Cortona Villas, Holiday rentals and apartments

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Location

  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
  • All locations
  • Bagnolo (3)
  • Cantalena (1)
  • Capezzine (2)
  • Cegliolo (4)
  • Centoia (8)
  • Farinaio (5)
  • Fratta Santa Caterina (9)
  • Fratticciola (11)
  • Localita Mucchia (2)
  • Mercatale (8)
  • 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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745 Holiday homes

24

Cortona / Montanare

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly

 …see more

from £69 / night

£475 - £518 / week

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from £69 / night

4

Province of Arezzo / Cortona

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£388 / week

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from £61 / night

24

Casale Girifalco - Cortona house sleeps 12

Province of Arezzo / Cortona

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Private garden
Villa Casale Girifalco, 16th century, is a charming country house, located on an extensive ground (nearly 5 hectares) with a stunning view of the Valdichiana valley. Perched on the terraced slopes of olive groves, it guarantees you complete privacy and tranquility, whil  …see more

from £390 / night

£2725 - £3518 / week

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from £390 / night

5

Province of Arezzo / Cortona

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £68 / night

£475 / week

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from £68 / night

10

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £50 / night

£345 / week

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from £50 / night

8

La Tesa Grano - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees.Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating e  …see more

from £35 / night

£500 - £742 / week

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from £35 / night

42

La Villa di Costantino - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa di Costantino is a typical Tuscan stone built manor, surrounded by a large garden and located in a beautiful spot at the bottom of the hill of the Etruscan old town of Cortona that offers outstanding views over the Valdichiana. The house is spacious and welcoming,  …see more

from £192 / night

£1294 - £2716 / week

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from £192 / night

5

Cortona / Pietraia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £122 / night

£853 / week

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from £122 / night

11

Cortona / Pietraia

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £95 / night

£664 / week

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from £95 / night

100

Nelly - Cortona villa sleeps 10

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
ExteriorsThis beautiful and cozy villa in Cortona has three floors and can accommodate up to 10 people. It has a 3.5x7.5 swimming pool situated amongst terraced olive groves overlooking the Valdichiana. The 40sq-m covered terrace has a large table with room for 12 peopl  …see more

from £286 / night

£2000 - £3218 / week

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from £286 / night

24

Province of Arezzo / Cortona

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

 …see more

from £50 / night

£345 / week

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from £50 / night

38

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 15 km
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £173 / night

£1121 / week

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from £173 / night

23

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£388 - £518 / week

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from £61 / night

22

La Mucchia villa in Tuscany 3 - Cortona apartment sleeps 6

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This suite is on the first floor benefits from the best views of Chiana Valley and Cortona, and opens into a spacious living area with a large authentic wood burning fire place, and spectacular views over the countryside. There is a fully equipped kitchen and 2 double b  …see more

from £127 / night

£888 / week

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from £127 / night

15

Province of Arezzo / Cortona

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £99 / night

£604 / week

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from £99 / night

(1) Excellent 

83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 18 km
  • Swimming pool

 …see more

from £87 / night

£518 - £845 / week

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from £87 / night

95

Cerro-Castagna/luxury. Private village. Sleeps 6 - Montecchio house sleeps 6

Cortona / Montecchio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cerro + Castagna Cottage make up one extremely large apartment with a covered terrace/verandah - seats 6. Not only are there 2 double bedrooms + 2 bathrooms, there are also 2 sitting/dining rooms, each with a fully fitted kitchen, one of which is very large with a firep  …see more

from £111 / night

£776 - £949 / week

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from £111 / night

5

LE MURA ETRUSCHE - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
" IL FASCINO DELLE MURA ETRUSCHE-MEDIEVALI, UNO STUPENDO E RILASSANTE PANORAMA SULLA VALDICHIANA,UNA STRUTTURA DEL 1200 ARREDATA CON AMORE TRA L'ANTICO E IL MODERNO, UN GIARDINO CHE POGGIA SOPRA LE MURA ETRUSCHE, DA CUI PRENDE IL NOME LA STRUTTURA, IN PROSSIMITA' DI POR  …see more

from £80 / night

£561 / week

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from £80 / night

31

Fattoria Le Chianacce - Il Balzo. Cortona - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • 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 £39 / night

£268 - £423 / week

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from £39 / night

(1) Excellent 

64

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £61 / night

£423 / week

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from £61 / night

8

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £68 / night

£475 / week

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from £68 / night

34

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £44 / night

£216 - £380 / week

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from £44 / night

100

Silvia - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
ExteriorsThis fabulous retreat is situated in the city of Cortona, which dominates Val di Chiana. The strategic location allows guests to enjoy the splendid views of vineyards and olive groves as well as some majestic scenery that can be explored on foot, by bike or by  …see more

from £431 / night

£2500 - £3664 / week

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from £431 / night

4

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £68 / night

£475 / week

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from £68 / night

7

Cortona / Pietraia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £106 / night

