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Villa Castello Roccolo

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  • Castiglion Fiorentino villa pool
  • Castiglion Fiorentino villa exterior
  • Castiglion Fiorentino villa interior
  • Castiglion Fiorentino villa bedroom

Villa Castello Roccolo

Castiglion Fiorentino villa for 6 with pool, Tuscany

A wonderful Tuscan home for family and friends to enjoy with beautiful views , a private infinity pool and, a tranquil position.

The villa adjoins the remains of the ancient fortress dating back to the 11th century. The renovation of the villa now provides a really lovely home to enjoy these tranquil surroundings. The main villa has two bright and cosy bedrooms and two bathrooms. On the ground floor there is a modern kitchen, separate sitting and dining room and access to the vast sun deck terraces and the infinity pool. Adjacent to the villa, (15 meters) is the independent studio on one level offering a large double bedroom, modern bathroom, sitting room and small kitchen area. The studio has three french doors with access to the olive groves, gardens, terraces and pool.

This is Villa Castello Roccolo and 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 villa is set amongst olive groves and typical Tuscan landscape. Adjacent to the main villa is a small church which is slowly being renovated to complete the original borgo.

The infinity pool and the very large terraces have, perhaps the very best views in this treasured valley. Throughout the year the fields below change their appearance, form sunflowers to fields of poppies - whatever the time of year, the views from here are just wonderful. The town of Castiglion Fiorentino is the backdrop of this perfect location.

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,

the villa is in a great 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.

The olive groves around the houses are ideal for children's play. In the woods on top of the hill behind the house lie the remains of a 11 th century fortress/castle.The drive up to the villa provides some excellent views - and then - you will arrive at the parking area below the main house where the "real views" are there to enjoy.

There is easy access into the studio with its facilities all on one floor. Paths are mainly gravel, and on a slight incline to the terrace and a further pathway to the pool.

The very large terrace, the garden and swimming pool has plenty of discrete lighting to enjoy the surrounds and its facilities

Additional facilities in the area are tennis courts, horse riding, as well as the many local festivals

Additional services are available on request - including maid, chef, guides and so on


  • Air Conditioning
  • Apple TV
  • Children Welcome
  • Linens and Towels Provided
  • Mosquito nets on windows
  • Private Pool
  • Washing Machine
  • Wi Fi
  • Coffee maker
  • Family holidays
  • Garden
  • Hair Dryer
  • Kitchen facilities - Full kitchen
  • Non Smoking
  • Toaster
  • barbecue
  • Parking Free
  • wheelchair accessable
  • Pet friendly -please ask


What our guests have had to say:

Verified Up Front Reviews
A group of friends wanted a peaceful and experience in Tuscany - preferably with the visions conjured up from holiday programes of Tuscan's famous countryside and hill top towns. Finding Castello was therefore a real find. THe views - wonderful, the pool and terraces providing plenty of space to enjoy the views. The main villa (with two bedrooms and two bathrooms) full of detail and thoughtful touches in the kitchen and elsewhere. The studio /annex caused some argument - as we all wanted to enjoy it (A bedroom, separate bathroom, sitting room and kitchenette plus a lovely shaded breakfast table). Besides the tranquility of the house, pool, terraces, gardens etc - there are all the wonderful hill towns to visit - including a great day out in Florence by train form the local town Very, very enjoyable


Verified Up Front Reviews
Compared to the price we paid, we would have liked a little more service than we got. No hot water or heating for 7 days. Waited 2 days for the laundry key. When we said there wasn't´t any key, we were told that there was...quite rudely. The owner was very nice, but didn't´t speak english, so we were forced to communicate through the concierge, who was very arrogant, and sometimes even hostile towards us. Anyway the place was fantastic and the location quite unique..

Jacob Christoffersen

Verified Up Front Reviews
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 .


Verified Up Front Reviews
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


Verified Up Front Reviews
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.


Verified Up Front Reviews
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 -


Verified Up Front Reviews
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.


Verified Up Front Reviews
We very much enjoyed our stay at Villa Roccolo. We would definitely recommend this to others! Pro's: - 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!

George and Aukelien Dimitriu

Verified Up Front Reviews
this was a good find. for our family - perfect. the main villa big enough for our family of 6 to enjoy - but having the seperate annex for our parents to have independent bedtoom, bathroom and sitting room made it so enjoyable. clearly great care in the renovation and the "little things" that make a far away vacation - that much more enjoyable. The helpful agent who lives close by helper with our daily tours and the owners welcome pack a nice surprise comfortable, clean, great (fantastic) location and, very much appreciated thank you !


Verified Up Front Reviews
Greeted upon arrival by representative of Tuscan Charm, Terry and the property owner, Rosano, who were both very pleasant and informative about the property and also the surrounding area and associated attractions. If we had any issue what so ever they were straight back to us to ensure we were ok. The property itself was fantastic, it has quite a steep drive but easily accessible on the side or a hill just outside the local hill top town, the owner has really put a huge amount of effort into restoring and rebuilding the property with original features. The pool was great and very clean although a bit cool in September, which is to be expected for the time of year. Would be fantastic in the full heat of Summer though and children would love it. Quite possibly the most relaxing location we've been to, you could literally hear a pin drop on most occasions. The views from the property were breathtaking and exceptional, from sunset to sunrise!!! Rich and Claire, Tattenhall, Cheshire

Rich and Claire Howe

Villa Castello Roccolo Location in Tuscany

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