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$150

2 BR / 2 BA / Sleeps 4

Stefi G - Castiglion Fiorentino vacation rentals
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Stefi G

Castiglion Fiorentino house
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 - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$346

5 BR / 5 BA / Sleeps 11

Villa I Cipressi - Castiglion Fiorentino vacation rentals
1 / 26

$346

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Villa I Cipressi

Castiglion Fiorentino villa
5 BR / 5 BA / Sleeps 11 | Quick view

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These charming villa and cottage are nestled in the heart of the beautiful Val di Chiana, a few minutes' drive from the picturesque hilltop town of Castiglion Fiorentino and 15 minutes from Cortona. Here you can enjoy the peace and quiet of the Tuscan countryside and all the benefits of a lively historical town not …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$580

9 BR / 12 BA / Sleeps 18

Villa Mimi - Castiglion Fiorentino vacation rentals
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$580

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Villa Mimi

Castiglion Fiorentino house
9 BR / 12 BA / Sleeps 18 | Quick view

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In the quiet heartland the Valdichiana, at the top of a hill, stands Villa Mimi. Its high position gives this wonderful holiday home fantastic views across the Italian countryside. This property is an old country villa, carefully restored and now an exclusive private retreat that still enjoys its charming original …
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Satellite or cable TV
  • DVD Player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$55

1 BR / 1 BA / Sleeps 3

Big & Bright Studio in Tuscany near Cortona - WiFi - Castiglion Fiorentino vacation rentals
1 / 11

$55

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Big & Bright Studio in Tuscany near Cortona - WiFi

Castiglion Fiorentino condo
1 BR / 1 BA / Sleeps 3 | Quick view

Details

Big and bright studio apartment in Montecchio Vesponi, Castiglion Fiorentino provence of Arezzo in the midst of the Tuscan Hills consisting of double bedroom with ensuite bathroom including toilet, basin and large spacious shower, eating area with table and chairs, bar fridge, coffee and tea making facilities. This …
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Central heating
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

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$83

1 BR / 2 BA / Sleeps 2

B&B Podere le Spighe - Castiglion Fiorentino vacation rentals
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$83

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B&B Podere le Spighe

Castiglion Fiorentino B&B
1 BR / 2 BA / Sleeps 2 | Quick view

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Set in its spacious garden and surrounded by the countryside, B&B; Podere le Spighe (open 2014) is located in Castiglion Fiorentino. It offers an outdoor swimming pool, air-conditioned rooms, and a buffet-style breakfast provided daily. The large rooms have a rustic décor and wooden furnishings. Each comes with a …
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Porch
  • Suitable for the elderly

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$158

2 BR / 2 BA / Sleeps 4

Giaggiolo C - Castiglion Fiorentino vacation rentals
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$158

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Giaggiolo C

Castiglion Fiorentino house
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 leads…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$236

2 BR / 3 BA / Sleeps 4

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$236

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Giaggiolo F

Castiglion Fiorentino house
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 - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$213

3 BR / 3 BA / Sleeps 6

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$213

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Giaggiolo R1

Castiglion Fiorentino house
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 - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$134

2 BR / 2 BA / Sleeps 4

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$134

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Stefi 1

Castiglion Fiorentino house
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 - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$331

4 BR / 5 BA / Sleeps 8

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$331

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Villa Martini

Castiglion Fiorentino house
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, …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$394

9 BR / 9 BA / Sleeps 18

1 / 17

$394

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Villa Rustica

Castiglion Fiorentino house
9 BR / 9 BA / Sleeps 18 | Quick view

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9 Bedroom Detached Villa Arezzo Villa Rustica 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 space for dining al fresco and relaxing in the…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$213

3 BR / 3 BA / Sleeps 6

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Giaggiolo R2

Castiglion Fiorentino house
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 - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$149

2 BR / 2 BA / Sleeps 6

1 Reviews

$149

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Villa Manciano Vacation Rental at Il Fienile

Castiglion Fiorentino condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 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 restoring …
  • 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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$275

5 BR / 10 BA / Sleeps 10

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$275

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Tuscany Villa Principe

Castiglion Fiorentino villa
5 BR / 10 BA / Sleeps 10 | Quick view

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San Martino is ancient farm of 13th century of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio and Val di Chiana nearby the Hisorical Towns of Castiglion Fiorentino ( 10 min ), Cortona ( 25 min ), Arezzo ( 30 min ), Montepulciano ( 45 min ), FLORENCE , SIENA , PERUGIA at only …
  • Mountain Views
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Parking

