Cortona Villas, Holiday rentals and apartments

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Bagnolo (3)
  • Cantalena (1)
  • Capezzine (2)
  • Cegliolo (4)
  • Centoia (8)
  • Farinaio (5)
  • Fratta Santa Caterina (9)
  • Fratticciola (11)
  • Localita Mucchia (2)
  • Mercatale (7)
  • Mercatale di Cortona (16)
  • Montalla (22)
  • Montanare (10)
  • Montecchio (18)
  • Montecchio, San Lorenzo (2)
  • Pietraia (19)
  • Poggioni (4)
  • Ruffignano (1)
  • Teverina (7)

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718 Holiday homes

22

The Orangery: Cortona holiday villa with private pool and garden - Cortona villa sleeps 5

Province of Arezzo / Cortona

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The Orangery” is a charming and cosy detached house wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely r  …see more

from £169 / night

£733 - £1117 / week

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from £169 / night

(1) Excellent 

19

Agriturismo Poggio del Fabbro - Poggioni villa sleeps 7

Cortona / Poggioni

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
L'agriturismo Poggio del Fabbro è situato in località San Pietro a Dame, frazione del comune di Cortona nella montagna cortonese, a 20km dalla città, in una posizione tranquilla e isolata tra le verdi montagne ad un'altezza di 700m slm al confine tra Toscana e Umbria  …see more

from £111 / night

£773 / week

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from £111 / night

(1) Excellent 

15

Appartamento Luna - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
"Luna" Apartment for 2 person, compose by one bedroom + kitchen + 1 bathroom with shower. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square and grocery. Palazzo Quintani, Is  …see more

from £65 / night

£414 / week

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from £65 / night

(3) Very Good 

11

Splendid flat in Tuscany, pool & breathtaking view - Mercatale di Cortona apartment sleeps 6

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children age 5+
If you take the road which follows the Tuscan-Umbrian border you come to Pierle, a medieval hamlet in the hills between Cortona and Lake Trasimeno, its castle dominating the verdant valley below.Here surrounded by olive groves and woodland of oaks and chestnuts, you wil  …see more

from £108 / night

£647 - £949 / week

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from £108 / night

(1) Very Good 

24

Villa Calcinaio - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
Awarded as one of the prettiest and most comfortable villas in Tuscany, Villa Calcinaio with its private swimming pool stands proudly in Cortona and offers amazing views over the Chiana Valley as well as the Church of "Santa Maria delle Grazie al Calcinaio", from which  …see more

from £68 / night

£470 / week

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from £68 / night

(11) Excellent 

35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

Province of Arezzo / Cortona

7 24 3 nights min

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min
  • Nearest beach 250 km
  • Swimming pool
  • Child friendly
Villa Nobile is a stunning 19th Century classical style villa recently restored authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land. A private avenue of young cypresses bringing you to our doorstep. Tran  …see more

from £65 / night

£475 / week

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from £65 / night

18

Acero, pleasing hilly cottage among olive grove - Cortona cottage sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Acero is a cosy apartment that belongs to a beautiful hillside property, Col di Leccio, an authentic farmhouse where nature and silence dominate. Acero is made up of a double bedroom, a bedroom with twin beds, a bathroom with a shower, a kitchen and a living room. There  …see more

from £69 / night

£475 - £733 / week

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from £69 / night

31

Villa Nello - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Above the wood oven is engraved 1781. Villa Nello was restored in 2001. It develops on three floors, sleeping 8 people, plus a small independent single bedroom with bathroom. The ground floor includes an entrance foyer, adjoining dining room and kitchen leading to a lar  …see more

from £616 / night

£4311 / week

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from £616 / night

(5) Excellent 

30

Villa le Celle del Farinaio: Tuscan home with stunning valley views, swimming pool and trampoline, sleeps fourteen - Farinaio villa sleeps 14

Cortona / Farinaio

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
The cells of the villa Farinaio is situated in a beautiful hilly which overlooks the valley below and it is surrounded by green woods of our own property where you can find numerous hiking trails with different difficulty levels for taking a walk. The villa is completel  …see more

from £185 / night

£1294 - £2587 / week

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from £185 / night

100

Residence Valdichiana - 4 pax - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
4 pax This apartment for rent in Tuscany boasts its own private garden. This apartment of the farmhouse can host up to 4 guest. The country style, the typical warmth of Tuscan hospitality make it a perfect place to experience the flavour of Tuscany. This apart  …see more

from £108 / night

£595 - £768 / week

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from £108 / night

15

Le Casine - Papavero Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £54 / night

