Horse riding holiday villas and apartments Castiglion Fiorentino | Holiday Lettings

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66 Holiday homes

Filters applied: Horse riding (66)

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

(2) Excellent 

1 / 30

Villa Castalini Tuscany, Incredible Views and more - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 25 km; Swimming pool; Child friendly ;
Perfect for Families and Friends, this spacious and comfortable Tuscan Villa provides more than just a place to stay... Providing absolute WOW views, this beautifully restored six bed-roomed and 5 bathroom Tuscan stone villa sleeps up to 12 guests. The villa offers pe  …see more

from £275 / night

£1924 / week

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from £275 / night

(2) Very Good 

1 / 16

Villa Maria - ALVINI Apartment - Castiglion Fiorentino apartment sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Tucked away in a quiet corner of Tuscany lies Villa Maria and Apartment Alvini, offering great value family holidays.The villa offers two lovely independent apartments which are perfect for family and friends offering a huge pool with water fall along with unspoilt vis  …see more

from £84 / night

£586 - £842 / week

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from £84 / night

Featured properties

1 / 18

Santa Lucia - Castiglion Fiorentino house sleeps 11

Province of Arezzo / Castiglion Fiorentino

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
The home is carefully decorated in a classic Tuscan style with well maintained outdoor areas.Its large lounge area with wonderful ancient brick arches, the swimming pool bordered by flowers and olive trees, and the elegant Tuscan décor create an enchanting setting for  …see more

from £278 / night

£1945 - £2522 / week

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from £278 / night

1 / 21

Madonnina Agriturismo - Castiglion Fiorentino apartment sleeps 5

Province of Arezzo / Castiglion Fiorentino

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
The Madonnina Agriturismo is very quiet, in a very sunny location with wonderful view over the Valdichiana valley. The ideal location for those who wish to spend a holiday in a quiet area. You can walk through the olive groves or relax poolside The stone house has two v  …see more

from £154 / night

£770 / week

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from £154 / night

(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

(13) Excellent 

1 / 24

Borgo Tranquiitta - Il Sole - Castiglion Fiorentino cottage sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 27 km; Swimming pool; Suitable for children age 5+;
The charming estate of Borgo Tranquiitta is surrounded by wooded hills of olives and bucolic charm that surround it like a natural garden enclosing the village in beautiful countryside with extended views of the valley and beyond.Here are three, lovely detached cottages  …see more

from £97 / night

£677 - £723 / week

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from £97 / night

(5) Excellent 

1 / 15

Villa Maria. Nonna, Tuscany - Castiglion Fiorentino apartment sleeps 5

Province of Arezzo / Castiglion Fiorentino

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 25 km; Swimming pool; Child friendly ;
Tucked away in a quiet corner of Tuscany lies Villa Maria offering great value family vacations.The villa offers two lovely independent apartments which are perfect for family and friends offering a huge pool with water fall and unspoilt vistas of the historic valley of  …see more

from £81 / night

£567 - £790 / week

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from £81 / night

(9) Excellent 

1 / 27

Borgo Tranquiitta - Le Stella - Castiglion Fiorentino cottage sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 25 km; Swimming pool; Suitable for children age 5+;
* Early Bird Saver * Via Holiday-lettings.. 8% saving for reservations made for summer 2016 made before january 30. (Mention this offer) The charming estate of Borgo Tranquiitta is surrounded by wooded hills of olives and bucolic charm that surround it like a natura  …see more

from £99 / night

£692 - £736 / week

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from £99 / night

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 / 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 - £736 / week

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from £106 / night

(4) Excellent 

1 / 13

Impressive stone built Tuscan holiday villa with private grounds and swimminig pool, sleeps 10 - Castiglion Fiorentino villa sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 27 km; Swimming pool; Child friendly ;
Just a short distance from the medieval town of Castiglion Fiorentino is "Casa Usignoli". This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms. The villa sits in one  …see more

from £189 / night

£1318 - £2118 / week

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from £189 / night

(9) Very Good 

1 / 24

Borgo Tranquiitta - La Luna - Castiglion Fiorentino cottage sleeps 5

Province of Arezzo / Castiglion Fiorentino

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 26 km; Swimming pool; Suitable for children age 5+;
Great Family holiday home. The charming estate of Borgo Tranquiitta is surrounded by wooded hills of olives and bucolic charm that surround it like a natural garden enclosing the village in beautiful countryside with extended views of the valley and beyond.Here are thre  …see more

from £82 / night

£639 - £749 / week

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from £82 / 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

