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Villas in Castiglion Fiorentino and Apartments – Holiday Lettings - Holiday Rentals Castiglion Fiorentino

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3,679 Holiday homes

Holiday home with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino house

6 bedrooms • 5 bathrooms • sleeps 13

7 reviews

from £513 / night

£3,591 / week

1 / 12

Cottage accommodation in Pieve di Chio with swimming pool

Pieve di Chio cottage

2 bedrooms • 2 bathrooms • sleeps 6

17 reviews

from £142 / night

£990 / week

1 / 22

Castiglion Fiorentino holiday home rental

Castiglion Fiorentino house

2 bedrooms • 1 bathroom • sleeps 4

from £50 / night

£348 / week

1 / 16

Holiday farmhouse with shared pool in Castiglion Fiorentino

Castiglion Fiorentino farmhouse

13 bedrooms • 1 bathroom • sleeps 5

from £60 / night

£377 / week

1 / 8

Holiday apartment rental

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 6

4 reviews

from £89 / night

£563 - £700 / week

1 / 20

Villa rental in Castiglion Fiorentino

Castiglion Fiorentino villa

4 bedrooms • 4 bathrooms • sleeps 10

from £513 / night

£3,592 / week

1 / 44

Holiday villa in Castiglion Fiorentino

Castiglion Fiorentino villa

3 bedrooms • 3 bathrooms • sleeps 6

3 reviews

from £326 / night

£2,281 / week

1 / 14

Home rental in Castiglion Fiorentino with swimming pool

Castiglion Fiorentino house

3 bedrooms • 3 bathrooms • sleeps 8

from £411 / night

£2,873 / week

1 / 26

Holiday townhouse with shared pool in Castiglion Fiorentino

Castiglion Fiorentino townhouse

2 bedrooms • 3 bathrooms • sleeps 10

from £296 / night

£2,070 / week

1 / 17

Holiday condo with shared pool in Montecchio Vesponi

Montecchio Vesponi condo

2 bedrooms • 1 bathroom • sleeps 5

from £70 / night

£489 / week

1 / 14

Holiday b&b in Castiglion Fiorentino

Castiglion Fiorentino b&b

1 bedroom • 1 bathroom • sleeps 2

2 reviews

from £93 / night

£565 / week

1 / 14

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

4 bedrooms • 3 bathrooms • sleeps 8

from £444 / night

£1,598 - £2,861 / week

1 / 25

Holiday b&b in Castiglion Fiorentino

Castiglion Fiorentino b&b

1 bedroom • 1 bathroom • sleeps 3

from £82 / night

£523 / week

1 / 8

Villa rental in Castiglion Fiorentino with swimming pool

Castiglion Fiorentino villa

6 bedrooms • 6 bathrooms • sleeps 12

from £473 / night

£3,250 / week

1 / 28

Holiday villa rental

Castiglion Fiorentino villa

3 bedrooms • 4 bathrooms • sleeps 6

from £280 / night

£1,961 - £3,235 / week

1 / 33

Holiday villa with indoor pool in Brolio

Brolio villa

9 bedrooms • 11 bathrooms • sleeps 18

from £583 / night

£3,254 - £6,165 / week

1 / 63

Holiday apartment in Castiglion Fiorentino

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 5

2 reviews

from £78 / night

£546 / week

1 / 14

Holiday farmhouse letting

Castiglion Fiorentino farmhouse

2 bedrooms • 2 bathrooms • sleeps 6

from £128 / night

£892 / week

1 / 48

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

4 bedrooms • 3 bathrooms • sleeps 8

22 reviews

from £294 / night

£1,422 - £3,412 / week

1 / 61

Holiday home with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino house

3 bedrooms • 3 bathrooms • sleeps 8

4 reviews

from £491 / night

£3,432 / week

1 / 24

Castiglion Fiorentino holiday villa rental

Castiglion Fiorentino villa

7 bedrooms • 9 bathrooms • sleeps 14

from £421 / night

£2,941 - £4,412 / week

1 / 49

Apartment rental in Castiglion Fiorentino with shared pool

Castiglion Fiorentino apartment

1 bedroom • 1 bathroom • sleeps 2

2 reviews

from £103 / night

£719 / week

1 / 11

Holiday villa accommodation

Castiglion Fiorentino villa

2 bedrooms • 2 bathrooms • sleeps 6

from £82 / night

£359 / week

1 / 12

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

7 bedrooms • 9 bathrooms • sleeps 18

5 reviews

from £686 / night

£4,405 / week

1 / 59

Castiglion Fiorentino holiday apartment rental

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 4

1 review

from £72 / night

£503 / week

1 / 13

Holiday farmhouse in Castiglion Fiorentino

Castiglion Fiorentino farmhouse

4 bedrooms • 2 bathrooms • sleeps 9

3 reviews

from £206 / night

£1,441 / week

1 / 55

Holiday studio in Castiglion Fiorentino

Castiglion Fiorentino studio

Studio • 1 bathroom • sleeps 4

from £51 / night

£352 / week

1 / 6

Holiday apartment with shared pool in Castiglion Fiorentino

Castiglion Fiorentino apartment

1 bedroom • 1 bathroom • sleeps 3

1 review

from £124 / night

£862 / week

1 / 12

Holiday apartment with shared pool in Castiglion Fiorentino

Castiglion Fiorentino apartment

1 bedroom • 1 bathroom • sleeps 4

from £129 / night

£898 / week

1 / 11

Brolio holiday villa rental

Brolio villa

9 bedrooms • 11 bathrooms • sleeps 18

from £666 / night

£3,726 - £7,059 / week

1 / 68

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

9 bedrooms • 9 bathrooms • sleeps 18

from £445 / night

£3,103 - £4,450 / week

1 / 17

Villa rental in Castiglion Fiorentino

Castiglion Fiorentino villa

6 bedrooms • 4 bathrooms • sleeps 2

2 reviews

from £67 / night

£467 / week

1 / 15

Holiday home in Castiglion Fiorentino

Castiglion Fiorentino house

1 bedroom • 1 bathroom • sleeps 2

1 review

from £46 / night

£257 / week

1 / 20

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

5 bedrooms • 5 bathrooms • sleeps 12

from £185 / night

£1,287 - £3,192 / week

1 / 34

Pieve di Chio holiday villa rental

Pieve di Chio villa

2 bedrooms • 1 bathroom • sleeps 5

from £119 / night

£765 - £1,340 / week

1 / 39

Holiday villa with swimming pool in Pieve di Chio

Pieve di Chio villa

2 bedrooms • 2 bathrooms • sleeps 6

from £144 / night

£934 - £1,294 / week

