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Book Online or call HomeAway Booking Assistance 888-829-7076
Book Online or call HomeAway Booking Assistance 888-829-7076

Tranquil Tuscan Retreat, Perfect for families of all ages looking to enjoy a Tuscan vacation

Bedrooms 5
Space 0 sq. ft.
Property type villa
Minimum Stay 0 - 7 nights


About the property

APRIL and MAY SPECIALS ,3 bedrooms, 3 bathrooms, Infinity Edge private Pool,

The view from here is - "just stunning" And for 2017, special deals.

Villa Castello Roccolo is for sure, a really special property tucked away on the sleepy hillside of Castiglion Fiorentino and where guests can make this their "home from home" -

The property welcomed its first guests in May 2016, - The villa is set within an olive grove with amazing views towards the Tuscan hill town of Castiglion Fiorentino . Adjacent to the larger villa is a (deconsecrated) church from the 12th century which now restored and can be used for smaller wedding and anniversary celebrations

THe villa is perfect for a fmaily vacation orfor freinds whanting a place to call home in TUscany. THe many features make it a delight and a place to really enjoy a week or two away. The Villa and its annex provide three bedrooms, three bathrooms, modern kitchens, 2 sitting rooms, a vast terrace with some of the loveliest views of the valley and the town of Castiglion along with the private Infinity Edge pool - strategically situated to enjoy the fabulous views.

It is about 3 km from the town, where there are many restaurants, bars and shops and, there is also small shop,bar and restaurant just across the valley if you did not want to travel into the town,

Much like the other villas here, this is also a good location - an excellent base to explore Tuscany its many hill towns, festivals, wineries and countryside including easy easy day trips to Cortona, Pienza, Montepulciano, Siena etc - Florence is also easy by either car (1 hour) or by train from our local station.

This is one of our first reviews from May 2016.

“The houses are surrounded by a beautiful old olive grove. There are two terraces overlooking the valley and a very nice infinity swimming pool. The view is breathtaking. I have been in this valley before but the view here beats everything. There is a small terrace in the back to catch the early morning sun. The large terraces in the front catch the sun from 10 am to sunset. For people like me who love to read in the shade : plenty of shade available under the surrounding trees. The olive groves around the houses are actually grassy meadows, ideal for children's play. In the woods on top of the hill behind the house lie the remains of a 13 th century castle. You have to drive up a steep access road from the valley floor to reach this house. The next and only other house is 100 m down. The road continues up the hill for another 2 km, winding through beautiful olive groves and forests, offering breathtaking views. Then the road changes into a hiking trail that joins the hiking trail that circumvent the valley. We were the first occupants in a newly developed property. We were two couples and stayed a week in May 2016. The property consist of two houses. The smaller one has one bedroom, with a king size bed, bathroom and a living space with kitchen. Tho other house has two bedrooms, one with king size bed and the other with two single beds. The house has two bathrooms. A dining room, sitting room and separate kitchen. It Being a new property I was amazed by the attention to detail that went into the fittings and decoration. To name a few which very often lack in other properties: - there are no street lights around, the garden and swimming pool has plenty of discrete lights to make walking in the dark safe - lots of power points all over the house to charge electronics - very well outfitted kitchens with very good stoves, large fridges, the kitchen in the larger house has a dishwasher - plenty of dishes, pans, bowls and other kitchen utensils to make holiday cooking practical ”

Hendrik, NL.

in the area are tennis courts, horse riding and , now the new Golf Course at Cortona - currently with 9 holes, and soon to have a full 18 holes - designed by Gary Player....

More Details


Cortona Villa Accommodation and Amenities

Property Type:
  • villa
Floor Area:
  • 0 sq. ft.
  • 2 stories
  • 3 Bathrooms
  • bathroom - toilet , shower , bidet
    bath 2 - toilet , shower , bidet
    bath 3 - toilet , shower , bidet
  • 3 bathrooms, with bidet, WC and powerful "RAIN" showers
  • 5 Bedrooms, Sleeps 6
  • three bedrooms, one with private balcony terrace,
Private Infinity pool, private gardens and olive grove - THe best view in the valley........ The property can also be used for weddings and ceremonies . THe private chapel (deconsecrated) can be made acvauable. Although the accomodation is for 6 guests, there is a large function room and the terrace which is about 9 meters by 5 , plus the grounds makes a great place for clebrations


Wonderful! 4.8/5 -
(10 traveler reviews)

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Tranquil Tuscan Retreat, Perfect for families of all ages looking to enjoy a Tuscan vacation
average rating of 4.8 based on 10 reviews
United Kingdom

“Home” for the Holidays

  • 5 of 5

we were looking for a place which we could relax and, use it as “our home” inviting family and friends over the Holiday season. The layout here ( 1 large and 1 small stone house) ideal for us, The larger for us all to gather and enjoy and the smaller house providing an independent private place.

The villa and its little chapel are the result of a long restoration, and it’s easy to see that detail was carefully followed. There remain a few things to do, but nothing to take away the enjoyment.

for the brighter sunny days, the views of the town and landscape always a joy. and the many walks around the place added to the pleasure of staying in a quiet part of tuscany .

