Villas in Castiglion Fiorentino: Rent luxury villas in Castiglion Fiorentino

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78 Holiday homes

Filters applied: Villa (78)

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

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 £259 / night

£1294 - £2587 / week

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from £259 / night

(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 £190 / night

£1330 / week

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from £190 / night

25

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 £585 / night

£4095 - £6811 / week

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from £585 / night

(1) Excellent 

22

Castiglion F. AR - ITA640 - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
This beautiful Tuscan holiday home is situated near Castiglion Fiorentino (AR). The villa has 3 double beds, so it can comfortably host a family or group of 6 people. There are also 4 bathrooms for individual comfort and privacy. Guests can relax and enjoy the tranquil  …see more

from £83 / night

£578 - £1336 / week

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from £83 / 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

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 £259 / night

£1725 - £2845 / week

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from £259 / 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 £278 / night

£1940 / week

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from £278 / 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 £1010 / night

£7069 / week

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from £1010 / night

100

Celeste - Brolio villa sleeps 18

Castiglion Fiorentino / Brolio

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
ExteriorVilla Celeste is a large villa with 9 bedrooms, all with en suite bathrooms.The property is in a perfect position for exploring wider Tucany with Arezzo and Cortona just a short distance away and other famed historical and arti  …see more

from £802 / night

£4095 - £6337 / week

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from £802 / 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 £173 / night

£1207 - £2328 / week

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from £173 / 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 £180 / night

£1254 - £1312 / week

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from £180 / 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 £328 / night

£1250 - £2742 / week

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from £328 / night

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
  • 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 £172 / night

£1207 - £2069 / week

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from £172 / 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 £216 / night

£1207 - £2414 / week

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from £216 / 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 £177 / night

£1233 - £2837 / week

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from £177 / 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 £179 / night

£1250 - £2399 / week

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from £179 / 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 £801 / night

£5604 - £7673 / week

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from £801 / night

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 £305 / night

£2130 / week

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from £305 / 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 £104 / night

£647 - £1207 / week

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from £104 / 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 £69 / night

£302 / week

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from £69 / night

28

Villa Castle - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
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 £414 / night

£2845 / week

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from £414 / night

(1) Poor 

100

Belladonna - Castiglion Fiorentino villa sleeps 11

Province of Arezzo / Castiglion Fiorentino

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
ExteriorsThis spacious house is in Castiglion Fiorentino, which is situated on a hill in the Valdichiana area. Its location guarantees a tranquil and relaxing stay, but not too far from the town center, which is only 3km away.There are many interesting places to visit i  …see more

from £141 / night

£987 - £1850 / week

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from £141 / 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 £165 / night

£1150 - £3219 / week

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from £165 / 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 £185 / night

£1294 - £2156 / week

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from £185 / 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

(3) Very Good 

23

Villa Margarita - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Castello Margarita is the ideal spot for those seeking relaxation and the convenience to explore Tuscany. Ideal for 4 - 16 guestsIt provides a compelling combination of a great location and charming farmhouse style. A recent renovation offering lots of space, light a  …see more

from £188 / night

£1311 / week

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from £188 / night

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 £616 / night

£4311 - £5518 / week

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from £616 / night

24

Luxury Tuscan Villa with Style and Space - Castiglion Fiorentino villa sleeps 12

Province of Arezzo / Castiglion Fiorentino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 23 km
  • Swimming pool
  • Suitable for children age 5+
his exceptional, luxurious and impeccable private villa in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Timeless views of the charming Val di Chio and beynd can be enjoyed from the terraces of the villa and the villa's poolsid  …see more

from £465 / night

£3250 / week

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from £465 / night

31

Province of Arezzo / Castiglion Fiorentino

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £370 / night

£2587 / week

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from £370 / night

25

La Casa di Pino Castiglion Fiorentino - Castiglion Fiorentino villa sleeps 2

Province of Arezzo / Castiglion Fiorentino

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
In the heart of the Val di Chio, on the border between Tuscany and Umbria and only a few km far form the village of Castiglion Fiorentino, we find the lovely CASA DI PINO, small and ancient stone cottage dated back to the year 1200, like the beautiful "Maestà" a painte  …see more

from £89 / night

£621 - £1009 / week

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from £89 / night

24

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

Castiglion Fiorentino / Montecchio Vesponi

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • 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 £801 / night

£5604 - £6811 / week

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from £801 / night

38

VILLA PRINCIPE 8 prsns - 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
  • 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 £104 / night

£647 - £2242 / week

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from £104 / night

26

Casa Largnano Palazzo del Pero - Castiglion Fiorentino villa sleeps 6

Province of Arezzo / Castiglion Fiorentino

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
A traditional stone farmhouse which emerges from the dense vegetation of the hills of Val Cerfone, a real oasis of peace immersed in nature, far from the noise and frenetic pace of modern day life. This house, which is in a natural park, is the ideal place for those wis  …see more

from £87 / night

£604 - £742 / week

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from £87 / night

20

95464001 - Castiglion Fiorenti - Pieve di Chio villa sleeps 8

Castiglion Fiorentino / Pieve di Chio

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
HOLIDAY HOME WITH SWIMMING POOL - VILLA CASSIANO Spacious holiday home with private swimming pool located just 8km away from Castiglion Fiorentino. The property is perfectly located between the beautiful towns of Arezzo and Cortona. This is the ideal place to spend a r  …see more

from £144 / night

£874 - £3060 / week

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from £144 / night

20

95463001 - Castiglion Fiorenti - Pieve di Chio villa sleeps 8

Castiglion Fiorentino / Pieve di Chio

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful villa with private pool is situated in Tuscany, a short distance away the town of Castiglion Fiorentino, between the historical cities of Cortona and Arezzo. This rental is an ideal destination for those seeking for tranquillity. A large garden with a pr  …see more

from £207 / night

£1311 - £3060 / week

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from £207 / 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 £104 / night

£647 - £1207 / week

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from £104 / 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 £173 / night

£1035 - £2242 / week

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from £173 / night

(2) Excellent 

79

Province of Arezzo / Castiglion Fiorentino

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £197 / night

£1375 - £1940 / week

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from £197 / night

17

Province of Arezzo / Castiglion Fiorentino

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Suitable for children age 5+

 …see more

from £179 / night

£1250 - £2399 / week

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from £179 / night

(3) Very Good 

65

Province of Arezzo / Castiglion Fiorentino

2 4 4 nights min

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

 …see more

from £255 / night

£1113 / week

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from £255 / 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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