1 / 50

Holiday villa with shared pool in Castiglion Fiorentino

Castiglion Fiorentino villa

1 bedroom • 1 bathroom • sleeps 3

from £68 / night

£595 - £793 / week

1 / 26

Holiday apartment with shared pool in Castiglion Fiorentino

Castiglion Fiorentino apartment

1 bedroom • 1 bathroom • sleeps 2

from £49 / night

£343 / week

1 / 19

Holiday apartment rental

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 4

from £77 / night

£539 / week

1 / 12

Holiday villa with shared pool in Castiglion Fiorentino

Castiglion Fiorentino villa

3 bedrooms • 4 bathrooms • sleeps 6

from £144 / night

£873 / week

1 / 21

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Castiglion Fiorentino holidays

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 flavour. 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 centre.
  • 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 venders. 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 holiday spots in the world, which means that there is no shortage of holiday 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 holiday 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

Tuscany cottage near Castiglion Fiorentino, with Private Pool, BBQ, & Parking
Stunning views

This cottage is better than the pictures. It has stunning views across the valley and is ideally placed to visit all the nearby hilltop towns. We particularly enjoyed Cortona and Montepulciano. We spent a lot of time in the gorgeous pool taking in the views. The pool house was great with a toilet and a fridge so cold drinks were within easy reach. The cottage had everything we needed including plenty of towels for the pool. We had a lot of Bbq,s although it was missing a large grill to fit into the slots so we had to improvise. I would give this cottage 5 stars apart from a couple of things. The weather was very hot when we were there and although there are fans provided they were noisy to keep on all night and it was too hot to not have them on. Maybe some mesh screens would help at the windows so you could keep them open. Make sure you take plenty of insect repellent as we ended up with a lot of bites, even when we had sprayed. I know this can’t be helped but there are a lot of dogs in the nearby houses who barked a lot especially between 7-8pm so this cottage was not always a tranquil spot.see more
Villa Margarita, Spacious Tuscan Family home with lovely Pool
Amazing villa, peaceful with stunning views. Perfect location!

We stayed at this villa last Summer. Despite some confusion over our arrival day the owners and family ensured the villa was prepared for us before we settled in. I believe we were the first people to stay in the villa and it was perfect for our family. The bedrooms were beautifully furnished and the views were truly fabulous. We were able to eat al fresco on the balcony or terrace. The pool and surrounding area were just stunning - perfect for a family. The location and vista were perfect. We had a hire car (required due to the location) and were able to visit local village and towns. We enjoyed Florence and Sienna for day trips. The town of Cortona was very special. All in all a great villa with accommodating owners who tried very hard to make our stay perfect.see more
Cottage maltilde - Casa Matilde. Family Home for 3-4 guests. Private Pool.
Peace and tranquility

We had a great time, the pool was most welcome and the peace and tranquility much appreciated (only noise was the chickens next door!). It is quite remote but the stars were great and we even saw a porcupine. … see more
Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool - set within a  small Tuscan borgo
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored are within easy reach. There is plenty to see and do or you can just relax and enjoy the stillness as you lounge by the pool. A good selection "of delightful restaurants around in which to sample wonderful Italian food and wines. Looking forward to revisiting the delights of Tuscanny from this well situated holiday home.see more
Borgo Tranquilitta - IL SOLE - Family Cottages in Tuscany with pool.
Looking forward to next time

We thoroughly enjoyed our holiday at Borgo Tranquillita. It is the perfect place to stay whether you use it as a base for travelling the eastern part of Tuscany or just for a relaxing time at the top of picturesque hill. Lots of space around the three cottages, the perfect place for our dog. lots of privacy for ourselves. The cottage is clean and comfortable, the kitchen has got everything it needs - basics, no fuss - , the Wi-Fi works. The pool is just a few steps away from the cottage and we spent a lot of time just there catching up on some books and relaxing. But we also made a few day trips to places like Cortona, Arezzo, Gubbio and Florence which can also easily be reached by car. Taking the train to Florence is more comfortable though. There are also a couple of nice restaurants in Castiglion Fiorentino - namely Il Passagio and Pietro are well worth a visit. Thanks to the owner and Terry in particular who were very friendly and obliging. We felt at home from day 1. This a the perfect place to unwind and we wouldn´t hesitate to return, we loved it! Until next time...see more
Borgo Tranquilitta - LA LUNA
Rustic charm and a five star pool with a breathtaking view

This was indeed a haven of peace high up in the hills with a lovely view across the valley to the hills on the other side. The well appointed cottages make you feel you are part of the local landscape and the pool and its surroundings are delightfully luxurious. There are plenty of interesting places to see nearby, including Castiglione Fiorentino and Cortana.see more

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