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62 Holiday homes

Filters applied: Private garden (62)

(4) Excellent 

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

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 £192 / night

£1341 / week

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from £192 / night

21

Villa with pool near Cortona - Castiglion Fiorentino villa sleeps 8

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 £261 / night

£1305 - £2609 / week

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from £261 / night

44

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

Province of Arezzo / Castiglion Fiorentino

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • 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 £131 / night

£957 - £1174 / week

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from £131 / night

(5) Excellent 

19

Casa Dei Sogni, Tuscan Villa, Private Pool, A/C - Pieve di Chio villa sleeps 6

Castiglion Fiorentino / Pieve di Chio

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 25 km
  • Swimming pool
  • Child friendly
A place to feel at home in Tuscany.... Lovely air conditioned stone farmhouse situated within a small Tuscan borgo. The house offers high quality accommodation with outstanding views of the Val di Chio and Castiglion Fiorentino from the bedrooms, private pool and te  …see more

from £225 / night

£1680 - £2048 / week

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from £225 / night

(3) Very Good 

22

Tuscany cottage with Private Pool, BBQ, & Parking - Pieve di Chio cottage sleeps 6

Castiglion Fiorentino / Pieve di Chio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Charming Restored character stone cottage with beautiful views across the Val Di Chio. Private swimming pool with Stone BBQ. Ideal location for day trips across Tuscany & Umbria, Siena, Montepulciano, Cortona, Perugia & Assisi. 15 minutes to Medieval town with train S  …see more

from £124 / night

£864 - £1152 / week

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from £124 / night

(1) Excellent 

23

Capuchi Cottage - Orzale condo sleeps 2

Castiglion Fiorentino / Orzale

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • 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 £78 / night

£542 - £660 / week

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from £78 / night

(7) Very Good 

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
  • 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 £174 / night

£1218 - £2348 / week

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from £174 / night

(3) Excellent 

4

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

Province of Arezzo / Castiglion Fiorentino

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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 £181 / night

£1261 - £2420 / week

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from £181 / night

(5) Excellent 

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
  • 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 £218 / night

£1218 - £2435 / week

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from £218 / night

(12) Excellent 

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
  • 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 £331 / night

£1261 - £2766 / week

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from £331 / night

(9) Very Good 

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
  • 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 £83 / night

£650 - £727 / week

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from £83 / night

33

VILLA CECILIA Castiglion Fiorentino - Castiglion Fiorentino farmhouse sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
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 £123 / night

£861 - £1644 / week

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from £123 / night

(13) Excellent 

24

Borgo Tranquiitta - Il Sole - Castiglion Fiorentino cottage sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 £99 / night

£689 - £718 / week

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from £99 / night

13

Castiglion Fiorentino / Pieve di Chio

8 30 2 nights min

  • 8 bedrooms
  • Sleeps 30
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £70 / night

£470 - £609 / week

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from £70 / night

(9) Excellent 

27

Borgo Tranquiitta - Le Stella - Castiglion Fiorentino cottage sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 £101 / night

£704 - £734 / week

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from £101 / night

18

Villa degli Affreschi - Castiglion Fiorentino villa sleeps 18

Province of Arezzo / Castiglion Fiorentino

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa is located in the heart of Valdichiana, close to Arezzo and Cortona, the relais offers the possibility to reach easily the main historical and artistic sites such as Florence, Siena, Perugia, Montepulciano, Assisi, Gubbio and lots more. Villa degli  …see more

from £808 / night

£5653 - £7740 / week

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from £808 / night

(1) Excellent 

38

La Madonnina - Castiglion Fiorentino villa sleeps 9

Province of Arezzo / Castiglion Fiorentino

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 £178 / night

£1244 - £2861 / week

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from £178 / night

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
  • 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 £107 / night

£748 / week

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from £107 / night

16

Villa Rossi - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The property is located in Poggio Della Coppa near Castiglion Fiorentino at about 650 meters above sea level and is situated on a hillside with amazing views of the valley below. The 2-storey stone building is contructed in typical Tuscan farmhouse style with an extern  …see more

from £261 / night

£1740 - £2870 / week

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from £261 / night

36

LA PIETRAIA Castiglion Fiorentino Walking distance - Castiglion Fiorentino apartment sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
In a panoramic and quiet position, walking distance to the village of Castiglion Fiorentino, one of the most important villages in the Valdichiana with shops, restaurants and all kinds of facilities, we find a cottage divided into two pleasant apartments, each one with  …see more

from £109 / night

£757 - £1148 / week

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from £109 / night

(2) Excellent 

30

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

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • 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 £280 / night