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$219

5 BR / 2 BA / Sleeps 11

2 Reviews

$219

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Vacation Rentals at Nightingale's Villa, Tuscany

Castiglion Fiorentino villa
5 BR / 2 BA / Sleeps 11 | Quick view
Excellent2 Reviews

Details

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

Details

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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$157

3 BR / 2 BA / Sleeps 6

1 / 22

$157

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Villa Fiorentina-ideal for family with children

Castiglion Fiorentino house
3 BR / 2 BA / Sleeps 6 | Quick view

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Villa Fiorentina is the ideal place for a relaxing break immersed in nature. The Villa is surrounded by an olive grove of over two acres and enjoys stunning views of the nearby medieval town of Castiglion Fiorentino. It was recently renovated by the owners who have personally followed the work to create a modern and …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Outdoor Dining Area
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

Castiglion Fiorentino villa
2 BR / 1 BA / Sleeps 3 | Quick view
Excellent1 Reviews

Details

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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$209

3 BR / 3 BA / Sleeps 6

32 Reviews

$209

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Stylsh and Enchanting Home. Perfect Tuscan Retreat

Castiglion Fiorentino house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent32 Reviews

Details

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

Details

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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$118

2 BR / 1 BA / Sleeps 4

1 Reviews

$118

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Stefi 2

Castiglion Fiorentino house
2 BR / 1 BA / Sleeps 4 | Quick view
Very Good1 Reviews

Details

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 - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - 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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$325

2 BR / 2 BA / Sleeps 4

3 Reviews

$325

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Villa Margarita, Garden Apartment with lovely Pool

Castiglion Fiorentino villa
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent3 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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$69

1 BR / 1 BA / Sleeps 3

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$69

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Villa Sandia D

Castiglion Fiorentino house
1 BR / 1 BA / Sleeps 3 | Quick view

Details

Villa Sandia D is a welcoming apartment. It sleeps three people. From Villa Sandia D you will have a pleasant view of the garden. Villa Sandia D is 30 square meters (320 square feet). It features a shared swimming pool, a private patio, a shared garden, winter heating and WI-FI Internet access. You will be …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Deck
  • Parking
  • Garden
  • Smoking allowed - ask
  • Suitable for the elderly - ask

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$204

5 BR / 2 BA / Sleeps 9

1 / 15

$204

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Tuscany Villa Rigutini, Charming , Historic Home

Castiglion Fiorentino villa
5 BR / 2 BA / Sleeps 9 | Quick view

Details

Villa Rigutini is a lovely historic Tuscan villa dating back to 1400. It offers charm along with lots of space and a perfect home for either families or friends. Villa Rigatoni is a 7-room villa of 3230 square feet (300 m2) over 2 floors. Villa Rigatoni, dates back to the15th century. The villa is situated in a …
  • Mountain Views
  • Wireless Internet
  • Washing Machine
  • Outdoor Dining Area
  • Central heating
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$292

5 BR / 5 BA / Sleeps 10

3 Reviews

$292

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Villa Daniella, Charming & Elegant for 4-10 guests

Castiglion Fiorentino house
5 BR / 5 BA / Sleeps 10 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Set in the grounds of Tenuta San Martino sits this lovely stone villa with private pool, gardens and private access road. The villa enjoys amazing views of the historic Valley of Chio and the medieval town of Castiglion Fiorentino. Nestled amongst ancient olive groves, and surrounded by the bucolic splendor of …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

exceptional place: Peaceful and our Perfect home form Home

Left on Feb 11, 2013 for a stay in August 2012

We did enjoy our two weeks here. It was home from home. Relaxed and care free.

The property was clean and bright, everything for our needs. Of course, we do not have a pool at home - and this is what makes a holiday - having a special something for us all to enjoy. The views are marvelous and the surrounding just perfect.

The journey down the hill finds the the closest shop and restaurant. a …

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$149

2 BR / 2 BA / Sleeps 5

4 Reviews

$149

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Lovely Tuscan Cottage set in Private Estate of Tuscany

Castiglion Fiorentino cottage
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

"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

(4)

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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$215

2 BR / 1 BA / Sleeps 4

19 Reviews

$215

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Tuscany, Casa Serena. Private Pool - for 4 guests

Castiglion Fiorentino villa
2 BR / 1 BA / Sleeps 4 | Quick view
Excellent19 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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