£371 - £495 / week

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from £54 / night

(1) Excellent 

12

Villa Cuiano- La Stalla - Mercatale di Cortona apartment sleeps 4

Cortona / Mercatale di Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
If you take the road which follows the Tuscan-Umbrian border you come to Pierle, a medieval hamlet in the hills between Cortona and Lake Trasimeno, its castle dominating the verdant valley below.Here surrounded by olive groves and woodland of oaks and chestnuts, you wil  …see more

from £87 / night

£518 - £776 / week

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from £87 / night

24

Il Casone, magnificent verdant Villa in Tuscany - Cortona villa sleeps 14

Province of Arezzo / Cortona

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Il Casone lies in the open countryside, a few minutes from Cortona. Immersed in a large garden, among the green olive trees and the delicate scent of the roses, this ancient farmhouse has been painstakingly restored and converted into 4 comfortable apartments, character  …see more

from £296 / night

£2069 / week

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from £296 / night

100

Orietta - Cortona villa sleeps 5

Province of Arezzo / Cortona

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
ExteriorsIf it is not inside the charming little villa, guests will definitely want to be enjoying its surroundings. This wonderful retreat is located in the city of Cortona, and the entire area boasts some majestic scenery that can be explored on foot, by bike or by ca  …see more

from £169 / night

£733 - £906 / week

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from £169 / night

100

Flavia - Loggia - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This apartment has one double bedroom with a comfortable queen bed. It has a stunning view of the hills surrounding the large hamlet. It has one large bathroom that is complete with a shower and modern amenities.There is a cozy living room&  …see more

from £86 / night

£427 - £772 / week

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from £86 / night

31

Luxury villa in Cortona - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This magnificent villa is located at 400 m from the lovely town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. This elegant vill  …see more

from £370 / night

£2587 - £4018 / week

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from £370 / night

(9) Excellent 

33

Villa Rosa - Heaven in Tuscany|Pool|WiFi|Cortona - Cortona villa sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant Cortona. Couples love it, families love it. It is heaven. A two bedroom, two bathrooms, fully furnished beautiful  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(1) Excellent 

44

Il Ciliegio - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Wonderful and elegant villa situated in a quiet position on the green hills which surround Cortona.The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.The house is tastefully furnished and is equipped with a  …see more

from £150 / night

£1049 / week

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from £150 / night

(2) Excellent 

88

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £104 / night

£604 - £1026 / week

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from £104 / night

15

Villa Suardi - Teverina villa sleeps 20

Cortona / Teverina

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This magnificent country house is perfect for a family reunion or a group trip as it has 14 bedrooms. The complex has a large garden with a private swimming pool (12x6 m. Deep from 1.20 to 2.00 m), garden furniture, sunbeds and umbrellas. The main villa is divided in  …see more

from £345 / night

£2414 - £3621 / week

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from £345 / night

(5) Excellent 

41

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £67 / night

£465 / week

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from £67 / night

(1) Excellent 

28

Giusi e Dario - Montanare villa sleeps 12

Cortona / Montanare

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
main HouseA charming Tuscan villa designed, decorated and furnished by 'Giusi', the Italian cook who often helps friend Frances Mayes prepare splendid luncheons and dinner parties at Villa Bramasole, near Cortona. Giusi is mentioned and photographed in Frances  …see more

from £339 / night

£2371 - £5561 / week

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from £339 / night

16

Le Casine - Girasole Apartment - Fratta Santa Caterina apartment sleeps 4

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £59 / night

£409 - £552 / week

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from £59 / night

(2) Very Good 

12

Cortona villa in beautiful Tuscan countryside - Cortona villa sleeps 5

Province of Arezzo / Cortona

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The sitting room has an old open fireplace and impressive, ancient wooden beams. Two comfy sofas are a nice modern addition! The dining room is authentic Italian 1950s decor under more seriously ancient ceiling beams. The atmosphere at San Silvestro is one of homely cou  …see more

from £93 / night

£650 - £850 / week

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from £93 / night

84

Fienile/luxury. Private village. Sleeps 5 - Montecchio house sleeps 5

Cortona / Montecchio

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fienile Cottage is a cute detached cottage, situated in its own private garden, with sensational views of olive groves, vineyards, meadows full of sunflowers, poppies and purple cornflowers, spiralling infinitely into the valleys below. It has 1 double bedroom + 1 singl  …see more

from £117 / night

£819 - £949 / week

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from £117 / night

19

Le Casine - Mela Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £51 / night

£352 - £466 / week

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from £51 / night

(1) Excellent 

12

Large Tuscan farmhouse apartment in beautiful Cortona countryside, four bedrooms, pool access - Cortona farmhouse sleeps 6