£1957 / week

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from £280 / night

58

Villa Magnifica - Brolio villa sleeps 18

Castiglion Fiorentino / Brolio

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • 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 £591 / night

£4131 - £6870 / week

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from £591 / night

(2) Excellent 

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
  • 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 £187 / night

£1305 - £2174 / week

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from £187 / night

11

Coppa di Sopra - Castiglion Fiorentino villa sleeps 6

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. 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 £181 / night

£1265 - £1323 / week

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from £181 / night

(4) Excellent 

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
  • 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 £105 / night

£653 - £1218 / week

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from £105 / night

(1) Excellent 

37

CASALE IL TRECENTO Castiglion Fiorentino - Castiglion Fiorentino farmhouse sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
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 £141 / night

£983 - £1966 / week

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from £141 / night

(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 £52 / night

£360 - £670 / week

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from £52 / 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

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Pricing unknown

23

Province of Arezzo / Castiglion Fiorentino

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

14

Villa Sant Antonio - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 £307 / night

£2148 / week

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from £307 / night

(1) Very Good 

21

Casa Matilde, Private Pool Cosy Tuscan Family Home - Castiglion Fiorentino cottage sleeps 4

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
Casa Matilde. Family Home for 3-4 guests. Private Pool. Cottage Matilde is an independent cottage within a small hamlet. It offers a private pool and some lovely views of the surrounding countryside. With two bedrooms, sitting room and kitchen, it offers a great opport  …see more

from £87 / night

£605 / week

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from £87 / night

40

Castello di Ginevra - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Private garden
<br>Castello di Ginevra – Castel Fiorentino – Tuscany<br><br>6 Bedrooms - Pool<br><br>Nestling in the heart of the world-famous Chianti Valley, just thirty minutes from Florence, stands Castello  di Ginevra. This graceful country r  …see more

from £1019 / night

£7131 / week

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from £1019 / night

7

Province of Arezzo / Castiglion Fiorentino

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

Pricing unknown

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Pricing unknown

15

Villa Manciano - La Nuova Torretta - Castiglion Fiorentino barn sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • 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 £157 / night

£1087 / week

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from £157 / night

(6) Excellent 

12

Villa Il Ceriolo - Castiglion Fiorentino house sleeps 13

Province of Arezzo / Castiglion Fiorentino

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 £435 / night

£3044 / week

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from £435 / night

(2) Excellent 

18

Province of Arezzo / Castiglion Fiorentino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

43

Villa Colline Senesi - Brolio villa sleeps 18

Castiglion Fiorentino / Brolio

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Private garden
<br>Villa Colline Senesi - Val di Chiana – Tuscany9 Bedrooms – Indoor / Outdoor Pool<br><br>Villa Colline Senesi is an old country residence, skilfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style g  …see more

from £622 / night

£4348 - £5566 / week

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from £622 / night

14

Cottage Grande, Lovely Home - Pieve di Chio house sleeps 6

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 place to feel at home in Tuscany. 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  …see more

from £123 / night

£857 - £878 / week

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from £123 / night

17

LA MONTANINA Castiglion Fiorentino - Castiglion Fiorentino farmhouse sleeps 4

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
A few kilometres from Castiglion Fiorentino and Cortona, on the way up the slopes of the Montanina hill, at the top of which the ruins of an ancient castle can be seen through the vegetation, this typical farmhouse has recently been renovated while still maintaining its  …see more

from £64 / night

£444 - £1000 / week

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from £64 / night

8

Villa Giovanna - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
Situated on the border between Tuscany and Umbria, this lovely country villa has been recently built in perfect harmony with the surrounding territory. A welcoming property with all modern comforts, it is the perfect choice for anyone looking for a traditional feel wit  …see more

from £166 / night

£1160 - £3247 / week

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from £166 / night

Top Destination reviews

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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