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42 Holiday homes in Castiglion Fiorentino

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42 Results  |  
18 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £315 /night

£2205 - £2714 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Magnificent villa with swimming pool between Arezzo and Cortona  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £45 /night

£314 - £340 / week

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Key info:

  • Suitable 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

13 Photos

Apartment | 2 Bedrooms | sleeps 4

Short stays welcome

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from £96 /night

£670 - £933 / week

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Key info:

  • Swimming pool
  • Suitable 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

Featured properties

16 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £176 /night

£1230 - £2697 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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

21 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £176 /night

£1230 - £2332 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Villa with swimming pool near Cortona, with stunning view over the olive groves and the town of Castiglion Fiorentino  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £43 /night

£297 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
Tuscany Holiday House  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £75 /night

£520 - £768 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
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 | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £68 /night

£476 - £596 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
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

23 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £228 /night

£1592 - £2840 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

Cottage | 3 Bedrooms | sleeps 5

Very Good 4/5 

Short stays welcome

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from £83 /night

£580 - £788 / week

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Key info:

  • Nearest beach 26 km
  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • May take pets – please enquire
  • Private garden
Good value Family Holiday in 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

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £80 /night

£556 - £628 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • May take pets – please enquire
  • 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

13 Photos

Villa | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

7 Nights min stay

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from £156 /night

£1088 - £1844 / week

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Key info:

  • Nearest beach 27 km
  • Swimming pool
  • Suitable 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

16 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £107 /night

£748 - £952 / week

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Key info:

  • Swimming pool
  • Suitable 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

23 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £200 /night

£1400 - £2200 / week

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Key info:

  • Swimming pool
  • Suitable 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 | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £212 /night

£1480 - £2600 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • 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

24 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £83 /night

£580 - £636 / week

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Key info:

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

23 Photos

Villa | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £164 /night

£1144 - £1664 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Holiday villa rentals in Castiglion Fiorentino, just 18 kms away from Arezzo, Italy.andnbsp; The villa is situated in the beautiful Tuscan countryside just 18 Km from Arezzo, 15 Km from Cortona and 60 Km from Siena. A convent of the XIII century recently restored is sit  …see more

21 Photos

House | 4 Bedrooms | sleeps 11

6 Nights min stay

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from £97 /night

£679 - £1739 / week

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Late Deal: save up to €265 (approx. £212)

Key info:

  • Swimming pool
  • Suitable 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

12 Photos

House | 6 Bedrooms | sleeps 13

Excellent 5/5 

7 Nights min stay

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from £357 /night

£2499 - £3239 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

15 Photos

Cottage | 4 Bedrooms | sleeps 15

2 Nights min stay

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from £134 /night

£933 - £1866 / week

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Key info:

  • Swimming pool
  • Suitable 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

24 Photos

Villa | 4 Bedrooms | sleeps 11

Excellent 5/5 

3 Nights min stay

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from £172 /night

£1200 - £2880 / week

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Key info:

  • Nearest beach 128 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • 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

1 night min stay

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from £260 /night

£1820 - £2360 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Magnificent villa in a beautiful hillside position with breathtaking views, close to the medieval walled village of Castiglion Fiorentino.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £115 /night

£804 - £1272 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable 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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £195 /night

£1360 - £1960 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castiglion Fiorentino with 4 bedrooms sleeps 8  …see more

18 Photos

Villa | 9 Bedrooms | sleeps 18

3 Nights min stay

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from £400 /night

£2800 - £7280 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Welcome to the Tuscany wedding villa Michele in Arezzo, Italy that has the capacity ofandnbsp;18 peopleandnbsp;with babysitter and andnbsp;indoor pool facilities. andnbsp;The Tuscan Villa Michele is an old country residence specially remodeled into an exclusive  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £212 /night

£1480 - £2544 / week

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Key info:

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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £164 /night

£1144 - £2632 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castiglion Fiorentino with 4 bedrooms sleeps 9  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

4 Nights min stay

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from £131 /night

£916 - £2632 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

9 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £201 /night

£1404 - £2592 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Casale Fiorentinaandnbsp;is a beautiful stone farmhouse located inandnbsp;Castiglion Florentinoandnbsp;amidst the Tuscan country side with its olive groves and rich vineyards.andnbsp; Theandnbsp;kitchenandnbsp;opens onto the outside dining area, a covered porch  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £208 /night

£1456 - £3032 / week

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Key info:

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

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £166 /night

£1160 - £2424 / week

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Key info:

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

24 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £142 /night

£992 - £2136 / week

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Key info:

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

24 Photos

Villa | 4 Bedrooms | sleeps 11

7 Nights min stay

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from £131 /night

£916 - £2632 / week

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Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
This spacious villa boasts a very traditional Tuscan style, which mingles with many modern amenities, 4 bedrooms, full kitchen and a lovely private garden with swimming pool and splendid views of the surroundings.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £77 /night

£536 - £1152 / week

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Key info:

  • Swimming pool
  • Suitable 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

23 Photos

Apartment | 1 Bedroom | sleeps 2

5 Nights min stay

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from £81 /night

£564 / week

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Key info:

  • Swimming pool
  • Suitable 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

13 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £51 /night

£357 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
Large Sunny Studio aprtment in Historical Centre with Garden and Wifi  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £55 /night

£382 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
Historical Centre Apartment + terrace in centre WIFI  …see more

8 Photos

Guest house | 14 Bedrooms | sleeps 39

2 Nights min stay

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from £61 /night

£424 / week

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Key info:

  • Swimming pool
  • Suitable 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

12 Photos

Villa | 3 Bedrooms | sleeps 8

1 night min stay

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from £85 /night

£594 / week

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Key info:

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

17 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £52 /night

£363 / week

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Key info:

  • Suitable 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

17 Photos

Villa | 4 Bedrooms | sleeps 12

Min stay varies

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from £213 /night

£1490 - £3430 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

19 Photos

Villa | 4 Bedrooms | sleeps 10

Min stay varies

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from £180 /night

£1260 - £2980 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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