Holiday homes - Holiday rentals

Close

View larger map

Also consider

Europe Holidays
419302 properties
Italy Holidays
101462 properties
Tuscany Holidays
24841 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Pieve di Chio
10 properties
Brolio
10 properties
Castroncello
6 properties

Castiglion Fiorentino

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

67 Holiday homes

Filters applied: Pets allowed (67)

(13) Excellent 

21

Holiday cottage in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 27 km
  • Swimming pool
  • Suitable for children age 5+
“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.  …see more

from £106 / night

£611 - £674 / week

Enquire View

from £106 / night

44

Holiday farmhouse in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Brolio Quinto is the ideal location for a peaceful holiday in the warm atmosphere of an old country farmhouse, beautifully preserved in its original architectural style. You can rent the top floor of this historic farmhouse with its independent access. It sleeps 8 +  …see more

from £128 / night

£1145 - £1314 / week

Book View

from £128 / night

21

Holiday villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely stone villa is located on the hills between Arezzo (18km) and Cortona (12km), only few minutes from Castiglion Fiorentino (3km), a lovely medieval village dominating the green valleys of the Val di Chio and the Val di Chiana. This strategic position offers  …see more

from £255 / night

£1272 - £2543 / week

Book View

from £255 / night

(9) Very Good 

33

Holiday cottage with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 26 km
  • Swimming pool
  • Suitable for children age 5+
“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  …see more

from £115 / night

£634 - £717 / week

Enquire View

from £115 / night

(5) Excellent 

15

Holiday apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 25 km
  • Swimming pool
  • Child friendly
“Absolutely gorgeous!” We had the best time at Maria's beautiful place! Very nice apartment with two large and bright bed rooms, fans and mosquito nets at the windows (yeah!!). The surroundings were absolutely stunning, situated among wineyards and oli  …see more

from £81 / night

£562 / week

Enquire View

from £81 / night

(4) Excellent 

48

Holiday villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
ENCHAINTING VILLA with private POOL on top of TUSCAN HILLS. 10 minutes drive to the town of Castiglion Fiorentino. 25 to CORTONA. One hour to FIRENZE, PERUGIA and SIENA. 30 minutes to the TRASIMENO LAKE.  …see more

from £102 / night

£636 - £1187 / week

Book View

from £102 / night

(7) Very Good 

18

Castiglion Fiorentino holiday villa rental

Province of Arezzo / Castiglion Fiorentino

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“AMAZING!!!” I've had the most wonderful stay in this Tuscan gem! Jacopo is such a great host and was always there to answer my questions. The villa is just beautiful! Each room and corner has something unique about it. The gardner Giancarlo came to ma  …see more

from £170 / night

£1187 - £2289 / week

Book View

from £170 / night

(1) Excellent 

15

Castiglion Fiorentino / Montecchio Vesponi

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Nearest beach 150 km
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

8

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £77 / night

£382 - £653 / week

Book View

from £77 / night

8

Province of Arezzo / Castiglion Fiorentino

13 5 Min stay varies

  • 13 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £47 / night

£297 - £551 / week

Book View

from £47 / night

18

Holiday home with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 23 km
  • Swimming pool
  • Child friendly
The freshness of this charming garden apartment offering space and easy access to many of Tuscany's hill towns, vineyards and festivals., makes it a good choice for families (or friends) looking for something special and a lovely home in Tuscany  …see more

from £84 / night

£585 / week

Enquire View

from £84 / night

11

Holiday villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 25 km
  • Child friendly
  • Ask about pets
Coppa di Sopra is an elegant and enchanting villa overlooking one of Tuscany's favorite valleys - “Coppa di Sopra is a magical place.  …see more

from £185 / night

£1289 / week

Enquire View

from £185 / night

(9) Excellent 

42

Holiday cottage with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 25 km
  • Swimming pool
  • Suitable for children age 5+
“Romantic, clean cottage, splendid view, lovely silence; unique location.” Whenever we plan a vacation we have following criteria in mind: comfortable, clean housing, privacy, far from all noise, nice view, close to cultural highlights, pleasant climat  …see more

from £106 / night

£615 - £700 / week

Enquire View

from £106 / night

(2) Excellent 

14

Holiday b&b in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about pets
tuscany, agriturismo, cortona, Arezzo, Castiglion FiorentinoWithin 550 meters is a local bar and grocery store. The medieval town of Castiglion Fiorentino is about 5 km  …see more

from £77 / night

£467 / week

Book View

from £77 / night

14

Holiday villa in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Holiday property located in Tuscany in Castiglion Fiorentino. Close location to many touristic attractions like Cortona, Arezzo, Siena, Montepulciano, Montalcino, Chianti, Florence and many more makes it a fantastic place for family holidays.  …see more