(6) Excellent 

1 / 12

Villa Il Ceriolo - Castiglion Fiorentino house sleeps 13

Province of Arezzo / Castiglion Fiorentino

6 13 7 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
The beautiful old stone house is quite large, incorporating 4,500 sf (400 sm). It includes a total of six bedrooms and five baths, with a sleeping capacity of 13. The property includes a lovely garden with a small vineyard and numerous olive trees.Il Ceriolo is locate  …see more

from £428 / night

£2992 / week

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from £428 / night

1 / 98

Beautiful Home in Tuscany, Stunnng Private Pool - Pieve di Chio villa sleeps 6

Castiglion Fiorentino / Pieve di Chio

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; Pet friendly;
The view from here is - "just stunning but wait until you see the pool..." Villa Castello Roccolo - is - "simply beautiful " Villa Castello Roccolo is for sure, a really special property for both friends and families to enjoy. Tucked away on the sleepy hillside of  …see more

from £171 / night

£1197 - £2052 / week

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from £171 / night

1 / 14

Villa Sant Antonio - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Child friendly ; Ask about pets; Private garden;
Villa Sant Antonio is a beautiful holiday property in the heart of Tuscany, in Castiglion Fiorentino, close to Cortona and Arezzo. Great location in the middle of the olive growth, recently restored and beautifully furnished, full of art and antiques, with private swimm  …see more

from £302 / night

£2112 / week

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from £302 / night

1 / 25

Villa Magnifica - Brolio villa sleeps 18

Castiglion Fiorentino / Brolio

9 18 7 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Nearest beach 125 km; Swimming pool; Child friendly ;
Villa Magnifica is an old country residence, skillfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property. Large external pool with roman staircase and the bonus of the heated in  …see more

from £580 / night

£4060 - £6753 / week

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from £580 / night

(1) Excellent 

1 / 23

Capuchi Cottage - Orzale condo sleeps 2

Castiglion Fiorentino / Orzale

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
This romantic garden cottage, sits in the sleepy hamlet of Orzale and provides the perfect place to unwind and enjoy Tuscany. Simple, but charming accommodation - and a private pool. Capuchi cottage is immersed in the beautiful Tuscan country side. It provides an ine  …see more

from £77 / night

£533 - £649 / week

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from £77 / night

1 / 28

Villa Castle - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 12 1 night min stay

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay
Key info: Swimming pool; Ask owner if suitable for children; Car advised;
Immersed in the green of the olive trees and woods in the peaceful hills of Tuscany, the ideal destination for those seeking a healthy and peaceful stay of relaxation and comfort, Villa Il Castello is located between the cities of Arezzo and the quiet Etruscan town of C  …see more

from £411 / night

£2821 / week

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from £411 / night

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

(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 / 16

Villa Manciano, Il Fienile - Castiglion Fiorentino apartment sleeps 7

Province of Arezzo / Castiglion Fiorentino

2 7 3 nights min stay

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Pet friendly;
Villa Manciano is a very typical old stone Holiday House that was supposed to be also an elementary school about 100 years ago, for the kids of the rural Manciano area. The property is more than 3 acres (12.000 sq. meters) located in the strategical area of the Chiana V  …see more

from £116 / night

£812 / week

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from £116 / night

1 / 18

Villa Nonna, Garden Apartment - Castiglion Fiorentino house sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 23 km; Swimming pool; Child friendly ;
Fresh, bright and very well maintained, the villa offers a great holiday home for famiies of all ages. It is located in the lovely Val di Chio a few kilometers from the small town of ancient medieval town of Castiglion Fiorentino - rich in history, in the heart of b  …see more

from £85 / night

£590 - £671 / week

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from £85 / night

1 / 44

Farmhouse,private pool, hudge park,panoramic view - Castiglion Fiorentino farmhouse sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: 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 + 2 c  …see more

from £129 / night

£941 - £1283 / week

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from £129 / night

1 / 11

Coppa di Sopra - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 25 km; Child friendly ; Car essential;
Coppa di Sopra is an elegant and enchanting villa overlooking one of Tuscany's favorite valleys - “Coppa di Sopra is a magical place. It seems like you're on top of the world. We parked our car, walked down the steps and the view - it took our breath away!  …see more

from £167 / night

£1167 - £1300 / week

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from £167 / 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

