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48 Results  |  
18 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £162 /night

£1130 - £2178 / 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

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £172 /night

£1202 - £2500 / 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £42 /night

£294 - £424 / 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

Featured properties

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

18 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £93 /night

£646 - £726 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Italia, Toscana, casa vacanza, Cortona, Castiglion Fiorentino, Arezzo, etruschi, natura e libertà. A due passi dal lago Trasimeno  …see more

8 Photos

Guest house | 14 Bedrooms | sleeps 39

Excellent 5/5 

2 Nights min stay

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from £47 /night

£323 - £404 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Gli appartamenti e gli spazi comuni sono stati ristrutturati con classe ed eleganza, offrendo alloggi di lusso e un servizio di alto livello.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £127 /night

£887 - £2000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The structure, typical of Tuscany, is located on an extremely scenic natural plateau near Castiglion Fiorentino between the towns of Cortona and Arezzo.Pool. Jacuzzi. Four bedrooms. Three bathrooms.  …see more

23 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £115 /night

£799 - £1202 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
ENCHAINTING VILLA with private POOL on top of TUSCAN HILLS. 10 minutes drive to the town of Castiglion Fiorentino. 25 to CORTONA. One hour to FIRENZE, PERUGIA and SIENA. 30 minutes to the TRASIMENO LAKE.  …see more

17 Photos

Barn | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £121 /night

£847 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Manciano is the ideal place to stay in Tuscany, for relax and also for daily drives into the best places of Tuscany and Umbria  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £404 /night

£2823 - £5646 / 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

16 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £29 /night

£202 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
Bicamere in palazzo antico nel centro storico di caratteristico borgo toscano. Apartment in the historic centre of Castiglion Fiorentino, a typical Tuscan hill-top town, in a region's uniquely rich for cultural and artistic heritage (Tuscany and nearby Umbria)  …see more

7 Photos

Townhouse | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £35 /night

£242 - £363 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Grazioso e comodo appartamento con giardino e garage, a Castiglion Fiorentino (Toscana). 2 camere da letto, max 5 ospiti. Per un tranquillo periodo di vacanza. A 10 Km da Cortona, 15 Km da Arezzo, 50 Km da Perugia, 60 Km da Siena, 90 Km da Firenze.  …see more

15 Photos

Cottage | 4 Bedrooms | sleeps 15

2 Nights min stay

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from £127 /night

£888 - £1775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
Spinabbio è il luogo ideale per passare al meglio le vostre vacanze tra relax e cultura.Potrete visitare la vicinissima Cortona,Arezzo,Siena e Perugia.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £219 /night

£1533 - £2863 / 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

20 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

4 Nights min stay

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from £132 /night

£924 - £2654 / 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
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.  …see more

23 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £168 /night

£1170 - £2218 / 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

13 Photos

Villa | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

7 Nights min stay

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from £157 /night

£1097 - £1952 / 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

24 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £78 /night

£542 - £642 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Extra guests? There is also a separate studio available which has additional bed and bathroom should you require additional space. The proeprty is great for half term school holidays as well as the longer summer family holidays in Tuscany.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 16

Very Good 4/5 

7 Nights min stay

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from £144 /night

£1008 - £2162 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This rustic Castiglion country house for 16 people, with 7 bedrooms and 3 bathrooms, is ideal for large families. Located in the popular region of Tuscany in Italy, this house offers a beautiful private swimming pool.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £78 /night

£542 - £642 / week

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Key info:

  • Nearest beach 27 km
  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
There is also a separate studio with additional bed and bathroom if you need more space . Great value family holiday homes in Tuscany, Large pool and amazing views. Perfectly to tour Tuscany and Umbria including the towns of Cortona, Pienza, Arezzo, Assisi, Siena etc  …see more

23 Photos

Condo | 1 Bedroom | sleeps 2

Excellent 5/5 

7 Nights min stay

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from £70 /night

£488 - £600 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
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. Private and cosy, perfect for a quiet romantic time in Tuscany  …see more

24 Photos

Cottage | 3 Bedrooms | sleeps 5

Very Good 4.5/5 

Short stays welcome

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from £78 /night

£542 - £714 / week

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Key info:

  • Nearest beach 26 km
  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Late availability, Good value Family Holiday Tuscany, Perfect for half term holidays as well as extended summer vacations in Tuscany. One of three, lovely detached cottages lovingly restored with large pool and gardens. Large pizza oven, private terraces and pergolas.  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £660 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Sandia C is a cozy and welcoming apartment. It sleeps three people. From Villa Sandia C you will have a nice view of the garden. Villa Sandia C is 35 square meters (375 square feet)  …see more

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

16 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £108 /night

£755 / 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

24 Photos

Farmhouse | 6 Bedrooms | sleeps 13

7 Nights min stay

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from £158 /night

£1100 - £1925 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £97 /night

£678 - £847 / week

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Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
These apartments located on the ground or first floor offer sitting room, 1 or 2 doubel bedrooms, bathrooms with shower. There is a hall for events, a swimming pool and parking area.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £173 /night

£1209 - £2517 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This lovely accommodation set in Tuscany, Italy, has 4 bedrooms and 4 bathrooms, and is perfect for those who are looking for a unique experience. This property comes with a swimming pool.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £116 /night

£811 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Classic stone cottage in the vicinity of Castiglion Fiorentino and Cortona in Tuscany.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £404 /night

£2823 - £5646 / 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

18 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £69 /night

£480 - £601 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
The freshness of this charming garden apartment offering space and easy access to many of Tuscany's hill towns, vineyards and festivals., makes it a good choice for families (or friends) looking for something special and a lovely home in Tuscany  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £216 /night

£1508 - £2591 / 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

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £65 /night

£452 - £621 / week

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Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
These apartments located on the ground or first floor offer sitting room, 1 or 2 doubel bedrooms, bathrooms with shower. There is a hall for events, a swimming pool and parking area.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £235 /night

£1645 - £3064 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
elegant villa, located in Tuscany Italy, has a max. capacity of 12 people. This elegant villa is ideal for families and friends  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £78 /night

£541 - £1170 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This lovely accommodation set in Tuscany, Italy, has 3 bedrooms and 4 bathrooms, and it is perfect for those who are looking for peace and quiet. This pet-friendly property comes with a swimming pool and an Internet connection.  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

4 Nights min stay

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from £55 /night

£380 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
An lovely independent apartment - once the old bakery of the town. Nestled in the historic center of Castiglion Fiorentino with lovely views of the ancient buildings, the famous valleys "Val di Chio and Val di Chiana" and some of the surrounding hill towns.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £139 /night

£970 - £1250 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Belide A is a graceful attic. It sleeps four people. From Casa Belide A you will have a pleasant view of the greenery and of the surrounding countryside. Casa Belide A is 55 square meters (590 square feet)  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £660 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Sandia A is a characteristic and welcoming apartment. It sleeps three people. From Villa Sandia A you will enjoy a pleasant view of the garden. Villa Sandia A is 40 square meters (430 square feet)  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £660 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Sandia D is a welcoming apartment. It sleeps three people. From Villa Sandia D you will have a pleasant view of the garden. Villa Sandia D is 30 square meters (320 square feet)  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £115 /night

£800 - £1320 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Sandia B is a pleasant and spacious two-story apartment. It sleeps four people. From Villa Sandia B you will enjoy a pleasant view of the garden. Villa Sandia B is 60 square meters (645 square feet)  …see more

24 Photos

Farmhouse | 9 Bedrooms | sleeps 22

3 Nights min stay

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from £293 /night

£2048 - £4077 / 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

18 Photos

House | 5 Bedrooms | sleeps 11

7 Nights min stay

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from £263 /night

£1835 - £2380 / 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

16 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £231 /night

£1613 / 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

26 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £181 /night

£1267 - £2412 / 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

19 Photos

Villa | 4 Bedrooms | sleeps 10

Min stay varies

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from £180 /night

£1260 - £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

12 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £396 /night

£2768 / 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

20 Photos

Manor House | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £346 /night

£2420 / 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

11 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £807 /night

£5646 / 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

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