  • Submitted: Jan 12, 2018
  • Stayed: December 2017
  • Source: Tuscan Charm Ltd.
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Dubai, United Arab Emirates

Great place for our extended family

  • 5 of 5

The arrangement of a main villa and annex was perfect for us - giving us the feel of a family home with the additional "privacy" for our parents to use the close by annex. Enthusiastic welcome and very helpful guidance to localities including the markets of Camucia Cortona and some good restaurants all added to our enjoyment and enhanced our vacation here.

The villa's views are certainly more than exceptional and, like the villa , the photos do not amply show the beauty of the the villa, its pool and its surrounds. 10/10

  • Submitted: Sep 10, 2017
  • Stayed: September 2017
  • Source: Tuscan Charm Ltd.
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Belfort, , , France

From the house the view out on the valley is truly amazing,

  • 3 of 5

We had a wonderful stay with our family at Villa Castello Roccolo. When we arrived, we had a lovely welcome by Terry who made us feel at ease throughout our stay and gave us helpful tips to find our way around Castiglion Fiorentino. The house itself is cozy and lovely, with a rich history and wonderfully renovated by the owner. The amenities in the house were sufficient to enjoy wonderful home-cooked meals which we could eat outside in the shade of the trees. From the house the view out on the valley is truly amazing, including the olive trees, the nearby town on a hill top, beautiful sunsets and lit-up skies filled with stars… stunning really. The town of Castiglion Fiorentino is actually pretty close and offers a very nice selection of restaurants and it is much less touristy than the surrounding towns. There is castle nearby that is currently under renovation and definitely worth a visit. In short, we can definitely recommend a stay at Villa Castello Roccolo because of the house itself, its atmosphere and amenities, and the amazing Tuscan surroundings.

  • Submitted: Aug 8, 2017
  • Stayed: August 2017
  • Source: Tuscan Charm Ltd.
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United Kingdom

Three friends enjoying Tuscany for the first time

  • 5 of 5

Choosing a place that would give us private personal space as well as communal ares to enjoy our times together was important and, so finding this place was great. The two buildings (one an annex with bedroom, bathroom and a small sitting area, the main villa with two bedrooms 2 bathrooms) along with the incredibly large terrace and, of course the pool and their views provided me with inspiration for some painting and for each of us enjoyable lunches and dinners to enjoy each others company and the pleasures of the whole surrounds.

The tiny church which is being restored adjoining the property gives it a comforting hamlet feel to the property and the woodland and castle ruins a lovely place to wonder in the shade the early mornings etc.

Visiting towns around here are all lovely - but sometimes disappointing when churches and museums are closed - (especially between 13-16) - so a little planning is suggested. There is an informative guide book of many things to do which helped us, and along with the greeting and warm welcome made us feel instantly special -

  • Submitted: Aug 3, 2017
  • Stayed: July 2017
  • Source: Tuscan Charm Ltd.
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Vlaams Gewest, Belgium

Great Tuscan family stay

  • 5 of 5

Accurately presented and very enjoyable. The house clean, comfortable and all as we had hoped. The pool was a perfect place to spend lazy days , and for us to tour the many towns here was easy.

  • Submitted: Aug 3, 2017
  • Stayed: July 2017
  • Source: Tuscan Charm Ltd.
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Lent, Netherlands

Great location, beautiful house, stunning views and very private. Recommended!

  • 5 of 5

We very much enjoyed our stay at Villa Roccolo. We would definitely recommend this to others!


- beautiful view, can hardly get any better

- great location, very private

- beautiful pool, great surroundings

- close to nice towns and villages

- very special place, close to an old ruine (no danger) and a little chapel.

- nicely refurbished house, with respect to original features

- modern interior, nice showers etc

- many facilities (linen, pottery, dish washer, washing machine, coffee and tea)

- prompt reply of owner / landlord in case of any issues

- two separate locations (10m distance), ideal for two couples, a family with bigger kids or something alike.

Just some things that we would consider:

- the road towards the property is quite bumpy and unpaved. not much space to pass vehicles. Owners should maybe consider to ask municipality to improve this.

- the terrace really should get a roof, then it's a superb dining location.

- parking space at the property could be slightly improved (more space)

- airconditioning is absent, electricity is expensive indeed, but this would definitely add to the house. Particularly the small house gets quite hot in summer time.

- The property is not ideal for very young children, but the owners very friendly arranged cots, high chairs en some fences. If a fenced playing field would be there, it would be absolutely perfect for young kids as well.

- The location is quite expensive, particularly in the high season.

In short, we had a superb stay at Villa Roccolo, and we are sure anyone will enjoy this great holiday location!

  • Submitted: Jul 2, 2017
  • Stayed: June 2017
  • Source: Tuscan Charm Ltd.
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Property Manager

Speaks: english, italian
Manager indicates their response time is:
Within 12 hours
Calendar last updated:
February 17, 2018


Nearest Airport
95 Minutes
Nearest Restaurant
10 Minutes


Rates & Availability

Taxes and fees are additional


  • Heating charges are by consumption .

    Cleaning fee for the house is payable at house

    Security deposit of payable at house

  • Contractual booking deposit: 20.00% rent