(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

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

(4) Excellent 

1 / 48

Villa Bellavista, Tuscany 180 sqm - Castiglion Fiorentino villa sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Child friendly ;
San Martino is an ancient farm with three farm houses: for rent Villa Bellavista( 4 sleeps ), unique stone Villa with a relaxing atmosphere, lovingly restored and furnished.The Villa has own private pool 12mt x 5mt . The privacy is guaranted. The property consist of 9 e  …see more

from £103 / night

£642 - £1197 / week

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from £103 / 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 / 15

PODERE SPINABBIO - Castiglion Fiorentino cottage sleeps 10

Province of Arezzo / Castiglion Fiorentino

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Spinabbio è un antico casale ristrutturato secondo il suo originale stile rustico toscano, situato a 700 mt. S.l.m., immerso tra il verde di secolari boschi di querce e castagni, domina sullo splendido panorama della Val di Chiana. La particolare posizione consente il  …see more

from £184 / night

£1283 / week

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from £184 / night

1 / 33

VILLA CECILIA Castiglion Fiorentino - Castiglion Fiorentino farmhouse sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Property DescriptionAncient farmhouse of peasant origins, situated on the top a small hill in the heart of Valdichiana, at approx. 4 km from Castiglion Fiorentino, characteristic village with all kind of shop, restaurants and facilities. A recent and careful restoration  …see more

from £121 / night

£847 - £1616 / week

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from £121 / 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

(4) Excellent 

1 / 50

Villa Principe, Tuscany 210 sqm - Castiglion Fiorentino villa sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Child friendly ;
San Martino is an ancient farm of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio and Val di Chiana nearby the HISTORICAL TOWNS of Castiglion Fiorentino ( 10 min. ) and Cortona ( 20 min. ) Florence ( 1 hour ), Siena ( 1 hour ),  …see more

from £214 / night

£1197 - £2394 / week

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from £214 / night

(11) Excellent 

1 / 25

Villa Senaia - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Villa Senaia In stunning Tuscany, along its endless artistic heritage and countryside, where stretches of silvery olive trees stand after vineyards and cypress trees, lies the Villa Senaia. An ancient stone farmhouse, located in a strategic position where it is easy t  …see more

from £325 / night

£1240 - £2718 / week

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from £325 / night

(3) Excellent 

1 / 4

Villa Sophia in Brolio. Tuscany Family Home & Pool - Castiglion Fiorentino villa sleeps 9

Province of Arezzo / Castiglion Fiorentino

5 9 7 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
The sweeping vista across the valley to Cortona and Castiglion Fiorention with the wonderful castle of Montecchio makes the perfect base for a friends and family home in Tuscany. Recently renovated with great care and - attention to detail, Casa Sophia is a four bedro  …see more

from £178 / night

£1240 - £2378 / week

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from £178 / night

(1) Excellent 

1 / 38

La Madonnina - Castiglion Fiorentino villa sleeps 9

Province of Arezzo / Castiglion Fiorentino

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
The villa, of recent reconstruction, is positioned on the hills next to the characteristic town of Castiglion Fiorentino, in the middle of the Chiana valley and Chio valley amidst nature and art. Overlooking the wide expanse of the Val di Chiana, it offers a splendid vi  …see more

from £175 / night

£1223 - £2812 / week

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from £175 / night

(1) Excellent 

1 / 37

CASALE IL TRECENTO Castiglion Fiorentino - Castiglion Fiorentino farmhouse sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Property DescriptionOld farmhouse of peasant origins, where on the ground floor you can still appreciate the old stables. Located 1,5 km away from the town of Castiglion Fiorentino which can also be reached on foot. Castiglion Fiorentino is one of the most renowned town  …see more

from £138 / night

£966 - £1932 / week

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from £138 / 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

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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