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$239

4 BR / 6 BA / Sleeps 8

3 Reviews

$239

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Vallibona, rare panoaramic Villa in the midst of peace and greenery.

4 BR / 6 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

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 great care using …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

A memorable stay in Villa Vallibona

Left on Sep 23, 2011 for a stay in July 2011

We have enjoyed every single day of our one-week family holiday in Villa Vallibona.
The villa has a lot of charm and a splendid view on the neighbouring countryside. Very calm, nicely equipped and very comfortable. Castiglion Fiorentino has also proved to be an excellent spot for one-day trips in Tuscany and Umbria. Andrea (the villa's owner) has been a very attentional host.
Highly recommended!

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$213

3 BR / 3 BA / Sleeps 6

32 Reviews

$213

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Stylsh and Enchanting Home. Perfect Tuscan Retreat

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 32 Reviews

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Reviews

(32)

Guest Comment: "I have never slept so well with the pristine mountain air wafting through the open windows at night. If you want to have a "non-touristy" true get away this is the house for you" If you are planning a visit to Cortona, Castiglion Fiorentino and beyond, Villa Coppa is really a lovely and stylish home …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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Reviews

(32)

Charming!!!

Left on Oct 15, 2011 for a stay in October 2010

It is exactly what you would want if you
were visting Tuscany-It is cozy and comfortable-The decor is delicious and oozes charm- mixed with sophistication...
I can't wait to go back!!!

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$392

6 BR / 6 BA / Sleeps 15

Villa Galileo - Castiglion Fiorentino vacation rentals
1 / 13

$392

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Villa Galileo

6 BR / 6 BA / Sleeps 15 | Quick view

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Villa Galileo (13 +2 pers.) Surrounded by olive groves and woods among the Tuscan hills villa Galileo is the perfect place for a peaceful and relaxing stay. It belongs to a farm situated between the city of Arezzo and the Etruscan town of Cortona and just minutes away from the medieval village of Castiglion …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Parking
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$223

5 BR / 2 BA / Sleeps 11

2 Reviews

$223

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"Casa Usignoli" - Nightingale's Villa, Tuscany

5 BR / 2 BA / Sleeps 11 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

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 Tuscany. The villa …
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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Reviews

(2)

this could be heaven!

Left on Jan 17, 2014 for a stay in June 2013

A well maintained, bright and inviting home for our two weeks in Tuscany.

Beautiful views and amazing sunsets, a crystal blue pool and deep blue sky. In the evening, fireflies to entertain us as we sipped local wine and planned the next days tour.

Rooms the largest we found on our recent tours of Italy, and very helpful agent too. This could be heaven! Fantastic value, fantastc place, …

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$139

2 BR / 1 BA / Sleeps 3

1 Reviews

$139

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3 Cottages in an ancient Tuscan village with Pool

2 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

"Simple and Lovely" Borgo Tranquilita is a charming peaceful and quiet "village" of three cottages set amongst some of the most spectacular scenery that makes Tuscany one of the stunning places to visit. It is surrounded by typical Tuscan woodland with some breathtaking views. The cottages are available individually …
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Family Vacation Toscana - we enjoyed the place and company

Left on Aug 18, 2012 for a stay in July 2012

A much needed sunshine vacation for the family. Our two weeks here were very enjoyable and we and the children made new friends.

the cottage is charming, and as we expected, comfortable bed and nice rooms. Outside the terraces was very relaxing for our meals and the barbecue gave us the opportunity to try the famous fiorentino beefsteak.

The pool was fun for the children and relaxing for us …

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$336

4 BR / 3 BA / Sleeps 11

The Dreamful Holiday House ! - Castiglion Fiorentino vacation rentals
1 / 42

$336

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The Dreamful Holiday House !

