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46 Results  |  

from £161 / night

£1127 - £2283 / week

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Excellent 5/5 

24 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

4 Nights min stay

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from £161 / night

£1127 - £2283 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Magical Villa with private pool on top of Tuscany Hills. One hour drive to Florence, Siena, Perugia. Near to Cortona, Montepulciano and Arezzo.  …see more

from £145 / night

£1015 - £1957 / week

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Excellent 5/5 

18 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

1 night min stay

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from £145 / night

£1015 - £1957 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Magnificent villa with swimming pool between Arezzo and Cortona  …see more

from £300 / night

£2095 - £3055 / week

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Excellent 5/5 

12 Photos

House / 6 Bedrooms / sleeps 13

Excellent 5/5 

7 Nights min stay

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from £300 / night

£2095 - £3055 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Il Ceriolo is a restored 18th century Tuscan farm house set on about five acres of land. The house includes six bedrooms and five baths, with a sleeping capacity of 13. A lovely pool is included. The pool is quite large and very private. An outdoor barbeque is available, along with alfresco dining.  …see more

Featured properties

from £151 / night

£1051 - £2305 / week

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Excellent 5/5 

22 Photos

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £151 / night

£1051 - £2305 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Inside the Villa Various paintings of flowers and colours of Tuscany hang on the walls bringing nature indoors. The living room is plain and simple, starting with the stone walls where the fireplace stands. Here you can take a relaxing break while watching satellite T  …see more

from £44 / night

£305 - £381 / week

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Excellent 5/5 

24 Photos

Farmhouse / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

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from £44 / night

£305 - £381 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Ideal to relax your body and your mind: beatiful landscape and trekking area; ideal place to visit all the central Italy: Arezzo, Cortona, Siena, Perugia, Assisi, La Verna, Camaldoli, Florence and also Rome.  …see more

from £39 / night

£269 - £290 / week

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Excellent 5/5 

18 Photos

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

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from £39 / night

£269 - £290 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Tuscany Holiday House Castiglion Fiorentino Historical City Center Check-in 3.00 pm - 8.00 pm Check-out before/entro 11.00 am  …see more

from £117 / night

£819 - £1486 / week

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37 Photos

Farmhouse / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £117 / night

£819 - £1486 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Old 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.  …see more

from £83 / night

£580 - £1486 / week

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21 Photos

House / 4 Bedrooms / sleeps 11

6 Nights min stay

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from £83 / night

£580 - £1486 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Strategic location to visit TUSCANY. Full packages available with tours (wine, food, historical, religious and many others).  …see more

from £125 / night

£869 - £1790 / week

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14 Photos

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £125 / night

£869 - £1790 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Holiday property located in Tuscany in Castiglion Fiorentino. Close location to many touristic attractions like Cortona, Arezzo, Siena, Montepulciano, Montalcino, Chianti, Florence and many more makes it a fantastic place for family holidays.  …see more

from £163 / night

£1138 - £2022 / week

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21 Photos

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £163 / night

£1138 - £2022 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Villa with swimming pool near Cortona, with stunning view over the olive groves and the town of Castiglion Fiorentino  …see more

from £363 / night

£2537 - £5073 / week

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24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £363 / night

£2537 - £5073 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury villa with swimming pool, indoor pool and sauna near Cortona – sleeps 18+6 From 3500€ to 7000€ a week Possibility to add 6 extra beds  …see more

from £156 / night

£1087 - £1566 / week

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24 Photos

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £156 / night

£1087 - £1566 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
In the Cortona countryside, 2 km from Castiglion Fiorentino. private garden wiht large pool.  …see more

from £138 / night

£966 - £2706 / week

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8 Photos

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £138 / night

£966 - £2706 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on the border between Tuscany and Umbria, this lovely country villa has been recently built in perfect harmony with the surrounding territory.  …see more

from £143 / night

£1000 / week

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18 Photos

Farmhouse / 4 Bedrooms / sleeps 10

7 Nights min stay

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from £143 / night

£1000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
An ideal choice for those who love nature and art, in an authentic and elegant environment. Highly recommended for families with children. The feature of the farm is quiet and respect for the environment  …see more

from £91 / night

£631 - £935 / week

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36 Photos

Apartment / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £91 / night

£631 - £935 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • 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,  …see more

from £82 / night

£573 - £1000 / week

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22 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £82 / night

£573 - £1000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The area around Castiglion Fiorentino includes all the characteristics of the typical Tuscan landscapes.  …see more

from £103 / night

£718 - £1370 / week

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33 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £103 / night

£718 - £1370 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Ancient 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.  …see more

from £74 / night

£515 - £827 / week

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38 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £74 / night