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
The apartment is independent, and has beautiful piece of ancient furniture own heating system, some of them has a fire-place. This has a own outside space and very well fitted out with garden furniture, all equipped with every thing necessary to be efficient and functi  …see more

Pricing unknown

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Pricing unknown

11

La Sorgente - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Located in a beautiful and very peaceful valley of the Cortonese countryside, but only 10 mins drive from the lively hilltown, this quaint and atmospheric farmhouse has been lovingly restored and tastefully furnished by its Italian-American owners. The property is crad  …see more

from £265 / night

£1850 - £2759 / week

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from £265 / night

15

Cortona walking distance villa - Cortona villa sleeps 5

Province of Arezzo / Cortona

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely small villa is located at 400 m from the charming town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. The villa, 65  …see more

from £99 / night

£690 - £1207 / week

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from £99 / night

100

Curtum - Three-Room - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
These 2 three-roomed apartments can sleep up to 4 people each; and they both boast their own private bathroom with shower and full kitchenette. They also afford one double bedroom and one twin bedroom.Both apartments have their own private outdoor area, and they are equ  …see more

from £189 / night

£741 / week

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from £189 / night

21

Villa Neri - Cortona villa sleeps 12

Province of Arezzo / Cortona

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Neri is situated in San Lorenzo in close driving proximity to Cortona. Cortona is an antique Etruscan town which lies in the heart of the Chiana valley. You can even see the town perched on the hill in front of you. The position is isolated and it will offer you c  …see more

from £112 / night

£776 - £1121 / week

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from £112 / night

26

Villa la Bozza - Montalla farmhouse sleeps 14

Cortona / Montalla

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
I our farm we have a number of houses left intact in theyr original stile.Viila la Bozza is ancient building near a small country village in the country in front of Cortona.Divided in 2 apartments of the same size, completely independent from each other you will have a  …see more

from £276 / night

£1462 - £2413 / week

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from £276 / night

(2) Excellent 

22

House in Central Cortona with Private Garden - Cortona cottage sleeps 6

Province of Arezzo / Cortona

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Our house is spacious and full of light - a perfect cool retreat after a warm summer day's exploration in Tuscany. Great for two love birds or a couple with a child, this accommodation in Cortona even has its own little walled garden, where you can sit and chat in  …see more

from £69 / night

£483 / week

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from £69 / night

(1) Excellent 

6

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

(1) Good 

37

Fattoria Le Chianacce - La Mucchia. Cortona - Cortona apartment sleeps 10

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Set in the verdant hills of the Valdichiana on the border between the Provinces of Arezzo and Siena the Fattoria delle Chianacce is a typical farmhouse built in the last century. These farms produced some of the very best beef and pork in the area and many continue to d  …see more

from £78 / night

£544 - £863 / week

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from £78 / night

22

cortona holiday villa with swimming pool and wi fi - Cortona cottage sleeps 6

Province of Arezzo / Cortona

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful holiday home near Cortona, is located at a 15 min drive (15km) from this famed Etruscan and medieval town, main cultural and artistic centre of the Val di Chiana after Arezzo. The cottage is the outbuilding of an old farmhouse, dating back to the 18th cen  …see more

from £114 / night

£794 - £1457 / week

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from £114 / night

25

Casale della Torre - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa Casale Mulino is a property situated on about 10 acres of terraced land which has olive tree groves and vineyards. It's a perfect starting point for panoramic walks or biking. The spectacular panorama that this villa offers will be the missing ingredient for  …see more

from £353 / night

£2466 - £3518 / week

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from £353 / night

27

Sopra di Brena - Teverina farmhouse sleeps 8

Cortona / Teverina

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Sopra di Brena is located in San Pietro a Dame, about 20 kms from Cortona. The villa is an old restored farmhouse which enjoys stunning, panoramic views. It is surrounded by vinyards (around 1,350 Pinot Nero vines), which have been producing a highly-prized wine since  …see more

from £177 / night

£1233 - £1604 / week

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from £177 / night

29

Villa Le Contesse - Cortona villa sleeps 20

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Le Contesse is a beautiful independent villa lying on a hillside, a few minutes from the Etruscan town of Cortona. A large park with holm-oaks and secular trees surrounds the villa, which commands a stunning view over the Valdichiana. Le Contesse has been furnishe  …see more

from £555 / night

£3880 - £4311 / week

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from £555 / night

17

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £69 / night

£259 - £393 / week

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from £69 / night

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