4 BR / 3 BA / Sleeps 11 | Quick view

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VILLA IN TUSCANY WITH PRIVATE POOL AND IN A VERY PANORAMIC POSITION. Rural holiday house is placed on the silver hills covered with olives groves between the villages of Castiglion Fiorentino and Cortona (endowed with all kind of shops and services). It set in a very panoramic position and a stone's throw away from …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$112

2 BR / 2 BA / Sleeps 4

1 / 10

$112

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Giaggiolo C

2 BR / 2 BA / Sleeps 4 | Quick view

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Two Bedroom Split Level Detached Cottage Castiglion Fiorentino Giaggiolo C is a charming detached cottage on a fully restored Tuscan hamlet situated in a gorgeous position on a hilltop. The cottage opens onto its’ own terrace and garden perfect for relaxing and dining al fresco. A pathway through the grounds …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$152

2 BR / 3 BA / Sleeps 4

1 / 9

$152

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Giaggiolo F

2 BR / 3 BA / Sleeps 4 | Quick view

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Two Bedroom Split Level Detached Cottage Castiglion Fiorentino Giaggiolo F is a lovely detached cottage on a fully restored Tuscan hamlet situated in a gorgeous position on a hilltop. The cottage opens onto its own large terrace shaded by a pergola and is surrounded by a pretty garden. A pathway through the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$216

3 BR / 3 BA / Sleeps 6

1 / 9

$216

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Giaggiolo R1

3 BR / 3 BA / Sleeps 6 | Quick view

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Three Bedroom Ground Floor Apartment Castiglion Fiorentino Giaggiolo R1 is a spacious apartment on the ground floor of the manor house on a fully restored Tuscan hamlet situated in a gorgeous position on a hilltop. The apartment opens onto its’ own terrace and garden perfect for relaxing and dining al fresco. A …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$104

2 BR / 2 BA / Sleeps 4

1 / 8

$104

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Stefi G

2 BR / 2 BA / Sleeps 4 | Quick view

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Two Bedroom Split level Detached Cottage Castiglion Fiorentino Stefi G is a characteristic detached cottage on a pretty little estate, once a farming homestead, situated in a lovely position on a hill overlooking the valley beyond. The cottage apartment opens onto its own terrace and garden area in the well kept…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$88

2 BR / 1 BA / Sleeps 4

1 Reviews

$88

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Stefi 2

2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Two Bedroom First Floor Apartment Castiglion Fiorentino Stefi 2 is a characteristic apartment on a pretty little estate, once a farming homestead, situated in a lovely position on a hill overlooking the valley beyond. The apartment has its own terrace and garden area in the well kept grounds below, perfect for …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Schön ruhig gelegen, mit herrlichem Panoramablick auf C.Fiorentino

Left on Sep 13, 2013 for a stay in September 2013

Auf einem zweiwöchigen Ferientrip in die Toskana über Südtitol mit dem eigenen Auto ohne vorherige Buchung hatten wir dieses wunderbare Appartement in die Auswahl miteinbezogen. Da wir noch nie in der Toskana waren entschlossen wir uns eine Autostunde vor Florenz hier einmal anzurufen. Die Eigentümerin war sehr nett und sendete uns per SMS

die genauen Standortdaten. Aus der einen Woche sind…

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$136

3 BR / 3 BA / Sleeps 6

1 / 9

$136

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Giaggiolo R2

3 BR / 3 BA / Sleeps 6 | Quick view

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Three Bedroom First Floor Apartment Castiglion Fiorentino Giaggiolo R2 is a spacious apartment on the first of the manor house on a fully restored Tuscan hamlet situated in a gorgeous position on a hilltop. As the house is built of a slope, the apartments entrance is accessed via its’ own terrace and garden …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$240

4 BR / 5 BA / Sleeps 8

1 / 19

$240

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Villa Martini

4 BR / 5 BA / Sleeps 8 | Quick view

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Four Bedroom Detached Villa Castiglion Fiorentino Villa Martini is a lovely example of a Tuscan farmhouse and annex, situated in a wonderful elevated position with amazing views of the countryside all around. The villa and it’s dependance are enclosed in their own well kept grounds where, just a few steps away, …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$192

4 BR / 4 BA / Sleeps 8

1 / 14

$192

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Villa Guardian

4 BR / 4 BA / Sleeps 8 | Quick view

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Four Bedroom Detached Villa Castiglion Fiorentino Villa Guardian 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, the villa is immersed in its’ own …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$96

2 BR / 2 BA / Sleeps 4

1 / 8

$96

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Stefi 1

2 BR / 2 BA / Sleeps 4 | Quick view

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Two Bedroom Ground Floor Apartment Castiglion Fiorentino Stefi 1 is a characteristic apartment on a pretty little estate, once a farming homestead, situated in a lovely position on a hill overlooking the valley beyond. The apartment opens onto its own terrace and garden area in the well kept grounds, perfect for …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$430

4 BR / 3 BA / Sleeps 8

1 / 29

$430

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Castiglion Fiorentino - 44198001