£515 - £827 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Casa Pantoufle is an old, stone farmhouse surrounded by silver olive trees in a panoramic, hill position at about 800 m above sea level and overlooking the Castle of Montecchio and the whole Valdichiana Valley.  …see more

Pricing unknown

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Apartment / 1 Bedroom / sleeps 2

Min stay varies

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Pricing unknown

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Key info:

  • Great for children of all ages
  • Pets welcome
This cozy apartment is located in the beautiful setting of the Tuscan hills, in the center of the medioeval village of Castiglion Fiorentino. Few minutes away from Cortona, close to Pienza, Montepulciano, Siena, Florence, Pisa.. the perfect location to explore Tuscany!  …see more

from £197 / night

£1377 - £2573 / week

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Excellent 5/5 

23 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

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from £197 / night

£1377 - £2573 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Good value Tuscan Home for families or friends, Private pool, beautiful views, lots of space both inside and out. Additional facilities can be provided - A chef to prepare a lovely lunch or dinner for that special occasion, a concierge serve with local insight,  …see more

from £94 / night

£653 - £1377 / week

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Very Good 4.5/5 

23 Photos

Villa / 4 Bedrooms / sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £94 / night

£653 - £1377 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Castello Margarita is the ideal spot for those seeking relaxation and the convenience to explore Tuscany. Ideal for 4 - 16 guests It provides a compelling combination of a great location and charming farmhouse style.  …see more

from £156 / night

£1087 - £2609 / week

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Excellent 5/5 

24 Photos

Villa / 4 Bedrooms / sleeps 11

Excellent 5/5 

3 Nights min stay

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from £156 / night

£1087 - £2609 / week

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Key info:

  • Nearest beach 128 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Opened in 2010 .Beautiful villa in panoramic position with private pool in the countryside 8/11persons.Peaceful e charming location, ideal for families or groups. 4 bedroom / 6 bathroom. Only 10km from Cortona , 10 min from the village of Castiglion Fiorentino.  …see more

from £59 / night

£410 - £609 / week

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Very Good 4.5/5 

24 Photos

Villa / 1 Bedroom / sleeps 2

Very Good 4.5/5 

7 Nights min stay

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from £59 / night

£410 - £609 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
San Regolo in Brolio is a lovely brand new hamlet with a small collection of villas located on the edge of the village of San Regolo, and is within easy walking distance of the centre of the village.  …see more

from £456 / night

£3189 - £5073 / week

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24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £456 / night

£3189 - £5073 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Villa Celeste is a grand villa accommodating up to 18 and ideal for a large group or family holiday combining culture and relaxation. It boasts lovely décor, privacy and excellent facilities including both an outdoor and indoor pool.  …see more

from £141 / night

£986 - £1754 / week

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Very Good 4.5/5 

13 Photos

Villa / 5 Bedrooms / sleeps 10

Very Good 4.5/5 

7 Nights min stay

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from £141 / night

£986 - £1754 / week

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Key info:

  • Nearest beach 27 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
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.  …see more

from £278 / night

£1945 / week

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19 Photos

Villa / 4 Bedrooms / sleeps 10

7 Nights min stay

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from £278 / night

£1945 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Chio is nestled in the Tuscan hillside covered by an olive grove at 350 meters above sea level in a panoramic position showcasing the town of Castiglion Fiorentino.  …see more

from £236 / night

£1649 - £2138 / week

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18 Photos

House / 5 Bedrooms / sleeps 11

7 Nights min stay

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from £236 / night

£1649 - £2138 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Magnificent villa in a beautiful hillside position with breathtaking views, close to the medieval walled village of Castiglion Fiorentino.  …see more

from £194 / night

£1355 - £2328 / week

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24 Photos

Farmhouse / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £194 / night

£1355 - £2328 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Castiglion Fiorentino with 4 bedrooms sleeps 8  …see more

from £182 / night

£1272 - £2348 / week

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9 Photos

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £182 / night

£1272 - £2348 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Casale Fiorentinaandnbsp;is a beautiful stone farmhouse located inandnbsp;Castiglion Florentinoandnbsp;amidst the Tuscan country side with its olive groves and rich vineyards.andnbsp; Theandnbsp;kitchenandnbsp;opens onto the outside dining area, a covered porch  …see more

from £142 / night

£989 - £1730 / week

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24 Photos

Farmhouse / 6 Bedrooms / sleeps 13

7 Nights min stay

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from £142 / night

£989 - £1730 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Castiglion Fiorentino with 6 bedrooms sleeps 13  …see more

from £363 / night

£2537 - £5073 / week

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24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £363 / night

