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58 Results  |  
21 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £169 /night

£1183 - £2410 / 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

17 Photos

Barn | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £132 /night

£920 - £1183 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

1 night min stay

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from £46 /night

£319 - £381 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Ideal to relax your body and your mind: beatiful landscape and trekking area; ideal place to visit all the central Italy: Arezzo, Cortona, Siena, Perugia, Assisi, La Verna, Camaldoli, Florence and also Rome.  …see more

Featured properties

18 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £226 /night

£1577 - £2804 / 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

12 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £151 /night

£1052 - £2191 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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

16 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £77 /night

£538 - £794 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

15 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

Short stays welcome

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from £77 /night

£538 - £794 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
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

21 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £54 /night

£372 - £703 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
The Madonnina Agriturismo is very quiet, in a very sunny location with wonderful view over the Valdichiana valley.  …see more

16 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £110 /night

£765 - £984 / 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

18 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £71 /night

£491 - £616 / 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

24 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £80 /night

£556 - £815 / 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 £161 /night

£1124 - £1905 / 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

24 Photos

Cottage | 3 Bedrooms | sleeps 5

Very Good 4/5 

Short stays welcome

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from £80 /night

£556 - £815 / 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

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £77 /night

£534 - £600 / week

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Key info:

  • Nearest beach 23 km
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
In the shadows of Montechio castle, this lovely Tuscan "home" has 3 bedrooms and is ideal for those who would like some piece and tranquility and at the same time access to the culture, food and natural beauty that Tuscany and Umbria has to offer.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £235 /night

£1645 - £2934 / 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

23 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £207 /night

£1447 - £2273 / 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

13 Photos

Apartment | 1 Bedroom | sleeps 4

4 Nights min stay

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from £56 /night

£389 / week

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Key info:

  • Suitable 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

23 Photos

Condo | 1 Bedroom | sleeps 2

7 Nights min stay

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from £72 /night

£500 - £615 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
This romantic garden cottage, sits in the sleepy hamlet of Orzale and provides the perfect place to unwind and enjoy Tuscany. Simple, but charming accommodation - and a private pool. Capuchi cottage is immersed in the beautiful Tuscan country side. Private and cosy, perfect for a quiet romantic time in Tuscany  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £80 /night

£556 - £815 / 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

21 Photos

House | 4 Bedrooms | sleeps 11

6 Nights min stay

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from £108 /night

£754 - £1796 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Strategic location to visit TUSCANY. Full packages available with tours (wine, food, historical, religious and many others).  …see more

17 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £54 /night

£374 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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

12 Photos

House | 6 Bedrooms | sleeps 13

Excellent 5/5 

7 Nights min stay

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from £318 /night

£2221 - £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

13 Photos

Apartment | 2 Bedrooms | sleeps 4

Short stays welcome

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from £99 /night

£693 - £964 / 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

16 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £182 /night

£1271 - £2786 / week

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Late Deal: save up to €451 (approx. £373)

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

14 Photos

B&B | 1 Bedroom | sleeps 2

Excellent 5/5 

3 Nights min stay

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from £50 /night

£350 - £421 / week

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Key info:

  • Not suitable for children
  • Car essential
  • May take pets – please enquire
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

24 Photos

Villa | 4 Bedrooms | sleeps 11

Excellent 5/5 

3 Nights min stay

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from £178 /night

£1240 - £2976 / 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

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £47 /night

£325 - £351 / 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

10 Photos

Villa | 1 Bedroom | sleeps 4

1 night min stay

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from £71 /night

£496 - £562 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This charming, characteristic cottage, lies in open countryside near the medioeval village of Castiglion Fiorentino in Tuscany at just 10km from Cortona.  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 12

Min stay varies

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from £213 /night

£1487 - £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

20 Photos

Villa | 4 Bedrooms | sleeps 9

Excellent 5/5 

4 Nights min stay

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from £136 /night

£947 - £2720 / 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

4 Nights min stay

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from £208 /night

£1451 - £2678 / 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

20 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £139 /night

£970 - £1250 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Belide A is a graceful attic. It sleeps four people. From Casa Belide A you will have a pleasant view of the greenery and of the surrounding countryside. Casa Belide A is 55 square meters (590 square feet)  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £230 /night

£1607 - £2678 / 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

15 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £660 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Sandia A is a characteristic and welcoming apartment. It sleeps three people. From Villa Sandia A you will enjoy a pleasant view of the garden. Villa Sandia A is 40 square meters (430 square feet)  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £115 /night

£800 - £1320 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

19 Photos

Villa | 4 Bedrooms | sleeps 10

Min stay varies

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from £180 /night

£1258 - £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

18 Photos

Villa | 9 Bedrooms | sleeps 18

3 Nights min stay

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from £414 /night

£2893 - £7521 / 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

15 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £660 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Sandia D is a welcoming apartment. It sleeps three people. From Villa Sandia D you will have a pleasant view of the garden. Villa Sandia D is 30 square meters (320 square feet)  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £660 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Sandia C is a cozy and welcoming apartment. It sleeps three people. From Villa Sandia C you will have a nice view of the garden. Villa Sandia C is 35 square meters (375 square feet)  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £215 /night

£1504 - £3133 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 11

7 Nights min stay

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from £136 /night

£946 - £2719 / week

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Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 £79 /night

£553 - £1191 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £172 /night

£1199 - £2505 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 £147 /night

£1025 - £2207 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

15 Photos

Cottage | 4 Bedrooms | sleeps 15

2 Nights min stay

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from £138 /night

£964 - £1928 / 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

6 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £76 /night

£526 - £789 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartament for a family with all confortability. Ideal holiday for visit the best city of Tuscany.  …see more

4 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £51 /night

£351 - £482 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Fragola is ideal apartament for a little family that love travel and visit the beautiful Tuscany.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 15

4 Nights min stay

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from £1 /night

£1 - £4173 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Set in Tuscany Italy, this vacation villa is the ideal place for your holidays. The villa features: a swimming Pool, an internet Connection, a pet friendly space .  …see more

18 Photos

House | 5 Bedrooms | sleeps 11

1 night min stay

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from £269 /night

£1881 - £2439 / 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

10 Photos

Apartment | 2 Bedrooms | sleeps 5

Min stay varies

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from £65 /night

£455 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • Pets welcome
This 2 bedroom, 2.0 bath vacation apartment in Castiglion Fiorentino, Tuscany offers uncompromising style and comfort, and sleeps up to 5 comfortably. It is equipped with everything you need to enjoy your stay. This Apartment is a great vacation rental  …see more