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43 Holiday homes in Castiglion Fiorentino

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43 Results  |  
18 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £171 /night

£1197 - £2309 / 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

16 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £31 /night

£214 / 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

14 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £55 /night

£385 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Historical Centre Apartment + terrace in centre WIFI  …see more

Featured properties

11 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £43 /night

£300 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Tuscany Holiday House  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £178 /night

£1240 - £2719 / 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

18 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £110 /night

£770 / 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

23 Photos

Townhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £49 /night

£342 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Pets welcome
La struttura conserva i pavimenti in cotto e graniglia originali come le porte a doppia anta in massello e gli alti soffitti con travi a vista. Numerosi i parcheggi gratuiti a poca dstanza. Tutte le bellezze di interesse artistico e storico sono raggiungibili a piedi. Vivrete appieno la quieta atmosfera di un borgo medievale che si anima a maggio nel periodo del Palio  …see more

11 Photos

Townhouse | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £55 /night

£385 - £471 / 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

15 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £184 /night

£1283 / 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

8 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £15 /night

£103 / 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

14 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £147 /night

£1025 - £2138 / 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

17 Photos

Villa | 4 Bedrooms | sleeps 12

4 Nights min stay

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from £228 /night

£1590 - £3286 / 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

13 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £52 /night

£360 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Large Sunny Studio aprtment in Historical Centre with Garden and Wifi  …see more

21 Photos

House | 4 Bedrooms | sleeps 11

6 Nights min stay

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from £106 /night

£736 / 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

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

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

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

15 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

Short stays welcome

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from £75 /night

£525 - £775 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Quiet location in old Tuscan villa. Large pool, spacious apartment with a lovely walk to shop and bar, Quiet peaceful location. Clean and bright family holiday rental. Lots of help if you need it with travel plans including visits to vineyards, cooking classes and more The old stone pizza oven is available for pizza and other barbecue specialties.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £75 /night

£525 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
2 bedroom family apartment in Tuscany, with pool. Easy access to towns and the closest shop/bar and restaurant are within an easy stroll. A perfect family holiday with lots to do here and in our surrounding hill towns. Wine tours, Cooking classes and much more.  …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
  • 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 £78 /night

£542 - £642 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable for children over
  • 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

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
  • 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

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £182 /night

£1274 - £2650 / 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

15 Photos

Studio | sleeps 3

Excellent 5/5 

1 night min stay

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from £43 /night

£300 / week

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Key info:

  • Nearest beach 150 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Big and bright studio apartment in Montecchio Vesponi, Castiglion Fiorentino with parking and WiFi  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £168 /night

£1170 - £2250 / 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

20 Photos

Manor House | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £367 /night

£2565 / 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £137 /night

£958 - £1967 / 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

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

20 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £224 /night

£1568 - £2613 / 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

24 Photos

Villa | 4 Bedrooms | sleeps 11

Excellent 5/5 

3 Nights min stay

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from £173 /night

£1210 / week

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Key info:

  • Nearest beach 128 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

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

20 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

4 Nights min stay

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from £140 /night

£979 - £2813 / 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

15 Photos

Cottage | 4 Bedrooms | sleeps 15

2 Nights min stay

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from £135 /night

£941 - £1197 / 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

6 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £74 /night

£513 - £599 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
Apartament for a family with all confortability. Ideal holiday for visit the best city of Tuscany.  …see more

23 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £73 /night

£509 - £569 / 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

18 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

Min stay varies

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from £46 /night

£317 - £342 / 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

14 Photos

B&B | 1 Bedroom | sleeps 2

Excellent 5/5 

Min stay varies

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from £49 /night

£342 - £411 / week

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Key info:

  • Not suitable for children
  • Car essential
  • Some pets are welcome - please contact the owner
tuscany, agriturismo, cortona, Arezzo, Castiglion Fiorentino Within 550 meters is a local bar and grocery store. The medieval town of Castiglion Fiorentino is about 5 km  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

Min stay varies

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from £97 /night

£676 - £941 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The farm is nestled in the enchanting Tuscan hillside of the Val di Chio located between Arezzo and Cortona  …see more

24 Photos

House | 1 Bedroom | sleeps 2

Min stay varies

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from £63 /night

£441 - £492 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
Agriturismo in posizione collinare dominante la Valle di Chio. A pochi kilometri da importanti città d'arte come Firenze, Siena, Perugia. Piscina 9x15. Maneggio 1km campi da tennis 1km  …see more

7 Photos

Townhouse | 2 Bedrooms | sleeps 5

Min stay varies

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from £37 /night

£257 - £385 / 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

17 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £56 /night

£386 / week

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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

19 Photos

Villa | 4 Bedrooms | sleeps 10

Min stay varies

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from £191 /night

£1336 - £2062 / 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

House | 6 Bedrooms | sleeps 13

Excellent 5/5 

7 Nights min stay

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from £357 /night

£2499 / 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