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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

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A perfect home in Tuscany for friends and families of up to 6 guests. The main villa houses 4 guests with the lovely independent studio just 10 meters away offers a complete suite for two guests, providing a unique and private experience to enjoy.

With both the infinity-edge pool and the vast terrace offering " WOW views, tranquillity and relaxation here are absolutely lovely". It is a place to enjoy with family and friends as well as a great base to explore all that Tuscany has to offer.

Completed with style and character, the villa has one of the best settings to enjoy peace, privacy, private pool, a- stunning 9-meter terrace - with incredible vistas. Another important feature here are the screened windows so that you can thoroughly enjoy the warm spring and summer evenings - without any disturbance,,, The villa also has good access to many Tuscan towns, villages, wineries, festivals and so on. The property has two parts, the main villa with 2 bedrooms, 2 bathrooms modern kitchen, sitting room, dining room and lots of space (Apple TV is also available). Plus, the exclusive studio apartment just 10 meters away, providing an additional private double bedroom, bathroom, sitting room and kitchenette, perfect for families and friends looking for additional independence on holiday.

This is being "at home" in Tuscany .. A wonderful place for family, friends, and possibility too for small weddings. (There is a small chapel in the grounds which has also been restored and can be used for small weddings, Renewal of Vows Anniversaries - exclusive to guests).

A recent review sums up the special features of Villa Roocolo

“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 circumvents 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 consists of two houses. The smaller one has one bedroom, with a king-size bed, bathroom and living space with a 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 ”


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


What our guests have had to say:

Verified Up Front Reviews
Easy communication with the owners and Thanks for allowing an early check-in, which was very helpful since we had a baby with us. They also set up a lovely crib for our 9 month old to sleep in upstairs which was fantastic. There were many staples/ in the house making things easier - soap, paper towels, washing detergent, salt, olive oil, etc. Plus a generous welcome gift of fruits, wine and Prosecco . The company was also very prompt and responsive with any questions when booking again making our arrival easy. The rooms combine lots of modern amenities but keeping all the charm of the original building Which was restored a few years ago. the pool, terrace and garden setting are just PERFECT, and with the reasonably warm weather in October was something we did not hope for.. Everyone has heard of the appeal of Tuscany, But Tuscany goes way beyond the obvious appeal of Pisa’s leaning tower, Florence galleries etc , the smaller towns here Castiglion Fiorentino, cortona, pienza, the lake, Assisi and Arezzo were each special day visits . Then the food festivals at weekends captured all the local traditions and we felt very welcome at these. Thanks too to our host for his great tips and guidance, to make out dream vacation even better....

Andrew Andrew

Verified Up Front Reviews
I left the default "OK" in place for each rating category because there are good and less good aspects regarding each. The villa is set high in the hills with a stunning, always-fascinating, never-to-forget view of the Val di Chiana -- and you can enjoy that view from a large, beautiful infinity pool. What's not to like? Enough that this otherwise should-be-slam-dunk isn't, which is a pity for such a fabulous natural setting. We very much enjoyed our six-week stayed, and definitely came to feel at home. But ... (i) There's neither AC nor sufficient screening of doors/windows on first floor and in one of the two bedrooms. (ii) Endless bugs and bug bites. (iii) Very dark inside -- insufficient lighting. (iv) Hunters and workmen compromise privacy. (v) Grounds around pool are unfinished. (vi) The steep, rocky, curving road up is treacherous, though we managed to arrive safely - not always without drama and struggle. (vii) The downside of the blissful views, pool, peace, and quiet is commercial isolation: have to travel at least 10 or 15 minutes to town to get basics (though there's one nearby convenience store). And NO CAB service from town to villa. Reasonably priced, so tough to complain strenuously; but given its strong pluses, it could be so much better with just a bit more attention to detail.

Michael Delaurentis

Verified Up Front Reviews
What a great location this villa has. Sitting on the terrace having a meal watching the sunset our sitting in the pool looking out over the valley made us feel privileged to be here in Tuscany. The local town of Castiglion and Cortona Corroborate well worth a visit. Great restaurants, churches and museums to see. For the more active hire a couple of mountain bikes (We cheated and got ebikes) and explore the numerous trails on the ridges and valleys surrounding the villa. There is a guide book in the local Tourist information office in Castiglion that had some routes. STEELS bike shop in Castiglion are great and will deliver and collect the bikes. Villa had reverting we how's for and we came back refreshed and enthused a putt returning to Tuscany soon.

Giles Scoble

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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