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

2,860 Holiday homes

Holiday home with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino house

9 bedrooms • 9 bathrooms • sleeps 18

from £380 / night

£2,658 - £5,317 / week

1 / 17

Holiday apartment in Castiglion Fiorentino

Castiglion Fiorentino apartment

4 bedrooms • 3 bathrooms • sleeps 8

Pricing unknown

1 / 4

Home rental in Castiglion Fiorentino with swimming pool

Castiglion Fiorentino house

4 bedrooms • 4 bathrooms • sleeps 8

from £369 / night

£2,580 - £3,535 / week

1 / 14

Castiglion Fiorentino holiday home accommodation

Castiglion Fiorentino house

4 bedrooms • 5 bathrooms • sleeps 8

from £369 / night

£2,580 - £3,535 / week

1 / 19

Holiday home in Pieve di Chio

Pieve di Chio house

2 bedrooms • 2 bathrooms • sleeps 4

from £151 / night

£1,051 - £1,433 / week

1 / 8

Castiglion Fiorentino holiday villa rental

Castiglion Fiorentino villa

2 bedrooms • 2 bathrooms • sleeps 4

from £115 / night

£717 / week

1 / 48

Holiday villa in La Strada-Santa Cristina

La Strada-Santa Cristina villa

8 bedrooms • 6 bathrooms • sleeps 20

from £355 / night

£2,484 - £3,535 / week

1 / 20

Holiday apartment with shared pool in Castiglion Fiorentino

Castiglion Fiorentino apartment

1 bedroom • 1 bathroom • sleeps 4

from £134 / night

£937 / week

1 / 31

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

5 bedrooms • 3 bathrooms • sleeps 11

from £359 / night

£2,656 / week

1 / 79

Holiday farmhouse with shared pool in Castiglion Fiorentino

Castiglion Fiorentino farmhouse

13 bedrooms • 1 bathroom • sleeps 5

from £58 / night

£363 / week

1 / 8

Holiday b&b in Castiglion Fiorentino

Castiglion Fiorentino b&b

1 bedroom • 1 bathroom • sleeps 2

from £158 / night

£1,104 / week

1 / 11

Holiday home with swimming pool in Montecchio Vesponi

Montecchio Vesponi house

4 bedrooms • 3 bathrooms • sleeps 11

Pricing unknown

1 / 21

Castiglion Fiorentino holiday home rental

Castiglion Fiorentino house

2 bedrooms • 1 bathroom • sleeps 4

from £48 / night

£335 / week

1 / 16

Holiday home with indoor pool in Brolio

Brolio house

9 bedrooms • 11 bathrooms • sleeps 18

from £566 / night

£3,171 - £6,008 / week

1 / 171

Holiday apartment rental

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 4

from £58 / night

£402 / week

1 / 27

Castiglion Fiorentino holiday apartment rental

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 4

from £88 / night

£533 - £788 / week

1 / 33

Holiday villa with indoor pool in Brolio

Brolio villa

9 bedrooms • 11 bathrooms • sleeps 18

from £568 / night

£3,171 - £6,008 / week

1 / 63

Castiglion Fiorentino holiday apartment rental

Castiglion Fiorentino apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £110 / night

£670 - £980 / week

1 / 29

Holiday apartment in Castiglion Fiorentino

Castiglion Fiorentino apartment

1 bedroom • 1 bathroom • sleeps 3

from £110 / night

£516 / week

1 / 11

Holiday apartment rental

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 4

from £72 / night

£502 / week

1 / 12

Holiday villa with swimming pool in Pieve di Chio

Pieve di Chio villa

2 bedrooms • 2 bathrooms • sleeps 6

from £117 / night

£811 - £1,532 / week

1 / 43

Holiday apartment with shared pool in Castiglion Fiorentino

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 4

from £88 / night

£533 - £788 / week

1 / 28

Apartment rental in Castiglion Fiorentino with shared pool

Castiglion Fiorentino apartment

2 bedrooms • 2 bathrooms • sleeps 7

from £110 / night

£670 - £980 / week

1 / 31

Castiglion Fiorentino holiday villa rental

Castiglion Fiorentino villa

7 bedrooms • 9 bathrooms • sleeps 14

from £410 / night

£2,866 - £4,300 / week

1 / 49

Pieve di Chio holiday farmhouse rental

Pieve di Chio farmhouse

1 bedroom • 1 bathroom • sleeps 4

from £63 / night

£379 - £693 / week

1 / 26

Holiday farmhouse with shared pool in Pieve di Chio

Pieve di Chio farmhouse

1 bedroom • 1 bathroom • sleeps 4

from £63 / night

£385 - £693 / week

1 / 31

Apartment rental in Castiglion Fiorentino with shared pool

Castiglion Fiorentino apartment

1 bedroom • 1 bathroom • sleeps 2

from £234 / night

£1,639 / week

1 / 16

Holiday villa rental

Santa Margherita villa

5 bedrooms • 3 bathrooms • sleeps 10

from £338 / night

£2,361 / week

1 / 30

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

7 bedrooms • 9 bathrooms • sleeps 18

from £669 / night

£4,300 / week

1 / 59

Home rental in Castiglion Fiorentino with shared pool

Castiglion Fiorentino house

1 bedroom • 1 bathroom • sleeps 3

from £92 / night

£631 - £863 / week

1 / 36

Castiglion Fiorentino holiday villa rental

Castiglion Fiorentino villa

3 bedrooms • 3 bathrooms • sleeps 8

from £177 / night

£1,238 / week

1 / 26

Gaggioleto holiday home rental

Gaggioleto house

4 bedrooms • 3 bathrooms • sleeps 12

from £250 / night

£1,576 - £2,894 / week

1 / 34

Holiday apartment in Castiglion Fiorentino

Castiglion Fiorentino apartment

2 bedrooms • 1 bathroom • sleeps 4

from £67 / night

£469 / week

1 / 12

Holiday home rental

Pieve di Chio house

6 bedrooms • 6 bathrooms • sleeps 15

from £270 / night

£1,691 - £3,774 / week

1 / 44

Pieve di Chio holiday farmhouse rental

Pieve di Chio farmhouse

2 bedrooms • 4 bathrooms • sleeps 14

from £277 / night

£1,651 - £2,665 / week

1 / 40

Holiday villa with swimming pool in Castiglion Fiorentino

Castiglion Fiorentino villa

7 bedrooms • 7 bathrooms • sleeps 15

from £338 / night

£2,361 / week

1 / 51

Home rental in Castiglion Fiorentino with swimming pool

Castiglion Fiorentino house

5 bedrooms • 3 bathrooms • sleeps 9

from £222 / night

£1,467 - £2,472 / week

1 / 39

Castiglion Fiorentino holiday villa rental

Castiglion Fiorentino villa

4 bedrooms • 5 bathrooms • sleeps 8

from £246 / night

£1,720 - £3,000 / week

1 / 23

Cottage rental in Castiglion Fiorentino with shared pool

Castiglion Fiorentino cottage

2 bedrooms • 1 bathroom • sleeps 5

from £115 / night

£765 - £965 / week

1 / 35

Brolio holiday villa rental

Brolio villa

9 bedrooms • 11 bathrooms • sleeps 24

from £568 / night

£3,171 - £6,008 / week

1 / 55

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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

Restored Tuscan Cottage near Cortona with Infinity Pool, Outside Kitchen & BBQ
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

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