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53 Results   |  
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 / 5 Bedrooms / sleeps 10

Excellent 5/5 

1 night min stay

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from £146 / night

£1022 - £1971 / 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

Farmhouse / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

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from £45 / night

£309 - £387 / 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

8 Photos

House / 2 Bedrooms / sleeps 5

Excellent 5/5 

2 Nights min stay

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from £48 / night

£331 - £567 / 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
Struttura piccola ma confortevole, capace di farvi passare le vostre vacanze in un luogo fantastico immerso nel verde, ma allo stesso tempo vicino alle principali città del centro della toscana. www.lamontanina.altervista.org  …see more

18 Photos

Villa / 3 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £85 / night

£589 / 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

22 Photos

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £153 / night

£1067 - £2339 / 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

24 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

3 Nights min stay

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from £164 / night

£1143 - £2317 / 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

22 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £83 / night

£581 - £1015 / 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

19 Photos

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £165 / night

£1153 - £2651 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden
The Villa has two stair. The large living room with sat TV and fireplace is on the ground floor, as is the fully equipped kitchen which gives onto the ample portico where one can dine overlooking the swimming pool and entire valley. There is also a double bedroom  …see more

21 Photos

House / 4 Bedrooms / sleeps 11

6 Nights min stay

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from £85 / night

£589 - £1508 / 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

33 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £104 / night

£728 - £1390 / 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

38 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £75 / night

£523 - £839 / 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

14 Photos

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £126 / night

£882 - £1817 / 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

37 Photos

Farmhouse / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £119 / night

£831 - £1508 / 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

24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £368 / night

£2574 - £5148 / 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 SPECIAL 10% SPRING DISCOUNT on full occupancy valid in April and May Possibility to add 6 extra beds  …see more

15 Photos

Barn / 3 Bedrooms / sleeps 6

3 Nights min stay

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from £120 / night

£840 - £986 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • 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 / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £158 / night

£1103 - £1589 / 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

18 Photos

Villa / 5 Bedrooms / sleeps 12

3 Nights min stay

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from £95 / night

£662 - £1412 / 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

18 Photos

B&B / 3 Bedrooms / sleeps 2

1 night min stay

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from £48 / night

£335 - £387 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Relax, eco sostenibilità, campagna, piscina e buona tavola, sono le caratteristiche che ci distinguono e che vi faranno apprezzare maggiormente le bellezze di questa parte della Toscana.  …see more

23 Photos

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

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from £63 / night

£438 - £489 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
AGRITURISMO, BED AND BREAKFAST, CASTIGLION FIORENTINO, PISCINA, BARBECUE, MOUNTAIN BIKE, OLIO EXTRA VERGINE DI OLIVA, ANIMALI AMMESSI, SPAZIO GIOCO BIMBI, COLAZIONE.  …see more

11 Photos

Townhouse / 2 Bedrooms / sleeps 5

2 Nights min stay

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from £48 / night

£331 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Come si arriva alla Fenice: dall'autostrada A1, uscita Monte San Savino si raggiunge Castiglion F.no dove si arriva alla ss n°71, qui si prosegue a destra in direzione Perugia e, al terzo semaforo, si svolta a sinistra seguendo le indicazioni per S. Cristina. Dopo circ  …see more

7 Photos

Townhouse / 2 Bedrooms / sleeps 5

2 Nights min stay

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from £32 / night

£221 - £331 / 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

8 Photos

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £141 / night

£981 - £2745 / 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

23 Photos

Farmhouse / 4 Bedrooms / sleeps 10

3 Nights min stay

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from £142 / night

£993 / 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 At the dining room of the homeowner you can book dinners made with local produce.  …see more

21 Photos

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £165 / night

£1155 - £2052 / 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

24 Photos

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £104 / night

£728 - £1096 / 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

Farmhouse / 2 Bedrooms / sleeps 4

Short stays welcome

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from £54 / night

£375 - £758 / 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
A few kilometres from Castiglion Fiorentino and Cortona, on the way up the slopes of the Montanina hill, at the top of which the ruins of an ancient castle can be seen through the vegetation, this typical farmhouse has recently been renovated while still maintaining its  …see more

36 Photos

Apartment / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £92 / night

£640 - £949 / 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

20 Photos

Villa / 4 Bedrooms / sleeps 9

Excellent 5/5 

4 Nights min stay

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from £121 / night

£842 - £2420 / 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 / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

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from £199 / night

£1387 - £2592 / 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

24 Photos

Villa / 4 Bedrooms / sleeps 11

Excellent 5/5 

3 Nights min stay

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from £158 / night

£1103 - £2648 / 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

24 Photos

Cottage / 2 Bedrooms / sleeps 4

Excellent 5/5 

Short stays welcome

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from £67 / night

£468 - £687 / 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

24 Photos

Cottage / 2 Bedrooms / sleeps 4

Excellent 5/5 

Short stays welcome

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from £76 / night

£530 - £650 / 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 property is great for half term school holidays as well as the longer summer family holidays in Tuscany.  …see more

24 Photos

Cottage / 3 Bedrooms / sleeps 5

Very Good 4.5/5 

Short stays welcome

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from £76 / night

£530 - £782 / 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

23 Photos

Condo / 1 Bedroom / sleeps 2

Excellent 5/5 

7 Nights min stay

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from £63 / night

£435 - £538 / 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

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

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from £97 / night

£675 - £1690 / 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
Villa Grazia has all the warm characteristic of an ancient Tuscan farmhouse. The renovation, has been completed retaining all original features. High-ceilings with chestnut beams, and terra-cotta floors set the seen of this cosy family vacation home.  …see more

13 Photos

Villa / 5 Bedrooms / sleeps 10

Very Good 4.5/5 

7 Nights min stay

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from £149 / night

£1043 - £1767 / 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

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

24 Photos

Farmhouse / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £197 / night

£1375 - £2362 / 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

Farmhouse / 6 Bedrooms / sleeps 13

7 Nights min stay

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from £144 / night

£1003 - £1756 / 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

15 Photos

Apartment / 1 Bedroom / sleeps 3

3 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

24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £368 / night

£2574 - £5148 / 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

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

24 Photos

Farmhouse / 9 Bedrooms / sleeps 22

3 Nights min stay

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from £267 / night

£1867 - £3717 / 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

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

5 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

4 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

13 Photos

Apartment / 2 Bedrooms / sleeps 4

5 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

26 Photos

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

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from £164 / night

£1146 - £2183 / 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

16 Photos

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £211 / night

£1471 / 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

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