£650 - £2099 / week

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from £106 / night

15

Dardano - Montalla house sleeps 8

Cortona / Montalla

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
It's a characteristic middle age tower, it's origins can be leaded up around the year 1000 A.C. (The building is rises nearby the Etruscan town of Cortona). We wanted to give it the name of Dardano by the way the legend tells that this mythological character w  …see more

from £234 / night

£1638 / week

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from £234 / night

(2) Excellent 

22

Casina via Iannelli - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets
Casina via Iannelli è una piccola abitazione medioevale (quattordicesimo secolo) dotata di tutti i confort moderni.Si trova nel centro storico di Cortona in una delle strade più caratteristiche della città che si presenta ancora pressoché immutata dal medioevo. Il v  …see more

from £69 / night

£483 / week

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from £69 / night

78

Stalla/luxury, private village, sleeps 2 - Montecchio house sleeps 2

Cortona / Montecchio

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stalla Cottage is an incredibly romantic, detached cottage with one bedroom + 1 bathroom. It opens onto a private garden with ecstatically beautiful views across the valleys that undulate into a depthless abyss of olive groves, orchards, honey fields of yellows, reds an  …see more

from £13 / night

£87 - £604 / week

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from £13 / night

4

Cortona / Pietraia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £117 / night

£815 / week

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from £117 / night

20

Cortona - 60137001 - Cortona apartment sleeps 8

Province of Arezzo / Cortona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Charming apartments created by the restoration of an historical building situated in the center of the beautiful town of Cortona. This property has been carefully restored with its original architectural features and its ancient charm preserved and turned into 2 nice ac  …see more

from £267 / night

£1556 - £2032 / week

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from £267 / night

20

Cortona - 41349002 - Cortona farmhouse sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Nice complex comprising 2 small independent stone villas which have been recently restored. This property is situated in panoramic location on the hills surrounding the beautiful medieval town of Cortona which is only 10 km away. Both villas offer comfortable interiors  …see more

from £62 / night

£433 - £919 / week

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from £62 / night

(3) Excellent 

43

Tuscany Private Home In Cortona, WiFi, Pool, Views - Cortona house 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
Villa Rosa is a private home nestled in the hillside of the historic and vibrant hill top town of Cortona. A few minutes drive or a leisurely stroll into the City of Cortona, with expansive views over the valley to the distance shores of Lake Trasimeno Villa Rosa is  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

49

Province of Arezzo / Cortona

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £78 / night

£544 / week

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from £78 / night

4

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £63 / night

£435 / week

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from £63 / night

52

Eugenio, charming hill Villa (13 people) - Cortona villa sleeps 13

Province of Arezzo / Cortona

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Surrounded by the gentle hills which frame the medieval town of Cortona, Villa Eugenio will assure you a peaceful vacation in the heart of Tuscany. This beautiful 17th century Tuscan farmhouse has been painstakingly restored and turned into a warm and welcoming country  …see more

from £270 / night

£1884 - £3116 / week

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from £270 / night

20

C Di Masino - 57916001 - Fratticciola farmhouse sleeps 4

Cortona / Fratticciola

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful and charming ancient property situated in quiet and panoramic location in the hills surrounding Cortona. This property has been recently restored with its ancient architectural features preserved and converted into 9 appealing apartments, all of which offer ta  …see more

from £105 / night

£569 - £786 / week

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from £105 / night

27

Cortona / Montecchio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £55 / night

£379 - £783 / week

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from £55 / night

26

Agriturismo Villa Giarradea - Cortona house sleeps 15

Province of Arezzo / Cortona

6 15 2 nights min

  • 6 bedrooms
  • Sleeps 15
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
L'Agriturismo Villa Giarradea è una magnifica residenza signorile della fine del 600. Completamente ristrutturata mantenendo l'aspetto esterno originale (la villa è protetta dalle "belle arti"), la struttura è immersa nel verde della campagna Cortonese. Villa Giarrad  …see more

from £52 / night

£363 / week

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from £52 / night

31

Villa Barbara - Cortona villa sleeps 6

Province of Arezzo / Cortona

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
Villa Barbara is situated on the top of a hill kissed by the sun and caressed by the stars. Skilfully restored to keep its ancient charm untouched, it attracts with its solemn dignity and with its remarkable environmental landscaping. Completely furnished following the  …see more

from £222 / night

£1552 - £1983 / week

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from £222 / night

8

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £87 / night

£569 / week

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from £87 / night

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