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20 Holiday homes

Filters applied: City breaks (20)

Travellers going to Castiglion Fiorentino are booking September dates now. Secure your holiday home today and have the perfect trip.

(2) Excellent 

1 / 24

Villa Vallibona - Castiglion Fiorentino villa sleeps 11

Province of Arezzo / Castiglion Fiorentino

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Nearest beach 128 km; Swimming pool; Child friendly ;
Villa Vallibona is situated in the midst of peace and greenery in the gentle hills between Castiglion Fiorentino and Cortona, among olive groves and fruit trees, in a splendid panoramic position. The extensive property includes the main villa and the pool. Villa Vallibo  …see more

from £183 / night

£1283 - £3077 / week

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from £183 / night

1 / 23

Province of Arezzo / Castiglion Fiorentino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

1 / 15

Castiglion Fiorentino / Montecchio Vesponi

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 150 km; Child friendly ; Car advised;
 …see more

Pricing unknown

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Pricing unknown

Featured properties

1 / 12

Casa Del Cuore - with courtyard & Free wifi - Castiglion Fiorentino guest house sleeps 3

Province of Arezzo / Castiglion Fiorentino

1 3 3 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Child friendly ; Ask about pets; Private garden;
Situated in the historic center of one of Tuscany's most beautiful walled medieval villages, this independent home is nestled in the historic center of the once fortified village of Castiglion Fiorentino. Offering privacy and serenity with views of the Valdichiana  …see more

from £52 / night

£342 / week

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from £52 / night

1 / 21

CASOLARE IL CONDOTTIERO - Montecchio Vesponi house sleeps 11

Castiglion Fiorentino / Montecchio Vesponi

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Beautiful rural home placed on the silver hills covered with olives groves between Castiglion Fiorentino and Cortona, in a very panoramic position and a stone's throw away from the magnificent medieval castle of Montecchio Vesponi. The villages of Castiglion Fioren  …see more

from £106 / night

£684 - £1753 / week

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from £106 / night

1 / 11

Castiglion Fiorentino / Orzale

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

Pricing unknown

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Pricing unknown

1 / 24

Province of Arezzo / Castiglion Fiorentino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

1 / 8

Province of Arezzo / Castiglion Fiorentino

14 39 Min stay varies

  • 14 bedrooms
  • Sleeps 39
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £65 / night

£428 / week

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from £65 / night

(4) Excellent 

1 / 18

Province of Arezzo / Castiglion Fiorentino

5 12 7 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £110 / night

£770 - £1069 / week

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from £110 / night

(3) Excellent 

1 / 18

Tuscany Holiday House - Castiglion Fiorentino apartment sleeps 6

Province of Arezzo / Castiglion Fiorentino

2 6 2 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Child friendly ; Car not necessary; Pet friendly;
Apartment with 2 bedrooms, 2 bathrooms, living room / kitchen, balcony, private entrance, internet free wi-fi h24. Completely renovated in 2008 respecting the characteristics of the classic Tuscan homes. Partly furnished with antiques expertly blended with modern conven  …see more

from £52 / night

£317 - £342 / week

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from £52 / night

1 / 7

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £60 / night

£385 / week

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from £60 / night

(7) Very Good 

1 / 18

Luxury villa with private swimming pool - Castiglion Fiorentino villa sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
The ideal destination for combining relax with culture. The unique location of the villa, the accuracy of design and all the comforts inside allow guests to fully enjoy the tuscan countryside by a unique view on it. Furthermore, the villa is situated in a strategic poin  …see more

from £171 / night

£1197 - £2308 / week

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from £171 / night

(2) Excellent 

1 / 18

Province of Arezzo / Castiglion Fiorentino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
 …see more

Pricing unknown

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Pricing unknown

1 / 12

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £69 / night

£300 / week

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from £69 / night

(4) Excellent 

1 / 23

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Car advised; Pet friendly;
 …see more

from £60 / night

£342 - £428 / week

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from £60 / night

1 / 8

Province of Arezzo / Castiglion Fiorentino

13 28 Min stay varies

  • 13 bedrooms
  • Sleeps 28
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £48 / night

£300 - £556 / week

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from £48 / night

1 / 24

Cortona Manor with sauna,in- and outdoor pool - Montecchio Vesponi villa sleeps 18

Castiglion Fiorentino / Montecchio Vesponi

9 18 7 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Located half way between Arezzo and Cortona,stands the villa enclosed in its fenced and gated garden. The private swimming pool (12x6m) lies immersed in scented flower-beds and fragrant herbs. A glass veranda frames the elegant manor house and allows to have outdoor mea  …see more

from £794 / night

£5556 - £6753 / week

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from £794 / night

1 / 20

San Lazzo, graceful apt in a special tuscan hamlet - Castiglion Fiorentino apartment sleeps 3

Province of Arezzo / Castiglion Fiorentino

2 3 3 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min stay
Key info: Ask owner if suitable for children; Ask about pets;
The picturesque Via San Lazzo, named after the characteristic small Romanesque church, winds along the massive Medieval walls surrounding the Etruscan town of Castiglion Fiorentino, once entered Porta Romana. Casa San Lazzo rises at the middle of the alley characterised  …see more

from £103 / night

£385 - £513 / week

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from £103 / night

1 / 18

Province of Arezzo / Castiglion Fiorentino

3 2 1 night min stay

  • 3 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Not suitable for children; Car advised;
 …see more

from £69 / night

£449 / week

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from £69 / night

(1) Excellent 

1 / 8

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £51 / night

£353 - £659 / week

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from £51 / night

Top Destination reviews

Luxury villa with private swimming pool
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 make sure the … 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
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

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