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44 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

22 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £168 /night

£1170 - £2565 / 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

Featured properties

12 Photos

House | 6 Bedrooms | sleeps 13

Excellent 5/5 

Min stay varies

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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

15 Photos

Studio | sleeps 3

Excellent 5/5 

1 night min stay

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from £41 /night

£283 / 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

23 Photos

Townhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £47 /night

£323 / 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 distanza. 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

8 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £81 /night

£565 / 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

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

14 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £139 /night

£967 - £1096 / 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

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

15 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £173 /night

£1210 / 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

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

21 Photos

House | 4 Bedrooms | sleeps 11

6 Nights min stay

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from £100 /night

£694 / 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

4 Photos

Condo | 2 Bedrooms | sleeps 5

1 night min stay

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from £52 /night

£363 - £525 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
Ferienwohnung, Campingplatz, Naturpool, Reiten, Biogemüse, Natur, Entspannung, Hunde erlaubt, Pferde willkommen Babybett auf Anfrage, Handtücher (für's Bad) und Bettwäsche vorhanden  …see more

11 Photos

Townhouse | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £52 /night

£363 / 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

24 Photos

House | 1 Bedroom | sleeps 2

Min stay varies

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from £60 /night

£416 - £464 / 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 £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

18 Photos

B&B | 3 Bedrooms | sleeps 2

1 night min stay

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from £53 /night

£367 - £424 / 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

15 Photos

Cottage | 4 Bedrooms | sleeps 15

2 Nights min stay

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from £127 /night

£888 - £1130 / 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

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £69 /night

£480 - £537 / 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

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

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 | 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
  • 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

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

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

24 Photos

Villa | 1 Bedroom | sleeps 2

Very Good 4.5/5 

7 Nights min stay

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from £66 /night

£456 - £678 / 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

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

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

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

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

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

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

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

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

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

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

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