£2537 - £5073 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Magnifica is an old country residence, skilfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property.  …see more

from £215 / night

£1500 - £3100 / week

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17 Photos

Villa / 4 Bedrooms / sleeps 12

4 Nights min stay

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from £215 / night

£1500 - £3100 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa la Rustica is a private villa situated 550 meters above sea level and nestled in an isolated Tuscan hillside surrounded by olive groves and oak trees. It is located 8 km from the town of Castiglion Fiorentino and a step away from Cortona and Umbria.  …see more

from £149 / night

£1037 - £1508 / week

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23 Photos

Villa / 2 Bedrooms / sleeps 6

3 Nights min stay

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from £149 / night

£1037 - £1508 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Holiday villa rentals in Castiglion Fiorentino, just 18 kms away from Arezzo, Italy.andnbsp; The villa is situated in the beautiful Tuscan countryside just 18 Km from Arezzo, 15 Km from Cortona and 60 Km from Siena. A convent of the XIII century recently restored is sit  …see more

from £96 / night

£671 - £906 / week

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16 Photos

Cottage / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £96 / night

£671 - £906 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
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 your family vacation.  …see more

from £263 / night

£1840 - £3664 / week

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24 Photos

Farmhouse / 9 Bedrooms / sleeps 22

3 Nights min stay

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from £263 / night

£1840 - £3664 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Marciano Della Chiana with 9 bedrooms sleeps 22  …see more

from £202 / night

£1409 - £2348 / week

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20 Photos

Villa / 7 Bedrooms / sleeps 14

Min stay varies

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from £202 / night

£1409 - £2348 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Romanaandnbsp;is sited in the middle of an uninhabited medieval village enjoying the privacy and serenity of nature and old time places.andnbsp; Welcoming up toandnbsp;14 people,andnbsp;the villa is comfortably furnished with period furniture and medieval  …see more

from £363 / night

£2537 - £6595 / week

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18 Photos

Villa / 9 Bedrooms / sleeps 18

Min stay varies

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from £363 / night

£2537 - £6595 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Welcome to the Tuscany wedding villa Michele in Arezzo, Italy that has the capacity ofandnbsp;18 peopleandnbsp;with babysitter and andnbsp;indoor pool facilities. andnbsp;The Tuscan Villa Michele is an old country residence specially remodeled into an exclusive  …see more

from £116 / night

£807 - £1697 / week

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18 Photos

House / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £116 / night

£807 - £1697 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This is a typical, renovated, ancient manor house, tastefully furnished and surrounded by olive and cypress trees. The stone oven, the washboard on the grass and the ancient mangers has been kept. The comfortable living room on the ground floor has typical small wind...  …see more

from £83 / night

£577 - £1206 / week

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24 Photos

House / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £83 / night

£577 - £1206 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This attractive holiday property, located within the grounds of the owners' home, has been tastefully decorated and furnished to a good standard. The house is in a private property and has a private garden and terraces with furniture, perfect for dining al fresco. Th...  …see more

from £240 / night

£1677 - £3096 / week

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24 Photos

House / 6 Bedrooms / sleeps 13

7 Nights min stay

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from £240 / night

£1677 - £3096 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This magnificent stone house is spacious and set in a superb location, with uninterrupted views of the Chiana valley. Here you can enjoy the peace and quiet of your surroundings. The living space extends over three floors, with several entrances from the outside. The...  …see more

from £163 / night

£1138 - £2167 / week

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26 Photos

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £163 / night

£1138 - £2167 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
In the shadows of Castiglion Fiorentino, This impeccable and charming villa is perfect for touring Cortona, Pienza, Montepulciano and many of the Tuscan hill towns. It is perfect for family reunions, a vacation for friends - but always, something special to enjoy  …see more

from £208 / night

£1450 / week

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16 Photos

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £208 / night

£1450 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Family friendly villa  …see more

from £725 / night

£5073 / week

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11 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £725 / night

£5073 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Family friendly villa Luxury villas Villas in Tuscany for groups  …see more

from £311 / night

£2174 / week

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20 Photos

Manor House / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £311 / night

£2174 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Family friendly villa Luxury villas Villas in Tuscany for groups  …see more

from £356 / night

£2487 / week

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12 Photos

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £356 / night

£2487 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Family friendly villa Villas in Tuscany for groups  …see more

from £130 / night

£906 / week

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18 Photos

Villa / 5 Bedrooms / sleeps 12

1 night min stay

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from £130 / night

£906 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
La casa è dotata di tutti i confort per una piacevole vacanza in tranquillità e relax. Piscina grande per rinfrescarsi nelle giornate estive e grande vasca idromassaggio riscaldata situata all'esterno con vista sulle colline di Castigion Fiorentino. Nel Giardino, dotat  …see more

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