Apartments and villas with a garden in Castiglion Fiorentino | Holiday Lettings UK

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111 Holiday homes

Filters applied: Garden (111)

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 £185 / night

£1294 - £3104 / week

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from £185 / night

(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

(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

Featured properties

(2) Excellent 

1 / 30

Villa Castalini Tuscany, Incredible Views and more

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

(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) 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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(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 £85 / night

£591 - £850 / week

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from £85 / 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

(4) Excellent 

1 / 19

Casa Dei Sogni, Tuscan Villa, Private Pool, A/C

Castiglion Fiorentino / Pieve di Chio

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: 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

(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

(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 £432 / night

£3018 / week

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from £432 / 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 / 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 £107 / night

£690 - £1768 / week

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from £107 / night

(2) Excellent 

1 / 22

Tuscany cottage with Private Pool, BBQ, & Parking

Castiglion Fiorentino / Pieve di Chio

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: 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 - £1296 / week

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from £124 / night

(1) Very Good 

1 / 21

Casa Matilde, Private Pool Cosy Tuscan Family Home

Province of Arezzo / Castiglion Fiorentino

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: 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 £86 / night

£600 / week

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from £86 / night

1 / 15

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

Province of Arezzo / Castiglion Fiorentino

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: 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 £156 / night

£1078 / week

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from £156 / night

1 / 12

Casa Del Cuore - with courtyard & Free wifi

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

£345 / week

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from £52 / 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 - £820 / week

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from £81 / night

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 £185 / night

£1294 / week

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from £185 / 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 £156 / night

£776 / week

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from £156 / 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 / 13

Impressive stone built Tuscan holiday villa with private grounds and swimminig pool, 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 - £2235 / week

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from £189 / 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 £117 / night

£819 / week

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from £117 / 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 £61 / night

£388 / week

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from £61 / 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 / 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 - £676 / week

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from £85 / night

(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

£432 / week

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from £65 / night

1 / 8

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 £31 / night

£259 / week

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from £31 / night

1 / 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
Key info: Swimming pool; Child friendly ; Car advised;
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

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 £585 / night

£4095 - £7673 / week

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from £585 / 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 £111 / night

£776 - £1656 / week

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from £111 / night

1 / 6

GELSOMINO - Castiglion Fiorentino apartment sleeps 6

Province of Arezzo / Castiglion Fiorentino

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
Gelsomino is a beautiful apartament entry on ground floor to a spacious sitting room with a large fireplace, and a well-equipped kitchen with a wood-burning stove; an internal stair leads to the upper floor with two rooms, each having a double bed plus optional single b  …see more

from £104 / night

£604 / week

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from £104 / 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

(3) Excellent 

1 / 4

Villa Sophia in Brolio. Tuscany Family Home & Pool

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 / 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

£302 / week

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from £69 / 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 £122 / night

£854 - £1630 / week

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from £122 / 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

£302 - £561 / week

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from £48 / 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 £104 / night

£647 - £1207 / week

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from £104 / 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 £305 / night

£2130 / week

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from £305 / night

1 / 18

Villa degli Affreschi - Castiglion Fiorentino villa sleeps 18

Province of Arezzo / Castiglion Fiorentino

9 18 7 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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

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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