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Castiglion Fiorentino Rentals

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3,458 Houses

Tuscany Villa Bellavista

Castiglion Fiorentino villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$152

MAS THE LEADER OF HOLIDAY HOUSE

Castiglion Fiorentino villa

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 27 minutes

Price per night from

$379

Villa Magnifica

Brolio villa

9 bedrooms / 11 bathrooms / sleeps 24

Price per night from

$749

Tuscany Villa Principe

Castiglion Fiorentino villa

5 bedrooms / 10 bathrooms / sleeps 10

Price per night from

$265

Borgo Tranquilitta - IL SOLE - Family Cottages in Tuscany with pool.

Castiglion Fiorentino cottage

2 bedrooms / 1 bathroom / sleeps 4

“Enjoyable family Vacances” we liked very much our cottage here. it was nicely arranged with all things we needed. excellent views from garden and pool. friendly owners to help us with plans. we also made new freinds too.

Responds fast! avg. 2 hours 35 minutes

Price per night from

$137

TUSCANY VILLA PRINCIPE 8 prsns

Castiglion Fiorentino villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$227

Dreamful rooms or apartments in the heart of Tuscany

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 27 minutes

Price per night from

$152

Villa Castello Roccolo - Tuscan Borgo With fabulous views, Perfect for 6 guests

Castiglion Fiorentino villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$347

4 bedroom, Restored Farmhouse, Modern Amenities

Castiglion Fiorentino cottage

4 bedrooms / 3 bathrooms / sleeps 8

“Lovely time at Castiglion Fiorentino” We stayed in the ground floor apartment, which was very clean and tastefully decorated. There was a swimming pool, which we had virtually to ourselves, but would have been shared by others in the adjacent barn conversion. There was lots of wildlife in the nearby field (tiny ghekos and lizzards on the patio, wild boar, etc) to view from our balcony, overlooking the field. This provided endless entertainment for our two boys (7 and 8 years old). We will probably return next year. The only draw-back was the location was not so easy to find, so check-in was not straight-forward, bit of an adventure.

Price per night from

$171

Villa Margarita, Spacious Tuscan Family home with lovely Pool

Castiglion Fiorentino villa

6 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$486

CASA PELEGRINI , 4 BEDOOM FARMHOUSE

Castiglion Fiorentino villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 35 minutes

Price per night from

$196

Large Tuscan Villa, Private Pool, Gardens and views

Castiglion Fiorentino villa

5 bedrooms / 3 bathrooms / sleeps 11

“this could be heaven!” 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, fantastic people and fantastic vacation.

Price per night from

$309

Agriturismo Le Maceie Tuscan Vacation Rental

Castiglion Fiorentino house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$82

Luxury Tuscan Villa, Villa Francesca, Cortona Tuscany

Castiglion Fiorentino apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$572

Villa Nonna, Great Value Family Villa

Castiglion Fiorentino apartment

4 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 2 hours 35 minutes

Price per night from

$615

Casa Serena, Private Cottage and Pool - Charming Private Cottage with Private Pool , and Views

Castiglion Fiorentino cottage

2 bedrooms / 1 bathroom / sleeps 4

“You'll love it here - totally relaxing Tuscany” 14 wonderful days at Casa Serena and wish we were back. Terry was a wonderful stand-in host (on behalf of the owners) and made us feel like welcomed family. The cottage is cozy and well appointed. The property is clean, rustic but charming and you can immediately feel the Tuscan life-style. Two good size bedrooms - one double with amazing views and the second arranged with twin beds with a view of the olive grove. Comfy beds, plenty of storage space. A large sitting room (although we spent all of our time on the outside terrace and gardens). The views are amazing and the private pool is the perfect venue on the hot summer days. Lots of things to do and see within half and hour to an hours drive. Loved being in a place that was so private and yet close enough for shopping and restaurants. There are a couple of local markets not to be missed. Castiglion on Fridays, Camucia (Cortona) Thursday (really good) and Cortona on Saturday. Perfect fresh produce to bring home and prepare a great Italian dinner. We used the small barbecue for many of our meals here, but the kitchen is well equipped access to the house is via a main and white road - about 2 km to the shop (nice croissants in the morning) and nearest restaurant. It was (for us) an easy drive and the views - especially coming down the hill are just wonderful. For us this was a lovely experience and as we hope to come back one day - you `LL love it here!!!