from £300 / night

£2094 / week

Enquire View

from £300 / night

12

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from £68 / night

£297 / week

Book View

from £68 / night

11

Castiglion Fiorentino / Orzale

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

(2) Very Good 

16

Holiday apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“A warm welcome and a great time for us” We are late to thank Maria and Terry for their help in making our vacation plans and for their warm welcome. Our cottage/apartment here was just what we expected -clean, comfortable and fantastic views - from  …see more

from £83 / night

£581 / week

Enquire View

from £83 / night

(6) Excellent 

12

Holiday home with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
“Charming, comfortable country villa, conveniently located.” Charming villa, comfortably accommodates 12 adults. Can be divided into 3 separate 2-bedroom apartments, each with its own kitchen/dining/bath and living area, or rented as one for use by a g  …see more

from £424 / night

£2967 / week

Book View

from £424 / night

(1) Very Good 

21

Holiday cottage with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
“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

from £84 / night

£589 / week

Enquire View

from £84 / night

(1) Excellent 

20

Apartment rental in Castiglion Fiorentino with shared pool

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax and beautiful view  …see more

from £47 / night

£323 - £609 / week

Book View

from £47 / night

14

Holiday home with shared pool in Pieve di Chio

Castiglion Fiorentino / Pieve di Chio

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 22 km
  • Swimming pool
  • Child friendly
A quiet and charming setting for you to enjoy country living. Cottage Grande is part of a working organic farm or agriturismo. It offers a real taste of the Tuscan traditions along with all the modern comforts you will appreciate for your family vacation.  …see more

from £120 / night

£835 / week

Enquire View

from £120 / night

19

Castiglion Fiorentino holiday apartment rental

Province of Arezzo / Castiglion Fiorentino

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Exceptional value for family holiday in Tuscany. Bright, modern, clean and easy to access. Two bedrooms, two bathrooms and lots of space inside and out.  …see more

from £101 / night

£704 / week

Enquire View

from £101 / night

25

Holiday villa with swimming pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £88 / night

£611 - £992 / week

Book View

from £88 / night

26

Villa rental in Castiglion Fiorentino with swimming pool

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
It is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £85 / night

£594 - £1136 / week

Book View

from £85 / night

38

Castiglion Fiorentino holiday villa rental

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere San Martino is an ancient farm of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio nearby the Historical towns of Castiglion Fiorentino ( 10 min. ), Cortona ( 20 min. ), Florence ( 1 hour ), Siena ( 1 hour ), Perugia ( 1 h  …see more

from £102 / night

£636 - £2204 / week

Book View

from £102 / night

17

Holiday apartment with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax and beautiful view  …see more

from £54 / night

£373 - £695 / week

Book View

from £54 / night

20

Castiglion Fiorentino holiday apartment rental

Province of Arezzo / Castiglion Fiorentino

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax  …see more

from £37 / night

£255 - £465 / week

Book View

from £37 / night

36

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £97 / night

£678 - £1119 / week

Enquire View

from £97 / night

(4) Excellent 

9

Province of Arezzo / Castiglion Fiorentino

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £56 / night

£386 / week

Book View

from £56 / night

(1) Excellent 

33

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £170 / night

£1017 - £2204 / week

Book View

from £170 / night

34

Province of Arezzo / Castiglion Fiorentino

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £55 / night

£382 - £560 / week

Enquire View

from £55 / night

(4) Excellent 

48

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £102 / night

£636 - £1187 / week

Book View

from £102 / night

9

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £146 / night

£1017 - £1526 / week

Enquire View

from £146 / night

7

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £124 / night

£865 - £1289 / week

Enquire View

from £124 / night

(1) Very Good 

7

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £93 / night

£645 - £916 / week

Enquire View

from £93 / night

99

Province of Arezzo / Castiglion Fiorentino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 27 km
  • Swimming pool
  • Child friendly

 …see more

from £212 / night

£1568 - £1865 / week

Book View

from £212 / night

30

Province of Arezzo / Castiglion Fiorentino

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £139 / night

£967 - £2707 / week

Enquire View

from £139 / night

22

Province of Arezzo / Castiglion Fiorentino

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £167 / night

£1212 - £2382 / week

Book View

from £167 / night

23

Castiglion Fiorentino / Pieve di Chio

6 15 7 nights min

  • 6 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £238 / night

£1662 - £4233 / week

Enquire View

from £238 / night

Top Destination reviews

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 … see more
Casa Dei Sogni, Tuscan Villa, Private Pool, A/C
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 … see more
Tuscany cottage with Private Pool, BBQ, & Parking
The Trip of a Lifetime!!

This was a beautiful experience! The house was out in the country but not too far away from all of the activities and conveniences. It was beautiful at night! A million stars and so very quiet! It was up on a hill so the view was lovely; vineyar … see more