of Arezzo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Parking
    • Balcony
    • Wi-Fi
    • Washer
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Vallibona is situated in the midst of peace and greenery in the gentle hills between Castiglion Fiorentino and Cortona, among olive groves and fruit trees, in a splendid panoramic position. The extensive property includes the main villa and the pool. Villa Vallibona has been restored with...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Four Bedroom Detached Villa Castiglion Fiorentino Villathis property is a gorgeous stone country house in a panoramic position with lovely views over the valley with the Tuscan town of Castiglion Fiorentino visible beyond. Surrounded by hills dotted with silvery olive groves,...
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    Location Information
    52043, Pieve di Chio, Castiglion Fiorentino
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Internet Access
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Martini has been carefully restored retaining all of its' original characteristics such as beamed ceilings and terracotta floors which are complemented by the traditional country furnishings creating a wonderful rustic and homely atmosphere with the addition of welcome modern comforts. The...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    7 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Owner's description: Walking distance to Castiglion Fiorentino. Villathis property is a beautiful holiday villa with attractive architectural features situated just outside Castiglion Fiorentino, a typical Tuscan town on the hills of the Valdichiana, surrounded by age-old olive groves and ancient...
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    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 15
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    Villa Panichi near historic center private pool Castiglion Fiorentino1 / 59
    (4)Excellent
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Balcony
    • Wi-Fi
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2017
    It is always with trepidation that one books something on the internet, but dealing with Luca, who is helpful and friendly and very informative, made it very easy. Our...
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    About this property
    In the shade of a cypress grove, between the warm colors of ancient stone and the restful green of the olive trees, you will discover an ideal place to spend your holidays in absolute tranquility in Tuscany! Villa Panichi is an old stone villa surrounded by olive trees on the slopes of the hill of...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 7 Bedrooms, 9 Bathrooms, Sleeps 18
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    Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool -  set within a  small Tuscan borgo1 / 33
    (7)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 1, 2017
    What a beautiful setting to relax in. This sympathetically restored farmhouse has three large bedroom modern kitchen and a terrace for outside eating that is in the sun for most...
    Reviewed September 25, 2017
    This charming house, with great views of the valley, was a great place to spend a relaxing week. Lovely pool and sun terrace. All mod- cons in the house. We were able to visit a...
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    About this property
    An attractive air conditioned stone farmhouse . The house offers high quality accommodation with outstanding views of the Val di Chio and Castiglion Fiorentino from the bedrooms, private pool and terraces. Casa dei Sogni is a newly renovated villa tracing its history back to the early 18th century....
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Villa Sant Antonio1 / 13
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Balcony
    • Parking
    • Wi-Fi
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 12, 2017
    We have spent one week holiday in Villa Sant Antonio. The place is absolutely stunning. The villa is very comfortable and beautifully furnished with great attention to the...
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    About this property
    Villa Sant Antonio is a beautiful holiday property in the heart of Tuscany, in Castiglion Fiorentino, close to Cortona and Arezzo. Great location in the middle of the olive growth, recently restored and beautifully furnished, full of art and antiques, with private swimming pool, makes it a great...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Terrace
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Guardian has been restored with great care and attention, leaving all of the original characteristics intact. The furnishings have been carefully chosen to reflect the true Tuscan style of the house and modern comforts have been added. The villa is on two floors and actually forms two...
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    Location Information
    52043, Castiglion Fiorentino, Province of Arezzo
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Castiglion Fiorentino Flight and Weather Info
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    • Local time: 08:29 PM (CET)
    • Exchange rate: 1 Euros = 1.15 U.S. Dollars
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