Responds fast! avg. 2 hours 35 minutes

Price per night from

$232

Podere le Spighe

Castiglion Fiorentino b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$101

Cottage maltilde - Casa Matilde. Family Home for 3-4 guests. Private Pool.

Castiglion Fiorentino cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 35 minutes

Price per night from

$181

Big & Bright Studio in Tuscany near Cortona - WiFi

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$76

Villa La Pinetina

Castiglion Fiorentino villa

10 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$457

Villa Coppa - 3 bedroom , 3 bathroom Private Villa, set in its own 25 acres of Tuscan landscape.

Castiglion Fiorentino villa

3 bedrooms / 3 bathrooms / sleeps 6

“A terrace on Tuscany” Beautiful old farm house, restored with care and respect, nicely furnished in a funny mix of old and new, great caracter. The garden offers variety of settings and great views. The location is ideal to tour, Cortona, Arezzo and many nice little towns around. Simply charming !

Responds fast! avg. 2 hours 35 minutes

Price per night from

$225

Villa Margarita - Large Family Villa - Tuscan Villa with pool and privacy

Castiglion Fiorentino apartment

6 bedrooms / 6 bathrooms / sleeps 13

Responds fast! avg. 2 hours 35 minutes

Price per night from

$477

Holiday House Traquandi

Castiglion Fiorentino house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$124

Villa Castiglioni - Castiglioni Villa, Private villa and pool, Air Conditioning for 12 plus

Castiglion Fiorentino villa

6 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 2 hours 35 minutes

Price per night from

$497

Villa Grande, Toscana - Tuscany independent villa, in quiet and charming settin

Castiglion Fiorentino cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$325

Large Studio apartment in Historical Centre - WiFi

Castiglion Fiorentino apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$93

Borgo Tranquilitta - THE STAR

Castiglion Fiorentino cottage

2 bedrooms / 1 bathroom / sleeps 4

“Top value, an enjoyable experience” We all agreed, nice cottage. everything you need, you find in the kitchen. very nice pool 30 meters from the cottage. Perfect customer service from the owner incl. information about the traveling and the places of interest. lovely and quite place, we enjoyed our short stay very much. Top

Responds fast! avg. 2 hours 35 minutes

Price per night from

$156

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

Castiglion Fiorentino house

9 bedrooms / 9 bathrooms / sleeps 18

Price per night from

$669

Villa Angelisa C

Castiglion Fiorentino apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 10 minutes

Price per night from

$146

Villa MIchelangelo

Brolio house

9 bedrooms / 11 bathrooms / sleeps 18

Price per night from

$747

Exclusive , Luxury Tuscan Vacation Home.

Castiglion Fiorentino villa

6 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$404

Villa Angelisa A

Castiglion Fiorentino apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 10 minutes

Price per night from

$117

Villa Michelangelo

Brolio villa

9 bedrooms / 11 bathrooms / sleeps 18

Price per night from

$600

Borgo Santa Lucia studio apartment

Castiglion Fiorentino house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$80

Villa Rustica

Castiglion Fiorentino house

9 bedrooms / 9 bathrooms / sleeps 18

Price per night from

$479

Casa Santa Lucia, Noto Barocca

Castiglion Fiorentino house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$84

Villa Angelisa D

Castiglion Fiorentino apartment

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 10 minutes

Price per night from

$146

VILLA PRINCIPE WITH POOL 6 SLEEPS

Castiglion Fiorentino villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$215

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rentals in Castiglion Fiorentino

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About Castiglion Fiorentino

Millions of people come to visit Tuscany every year, but a stay in the quiet village of Castiglion Fiorentino, where beautiful countryside and mountains surround you everywhere you turn, is a great way to get the Tuscan experience without enduring throngs of visitors. You'll find most of the top restaurants in town and trendy boutique shopping along Via Nazionale, the main street in Castiglion Fiorentino. Several stunning old buildings can also be found on the street known as Via Vecchie Ciminiere.