4 BR / 3 BA / Sleeps 8 | Quick view

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This beautiful stone villa in medieval style is situated in a splendid location, romantically strategic. It overlooks the valleys of the Valle di Chiana and the Val di Chio offering a panorama of the landscape below immersed in olive groves, rich in beauty and history. This is the ideal place for those who would …
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

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$219

6 BR / 5 BA / Sleeps 13

1 / 34

$219

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Castiglion Fiorentino - 57464001

6 BR / 5 BA / Sleeps 13 | Quick view

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Ancient farmhouse with private pool situated south of Tuscany. This villas has been tastefully restored with its original charm and architectural features preserved and it has been turned into a welcoming country house. The interiors offer a nice combination of rustic and ancient pieces. This property enjoys beautiful…
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

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$154

2 BR / 2 BA / Sleeps 5

1 / 32

$154

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Castiglion Fiorentino - 61097006

2 BR / 2 BA / Sleeps 5 | Quick view

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Off the main tourist tracks, situated in the south-eastern part of Tuscany and close to Lake Trasimeno, Polvano was built three hundred years ago and is still owned by the Polvani family, who restored the estate recently. Great care was applied to maintain the estate’s architectural characteristics and …
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

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$114

2 BR / 1 BA / Sleeps 4

1 / 28

$114

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Castiglion Fiorentino - 61097004

2 BR / 1 BA / Sleeps 4 | Quick view

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Off the main tourist tracks, situated in the south-eastern part of Tuscany and close to Lake Trasimeno, Polvano was built three hundred years ago and is still owned by the Polvani family, who restored the estate recently. Great care was applied to maintain the estate’s architectural characteristics and …
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

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$154

1 BR / 1 BA / Sleeps 3

1 / 30

$154

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Castiglion Fiorentino - 61097002

1 BR / 1 BA / Sleeps 3 | Quick view

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Off the main tourist tracks, situated in the south-eastern part of Tuscany and close to Lake Trasimeno, Polvano was built three hundred years ago and is still owned by the Polvani family, who restored the estate recently. Great care was applied to maintain the estate’s architectural characteristics and …
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

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$114

2 BR / 1 BA / Sleeps 4

1 / 28

$114

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Castiglion Fiorentino - 61097003

2 BR / 1 BA / Sleeps 4 | Quick view

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Off the main tourist tracks, situated in the south-eastern part of Tuscany and close to Lake Trasimeno, Polvano was built three hundred years ago and is still owned by the Polvani family, who restored the estate recently. Great care was applied to maintain the estate’s architectural characteristics and …
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

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$146

2 BR / 1 BA / Sleeps 4

1 / 31

$146

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Castiglion Fiorentino - 61097001

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Off the main tourist tracks, situated in the south-eastern part of Tuscany and close to Lake Trasimeno, Polvano was built three hundred years ago and is still owned by the Polvani family, who restored the estate recently. Great care was applied to maintain the estate’s architectural characteristics and …
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$122

1 BR / 1 BA / Sleeps 2

1 / 28

$122

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Castiglion Fiorentino - 61097005

1 BR / 1 BA / Sleeps 2 | Quick view

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Off the main tourist tracks, situated in the south-eastern part of Tuscany and close to Lake Trasimeno, Polvano was built three hundred years ago and is still owned by the Polvani family, who restored the estate recently. Great care was applied to maintain the estate’s architectural characteristics and …
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask

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$151

2 BR / 2 BA / Sleeps 6

1 Reviews

$151

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Villa Manciano - Il Fienile

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Villa Manciano is a very typical old stone Holiday House that was supposed to be also an elementary school about 100 years ago, for the kids of the rural Manciano area. The property is more than 3 acres (12.000 sq. meters) located in the strategical area of the Chiana Valley, in the Cortona area. The fine …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Amazing!

