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64 Results  |  

from £161 / night

£1127 - £2283 / week

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Excellent 5/5 

24 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

4 Nights min stay

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from £161 / night

£1127 - £2283 / week

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Key info:

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

from £145 / night

£1015 - £1957 / week

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Excellent 5/5 

18 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

3 Nights min stay

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from £145 / night

£1015 - £1957 / week

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Key info:

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

from £300 / night

£2095 - £3055 / week

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Excellent 5/5 

12 Photos

House / 6 Bedrooms / sleeps 13

Excellent 5/5 

7 Nights min stay

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from £300 / night

£2095 - £3055 / week

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Key info:

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

Featured properties

from £151 / night

£1051 - £2305 / week

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Excellent 5/5 

22 Photos

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £151 / night

£1051 - £2305 / week

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Key info:

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

from £44 / night

£305 - £381 / week

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Excellent 5/5 

24 Photos

Farmhouse / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

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from £44 / night

£305 - £381 / week

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Key info:

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

from £83 / night

£580 / week

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Excellent 5/5 

18 Photos

Villa / 3 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £83 / night

£580 / 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

from £37 / night

£254 / week

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Excellent 5/5 

15 Photos

Studio / sleeps 3

Excellent 5/5 

1 night min stay

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from £37 / night

£254 / 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

from £42 / night

£290 - £472 / week

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Excellent 5/5 

23 Photos

Townhouse / 2 Bedrooms / sleeps 5

Excellent 5/5 

1 night min stay

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from £42 / night

£290 - £472 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Pets welcome
L'appartamento ampio e pieno di luce sarà in grado di ispirarvi.  …see more

from £42 / night

£290 - £363 / week

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Excellent 5/5 

8 Photos

Guest house / 14 Bedrooms / sleeps 39

Excellent 5/5 

2 Nights min stay

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from £42 / night

£290 - £363 / 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

from £52 / night

£363 - £508 / week

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Excellent 5/5 

8 Photos

House / 2 Bedrooms / sleeps 4

Excellent 5/5 

1 night min stay

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from £52 / night

£363 - £508 / 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

from £39 / night

£269 - £290 / week

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Excellent 5/5 

18 Photos

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

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from £39 / night

£269 - £290 / week

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Key info:

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

from £83 / night

£580 - £1486 / week

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21 Photos

House / 4 Bedrooms / sleeps 11

6 Nights min stay

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from £83 / night

£580 - £1486 / week

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Key info:

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

from £120 / night

£834 - £979 / week

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15 Photos

Barn / 3 Bedrooms / sleeps 6

3 Nights min stay

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from £120 / night

£834 - £979 / 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

from £114 / night

£798 - £1595 / week

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15 Photos

Cottage / 4 Bedrooms / sleeps 15

2 Nights min stay

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from £114 / night

£798 - £1595 / 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

from £125 / night

£869 - £1790 / week

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14 Photos

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £125 / night

£869 - £1790 / week

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Key info:

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

from £163 / night

£1138 - £2022 / week

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21 Photos

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £163 / night

£1138 - £2022 / week

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Key info:

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

from £363 / night

£2537 - £5073 / week

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24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £363 / night

£2537 - £5073 / week

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Key info:

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

from £156 / night

£1087 - £1566 / week

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24 Photos

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £156 / night

£1087 - £1566 / week

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Key info:

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

from £37 / night

£254 / week

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11 Photos

Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

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from £37 / night

£254 / 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

from £63 / night

£435 - £653 / week

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6 Photos

Apartment / 2 Bedrooms / sleeps 6

3 Nights min stay

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from £63 / night

£435 - £653 / 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

from £143 / night

£1000 / week

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18 Photos

Farmhouse / 4 Bedrooms / sleeps 10

7 Nights min stay

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from £143 / night

£1000 / week

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Key info:

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

Pricing unknown

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Apartment / 1 Bedroom / sleeps 2

Min stay varies

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Pricing unknown

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Key info:

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

from £37 / night

£254 - £472 / week

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5 Photos

Condo / 2 Bedrooms / sleeps 5

1 night min stay

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from £37 / night

£254 - £472 / 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

from £47 / night

£327 / week

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14 Photos

Apartment / 1 Bedroom / sleeps 4

1 night min stay

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from £47 / night

£327 / 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

from £62 / night

£432 - £482 / week

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23 Photos

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

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from £62 / night

£432 - £482 / 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

from £47 / night

£327 / week

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11 Photos

Townhouse / 2 Bedrooms / sleeps 5

2 Nights min stay

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from £47 / night

£327 / 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

from £32 / night

£218 - £327 / week

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7 Photos

Townhouse / 2 Bedrooms / sleeps 5

2 Nights min stay

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from £32 / night

£218 - £327 / 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

from £25 / night

£174 / week

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16 Photos

Apartment / 1 Bedroom / sleeps 4

2 Nights min stay

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from £25 / night

£174 / 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

from £44 / night

£305 / week

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13 Photos

Apartment / 1 Bedroom / sleeps 3

3 Nights min stay

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from £44 / night

£305 / 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

from £54 / night

£374 - £417 / week

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24 Photos

House / 1 Bedroom / sleeps 2

3 Nights min stay

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from £54 / night

£374 - £417 / 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

from £103 / night

£718 - £1080 / week

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24 Photos

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

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from £103 / night

£718 - £1080 / 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

from £119 / night

£830 - £2385 / week

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Excellent 5/5 

20 Photos

Villa / 4 Bedrooms / sleeps 9

Excellent 5/5 

4 Nights min stay

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from £119 / night

£830 - £2385 / 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

from £141 / night

£986 - £1754 / week

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Very Good 4.5/5 

13 Photos

Villa / 5 Bedrooms / sleeps 10

Very Good 4.5/5 

7 Nights min stay

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from £141 / night

£986 - £1754 / week

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Key info:

  • Nearest beach 27 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Just a short distance from the medieval town of Castiglion Fiorentino is "Casa Usignoli". This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms.  …see more

from £94 / night

£653 - £1377 / week

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Very Good 4.5/5 

23 Photos

Villa / 4 Bedrooms / sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £94 / night

£653 - £1377 / week

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Key info:

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

from £197 / night

£1377 - £2573 / week

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Excellent 5/5 

23 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

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from £197 / night

£1377 - £2573 / week

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Key info:

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

from £156 / night

£1087 - £2609 / week

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Excellent 5/5 

24 Photos

Villa / 4 Bedrooms / sleeps 11

Excellent 5/5 

3 Nights min stay

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from £156 / night

£1087 - £2609 / week

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Key info:

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

from £59 / night

£410 - £609 / week

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Very Good 4.5/5 

24 Photos

Villa / 1 Bedroom / sleeps 2

Very Good 4.5/5 

7 Nights min stay

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from £59 / night

£410 - £609 / week

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Key info:

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

from £62 / night

£432 - £535 / week

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Excellent 5/5 

23 Photos

Condo / 1 Bedroom / sleeps 2

Excellent 5/5 

7 Nights min stay

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from £62 / night

£432 - £535 / 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

from £68 / night

£472 - £682 / week

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Excellent 5/5 

15 Photos

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

Short stays welcome

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from £68 / night

£472 - £682 / 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

from £278 / night

£1945 / week

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19 Photos

Villa / 4 Bedrooms / sleeps 10

7 Nights min stay

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from £278 / night

£1945 / week

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Key info:

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

from £68 / night

£472 / week

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16 Photos

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

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from £68 / night

£472 / 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

from £87 / night

£609 - £761 / week

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35 Photos

Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

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from £87 / night

£609 - £761 / 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

from £115 / night

£800 - £1320 / week

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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

from £194 / night

£1355 - £2328 / week

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24 Photos

Farmhouse / 4 Bedrooms / sleeps 8

3 Nights min stay

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from £194 / night

£1355 - £2328 / week

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Key info:

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

from £263 / night

£1840 - £3664 / week

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24 Photos

Farmhouse / 9 Bedrooms / sleeps 22

3 Nights min stay

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from £263 / night

£1840 - £3664 / week

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Key info:

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

from £215 / night

£1500 - £3100 / week

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Villa / 4 Bedrooms / sleeps 12

4 Nights min stay

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from £215 / night

£1500 - £3100 / week

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Key info:

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

from £363 / night

£2537 - £5073 / week

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24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

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from £363 / night

£2537 - £5073 / week

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Key info:

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

from £236 / night

£1649 - £2138 / week

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House / 5 Bedrooms / sleeps 11

7 Nights min stay

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from £236 / night

£1649 - £2138 / week

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Key info:

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

from £70 / night

£486 - £1051 / week

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22 Photos

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

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from £70 / night

£486 - £1051 / 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

from £58 / night

£406 - £558 / week

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Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

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from £58 / night

£406 - £558 / week

View

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

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