Here are some of the other must-see attractions and activities in the area:

  • Castello di Fiorentina: This nearby village is surrounded by great architecture and offers picturesque views of the countryside.
  • Try the Cuisine: The food in this part of Tuscany is simple, yet full of flavor. Try the Panzanella, a delicate ravioli made in a rich truffle sauce.
  • Apennine Mountains: These mountains offer walking and hiking trails that take you past the olive trees that the area is famous for.
  • Church of Saint Angelo: The most popular church in Castiglion Fiorentino dates back to the 12th century and is one of the many ancient structures in the middle of the historical center.
  • Play Golf: Several golf courses for all levels of players have sprung up in recent years throughout the area. Casentino Golf Club is the most popular amongst the locals.

It doesn't matter when you decide to Castiglion Fiorentino because the Fiera Antiquaria is one of the many events that take place year-round. Held on the first Sunday of every month, people from all over Italy come to look at clothing and locally made food and crafts from over 500 vendors. Some of the other major events in the area include the horse race in June known as the Palio dei Rioni and Giostra del Sacarino an equestrian competition in nearby Arezzo that has been held every June for over 400 years.

The Tuscan region is one of the most popular vacation spots in the world, which means that there is no shortage of vacation rentals available year-round. Book a condo that overlooks the vineyards and beautiful countryside, or rent a property downtown near the restaurants and shopping.

A vacation to Castiglion Fiorentino wouldn't be complete without visiting some of the nearby cities and towns that make this area so popular. If you have some extra time to explore, plan a day trip to the world-renowned art on display in the town of Arezzo or the canals and historical attractions of Florence, both which can be reached within 30 minutes by car.

Top Destination reviews

Large Tuscan Villa, Private Pool, Gardens and views
Perfect family celebration in Tuscany

This review is a little late, but the experience we had is well worth taking the time to write it. My wife and I were trying to find a place to relax and enjoy our 25th anniversary with our family and we couldn't have found a better spot. The grounds and property are amazing, with a private pool enjoy all to ourselves. The pool terraces and out kitchen very cozy and had everything we needed to just relax and enjoy the real Tuscany. With everything so close including wineries and restaurants, there was plenty to keep us busy when we went sight seeing. But, the best part about it, is that some of us didn't want to leave the villa - simply relaxing by the pool and just enjoying the endless scenery and villa - a vacation in itself. For our "big Day" we arranged for a local chef to come along and prepare the most awesome lunch for us all. Everything from canapés to a fabulous cake - We were spoilt! We can easily highly recommend this vacation home if your looking to enjoy either Tuscany's countryside,go touring or, simple enjoy living in an amazing Tuscan villa that will make you want to return - before another 25 years! . Thank you Gerry for all that you did to make our trip a great experience!see more
Villa la Foce: breathtaking panoramic view
Perfection

Villa la Foce is amazing! And I am very fussy! This home is immaculate and the gardens and pool area are superb. We arrived via the newer part of the village and were initially concerned that it did not have the charm we were after... A drive through the old village and up the hill put our concerns to rest! The view is breathtaking and sipping prosecco while cooking homemade pizza in the wood fired oven while the children swam and laughed in the balmy twilight will never be forgotten! We spotted wild boar in the olive grove below the house, pheasant, badgers, squirrels and even a scorpion scurried out of the pizza oven when lit! All a novelty for this australian family! The restaurant at the top of the hill "la Foce" was recommended by our helpful key holder Enrico... Fabulous food - try the Chianina Bistecca and wonderful service. The famous Palio was on in the village during our stay and was wildly entertaining. We were well positioned to explore Tuscany and loved being out of the village but not too far away. We would return in a heartbeat and thank both the owners for sharing such a beautiful property and terretrushe for the excellent service! We hope to return one day. Bellisimo ! The Foster Family.see more
Borgo Tranquilitta - IL SOLE - Family Cottages in Tuscany with pool.
Relaxing and enjoyable family holiday