Left on May 05, 2013 for a stay in May 2011

It's already 2 years since our lovely holiday in Tuscany and Villa Manciano, but since we just found Villa Manciano here on tripadvisor we feel that we have to write a few words. The Villa is absolutely stunning. We were 2 couples travelling and stayed in Il Fienile apartment. The apartment is big, with 2 beautiful bedrooms and bathrooms, a big fully equipped kitchen and a big living room with tv…

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$114

2 BR / 2 BA / Sleeps 4

1 / 20

$114

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Casa Pantoufle Castiglion Fiorentino (Arezzo)

2 BR / 2 BA / Sleeps 4 | Quick view

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Casa Pantoufle is an old, stone farmhouse surrounded by silver olive trees in a panoramic, hill position at about 800 m above sea level and overlooking the Castle of Montecchio and the whole Valdichiana Valley. The house is reached via a scenic route of which the last 500 m. unpaved, and is only 5 km away from the …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$134

1 BR / 1 BA / Sleeps 4

1 / 15

$134

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Dreamful rooms or apartments in the heart of Tuscany

1 BR / 1 BA / Sleeps 4 | Quick view

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The Tanganelli family are delighted to welcome you to their tastefully restored 13th century convent Le Santucce. We have lovingly converted this historic building to offer 19 superb rooms/apartments. We offer: - Bedrooms with en-suite bathroom - Single rooms - Double rooms - Triple rooms - 4 persons room - …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Balcony or terrace
  • Parking
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$330

2 BR / 2 BA / Sleeps 4

3 Reviews

$330

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Villa Margarita, Garden Apartment with lovely Pool

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Castello Margarita's Garden apartment is the ideal spot for those seeking relaxation and the convenience to explore Tuscany. Ideal for 2- 5 guests, It provides a compelling combination of a great location and charming farmhouse style. The property is offered as either two apartments (one for 4 guests and the …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(3)

Beautiful property with stunning views

Left on May 24, 2013 for a stay in August 2012

We stayed in the lower apartment of the property for two weeks. The property is very, very beautiful and spacious and the views are absolutely stunning. Very well maintained. One of our sons is in a wheelchair or uses a walking device. We had to help him to get to the pool and back, but on both places he could get around all by himself. The owner did make our stay very comfortable. They even …

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$263

4 BR / 3 BA / Sleeps 8

2 Reviews

$263

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Villa Senaia- Tuscany

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Villa Senaia - Enjoy your stay In stunning Tuscany, along its endless artistic heritage and countryside, where stretches of silvery olive trees stare after vineyards and cypress trees, lies the Villa Senaia. An ancient stone farmhouse, located in a strategic position where it is easy to uncover many of the …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(2)

Add this to your bucket list!

Left on Feb 06, 2014 for a stay in September 2013

we (a group of 7 adults)have stayed at Villa Senaia twice so far (for 2 weeks at a time) and have planned our 3rd visit for Sept. 2014. There is so many positive about this wonderful place and part of Italy, it shouldn't be missed. The villa is spectacular with breathtaking views of the valley and the walled city of Castiglion Fiorentino. It sits on a hill a short distance from CF and has …

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$151

2 BR / 2 BA / Sleeps 5

3 Reviews

$151

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Lovely Tuscan Cottage set in Private Estate of Tuscany

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

"How lucky the locals are to live in a place as rich in natural beauty as here" Mary-Beth, June 213. Set in one of Tuscany's most pretty valleys you will find this absolutely charming estate and, this lovely cottage with its "gorgeous pool". Close to the famous towns of Cortona, Castiglion Fiorentino and Arezzo…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

The most relaxing and beautifull country holiday .

Left on Nov 17, 2011 for a stay in August 2007

Massimo was ever freindly and helpfull he has a lovely warm family ,ideal hosts .The home was simple and comfortable with stunning views and a large ,clean, pool.We found it a very central location as soon as we had our bearings going as far as Rome or Florence on a day trip no trouble but our favourite place was Cortona.Going in august we found it a little too warm on a couple of days but the …

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$214

2 BR / 1 BA / Sleeps 4

19 Reviews

$214

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Tuscany, Casa Serena. Private Pool - for 4 guests

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 19 Reviews

Details

Reviews

(19)

A really charming little cottage/ villa in a very private location with its own private pool. Set along a Tuscan hillside in the middle of olive grove, Casa Serena (Serenity) provides perfect peace and seclusion. From the garden and pool areas, there are spectacular views over the Val di Chio and, some of the most …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(19)

Relaxation in Tuscany's Countryside

Left on May 20, 2011 for a stay in May 2010

Certainly off the beaten track, this lovely chalet house was just what we needed. Relaxing, secluded with wonderful views across the valley and to the garden and olive trees.

"Charmingl” very comfortable bedrooms, and comfy family room where we relaxed and on the only rainy day, rediscovered chess and some board games left by the owners.

The pool is just there! We sat in the porch for …


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