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$238

4 BR / 6 BA / Sleeps 8

3 Reviews

$238

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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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$390

6 BR / 6 BA / Sleeps 15

Villa Galileo - Castiglion Fiorentino vacation rentals
1 / 13

$390

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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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$222

5 BR / 2 BA / Sleeps 11

2 Reviews

$222

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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

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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$910

9 BR / 9 BA / Sleeps 18

Villa Michele - Castiglion Fiorentino vacation rentals
1 / 18

$910

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Villa Michele

9 BR / 9 BA / Sleeps 18 | Quick view

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Villa Michele is situated in the centre of Valdichiana, close to Cortona andnbspand Arezzo, its location offers the possibility to reach quickly the important historic and artistic cities like Florence, Montepulciano, Siena, Assisi and Perugia. Villa Michele is an old country residence skillfully restored and …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Fireplace
  • Washing Machine
  • Smoking allowed
  • Wheelchair accessible

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$280

4 BR / 3 BA / Sleeps 8

Casale Fiorentina - Castiglion Fiorentino vacation rentals
1 / 9

$280

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Casale Fiorentina

4 BR / 3 BA / Sleeps 8 | Quick view

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This enchanting , newly renovated stone villa in situated in a wonderful, panoramic position overlooking the valley of the 'Val di Chiana'. The villa is surrounded by olive groves and fields of grapevines and is the perfect setting for a relaxing Tuscan vacation being in the perfect position to enjoy all of the sites…
  • Private Pool
  • Internet Access
  • Fireplace
  • Washing Machine
  • Balcony or terrace
  • Smoking allowed

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$908

9 BR / 9 BA / Sleeps 18

Villa Valdichiana Villa in Tuscany, Arezzo villa, holiday in Italian villa, - Castiglion Fiorentino vacation rentals
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$908

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Villa Valdichiana Villa in Tuscany, Arezzo villa, holiday in Italian villa,

9 BR / 9 BA / Sleeps 18 | Quick view

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(Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Villa Valdiciana 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, surrounds the property. …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$290

5 BR / 3 BA / Sleeps 9

1 / 16

$290

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Villa di Cozzano ~ RA34669

5 BR / 3 BA / Sleeps 9 | Quick view

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Please note these Check-in Day Requirements for this property: Aug 14 - Nov 29 : Friday, Saturday, Sunday, Monday, Tuesday, Wednesday and Thursday check-out required.; Oct 29 - Nov 29 : Thursday, Friday and Saturday check-out required.; 8-room villa 300 m2 on 2 levels, on the ground floor, renovated, antique and …
  • Shared outdoor pool (unheated)
  • Washing Machine
  • Balcony or terrace
  • Parking
  • Garden
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$382

6 BR / 5 BA / Sleeps 16

1 / 20

$382

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Santo Stefano

6 BR / 5 BA / Sleeps 16 | Quick view

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Ground floor The first apartment is located on the Ground Floor and is composed of a living room with a sofa bed, fireplace, well equipped kitchen, 1 master bedroom with a private bathroom with bathtub, 1 bedroom with 2 single beds, and a bathroom with a bathtub. The entrance to the apartment is through a private …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Garden
  • Dishwasher
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$334

4 BR / 3 BA / Sleeps 11

1 / 42

$334

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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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$206

5 BR / 2 BA / Sleeps 9

1 / 15

$206

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Tuscany Villa Rigutini, Charming , Historic Home

5 BR / 2 BA / Sleeps 9 | Quick view

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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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$302

7 BR / 9 BA / Sleeps 16

1 Reviews

$302

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Villa del Colle ideal location for family reunion

7 BR / 9 BA / Sleeps 16 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Villa del Colle is an antique Tuscan farmhouse recently reconstructed situated in a beautiful hilly position. The painstaking reconstruction of the farmhouse has kept the fascination of the antique Tuscan residence with Terracotta tiled floors, visible stones and visible wooden beams. The farmhouse is very spacious …
  • Mountain Views
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful stay with friends

Left on Oct 12, 2011 for a stay in August 2011

Nice site, great hospitality, wonderful holiday with our friends.
Great pool also for night swimming.

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$278

5 BR / 10 BA / Sleeps 10

1 / 40

$278

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Tuscany Villa Principe

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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$239

4 BR / 5 BA / Sleeps 8

1 / 19

$239

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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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$191

4 BR / 4 BA / Sleeps 8

1 / 14

$191

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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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$217

6 BR / 5 BA / Sleeps 13

1 / 34

$217

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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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$428

4 BR / 3 BA / Sleeps 8

1 / 29

$428

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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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$881

9 BR / 10 BA / Sleeps 18

1 Reviews

$881

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Villa Rental in Tuscany, Castiglion Fiorentino - Villa Principessa

9 BR / 10 BA / Sleeps 18 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

What made you realize how much you'd love a holiday in Tuscany? Was it the thought of the beautiful countryside scenery, the delicious cuisine, or all the charming hilltop towns you could explore? It may have been all of the above and if so, you'll absolutely find each of these while at this Italian villa. Just …
  • Sauna
  • Internet Access
  • Washing Machine
  • Central heating
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Tom's review of Villa Principessa

Left on Sep 03, 2011 for a stay in August 2011

Very nice. Beautiful property, good amenities.

The views.

Bees made it hard to open the windows and doors. Air conditioning is not up to U.S. standards.

Easy to drive to Montepulciano, Cortona, Montalcino.

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$350

5 BR / 5 BA / Sleeps 11

1 / 26

$350

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Villa I Cipressi

5 BR / 5 BA / Sleeps 11 | Quick view

Details

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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$262

4 BR / 3 BA / Sleeps 8

2 Reviews

$262

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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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$278

6 BR / 5 BA / Sleeps 12

1 / 50

$278

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Exceptional, Luxury Tuscan Vacation Home.

6 BR / 5 BA / Sleeps 12 | Quick view

Details

This exceptional, luxurious and impeccable private estate in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Extraordinary views of the famed Montechio Castle and, the Etruscan Tuscan hill town of Castiglion Fiorentino can be easily seen from the many terraces that surround the …
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

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$490

7 BR / 1 BA / Sleeps 14

1 / 18

$490

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Villa Il Castello ~ RA34665

7 BR / 1 BA / Sleeps 14 | Quick view

Details

Please note these Check-in Day Requirements for this property: Feb 04 - Jan 10 : Wednesday check-in required, Saturday and check-out required.; Feb 15 - Jan 10 : Saturday and check-out required.; Feb 22 - Jan 10 : Saturday and check-out required.; Mar 01 - Jan 10 : Saturday and check-out required.; Mar 08 - Jan 10…
  • Shared outdoor pool (unheated)
  • Fireplace
  • Washing Machine
  • Parking
  • Grill
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$295

5 BR / 5 BA / Sleeps 10

3 Reviews

$295

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Villa Daniella, Charming & Elegant for 4-10 guests

5 BR / 5 BA / Sleeps 10 | Quick view
“ Excellent ” 3 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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