Our cottage, Le Stelle, (the stars) was perfect for the four of us (we and. our children 10 and 13 ). The cottage was comfortable clean and tidy. our private terraces were also perfect for us to enjoy outside eating and as a quiet spot to read or - little work (sorry) as it has good Wifi. The children enjoyed the company of the others in the adjacent cottages and we parents also had time for ourselves. The pool was the main meeting place, lots of seating and sun loungers and big enough for us all to enjoy. Besides a huge pizza/stone oven we each had our own barbecues. Only one of our neighbours used the large oven - for pizza warming! The area offers many attractions,, fairs and patents. Cortona and Castiglion Fiorentino had a medieval fair and in arezzo there was a huge antiques/flee market which we managed on the way back to Pisa airport. The local restaurants - all family friendly and serving excellent local food. The hosts played an important part. Their English rep was on hand if needed (a phone call away) and for us this was very helpful as he helped plan a day to Florence - without having to queue - thank you terry. There were also a coup,e of issues with a few things missing (a cork screw and a lightbulb), but he had both sorted very quickly. A very pleasant spot to relax and enjoy the country life of Tuscany. Great views and sunsets all worth while (even if the white road was a little long at first), and the great walks around the area too.see more
Borgo Tranquilitta - THE STAR
A cosy place for our family holiday

This place has a perfect setting. grand countryside and perfect sunsets. Besides the (partial) bumpy road, we really enjoyed our stay here. Our stay enhanced by the other guests staying in the 2 other cottages. We each had our own space, but were able to enjoy each others company - especially the kids. The place offers comfort and a sense of well being in Tuscany's countryside. We enjoyed the pool, the long walks around the property ( even catching a glimpse of a wild boar and its family towards the church that is well hidden fat the very top of the hill ) and returning home for a barbecue or just to relax a special thank you to the owner and to Terry for helping us with a trip to the doctor and for dealing with translation and , just being there for us. A few hours of their time was very kind The local shop is also worth a mention. Good fresh cheese, salami etc along with all we needed for quick supplies. This is open on Sunday morning so very useful for that important item (s) we forgot to buy at the market in saturday.see more
Borgo Tranquilitta - LA LUNA
great family vacation

For our small family gathering, this proved to be a great place. We had both cottage Luna and Stelle, giving us independence as well as being close for each other. We really enjoyed this lovely place and stunning views and surrounds. Very peaceful and a totally relaxing setting - especially the pool. The owners gave us the additional studio with large dining table which was useful for the one rainy day. If you are looking for somewhere to get away from it all and just relax quietly this is the place for you. We also found it accessible for groceries, (small simple Italian village shop and bar about 2 km), but also not too far for sightseeing the small hill towns and as well as an easy day trip by train to Florence.(One minor thing though was our initial experience of the road, a little bumpy after the rains, but it was Ok the second time and better the third) The place has lots of old time characteristics everywhere you look which added to the fun of the place and gave us a real taste of Tuscan country living. . The old fashioned pizza oven was great too - even though we used it for reheating our bought pizza from the town. This property exceeded our expectations, and the owner/agent was warm and hospitable. We would certainly return when we next visit Italy, and if, like us, this is your first time you will not be disappointed.see more
Villa Coppa - 3 bedroom , 3 bathroom Private Villa, set in its own 25 acres of Tuscan landscape.
A beautiful Tuscan Experience

What greeted us on our arrival was a beautiful view over the olive studied hill, absolutely stupendous. The house is very comfortable and furnished in a chic way. Beds, often with antique bedsteads are so comfortable you never want to get up. And the loggia with long table under the stars for dinner is wonderful. This area is beautiful and convenient. We live in Italy part of the time, so we know it well. Cortona and arezzo are 15-20 minutes away, and all the hill towns are close by. Castiglion Fiorentino, the town at the bottom of the hill is the perfect size for exploring on foot and, best of all, but not well known is that you can part at the local train station free of charge and take the train to Florence, thereby avoiding the scary driving and the equally scary parking in Florence. This lovely home really does rate 5 stars.see more

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