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35 Holiday homes in Cortona

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35 Results  |  
21 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £237 /night

£1654 - £1993 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Nestled into a Tuscan hillside, a few minutes drive or leisurely walk into the historic and vibrant City of Cortona, Villa Rosa is a 2 bedroom, 2 bathroom, fully furnished private house with essential pool and wi-fi. Couples love it, families love it. It is heaven.  …see more

14 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £237 /night

£1654 - £1993 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Nestled into a Tuscan hillside, a few minutes drive or leisurely walk into the historic and vibrant City of Cortona, Villa Rosa is a 2 bedroom, 2 bathroom, fully furnished private house with essential pool and wi-fi. Couples love it, families love it. It is heaven.  …see more

14 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £84 /night

£583 - £848 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Located in the heart of the Tuscan countryside, Borgo di Vagli is a quaint, meticulously restored 14th century Hamlet surrounded by a protected area of olive groves, fruit trees and ancient oaks.  …see more

Featured properties

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £63 /night

£440 - £616 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
"Il Villino di Cortona", is a cozy house nestled in the heart of val di chiana: in an area rich in history and cultural attractions. Tuscany holiday house. (exclusive use property, house, pool, garden). The veranda is ideal to enjoy a rich and tasty breakfast, or to immerse yourself in the reading a good book.  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £141 /night

£984 - £1800 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Your very own piece of medieval Cortona! Gracious living in this superbly equipped, spacious "home from home" at the pedestianised heart of town. Enjoy a welcome retreat from the rigours of your day's sightseeing, before an evening of fine dining and quality shopping. Cortona continues to host immunerable weddings in its medieval town hall, with the famous photogenic steps!  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

6 Nights min stay

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from £85 /night

£594 - £764 / week

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Key info:

  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Charming small villa near Cortona, large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. The perfect base to explore Tuscany and Umbria. Very comfortable, fully equipped. Stunning countryside. Free GPS, Italian cell phone,laptop. Swimming pools/thermal spas. Great restaurants. Short walk to village.  …see more

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

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from £134 /night

£933 - £1272 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Nestled in the foothills of Cortona, overlooking the Val di Chiana and Mount Amiata. The perfect base for exploring the beautiful regions of Tuscany and Umbria or simply relaxing, surrounded by nature.  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £119 /night

£827 - £1516 / week

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Key info:

  • Nearest beach 22 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Charming stone farmhouse with original features. Perfect for family holidays. Private pool, table tennis and Wifi Internet. Beautiful countryside views. Only 2 kilometres from a village with shops and restaurant. Sought after location on the Tuscany-Umbria border.  …see more

20 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £46 /night

£318 - £523 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Halfway up a hill, under the watchful eye of the beautiful town of Cortona, lies the ancient and noble Villa Serena, surrounded by olive groves and an old rustic park. Here, among centuries-old tranquility, you can relax and enjoy stately cypress and pine trees along...  …see more

20 Photos

House | 3 Bedrooms | sleeps 7

1 night min stay

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from £67 /night

£464 - £920 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Livio B is a spacious two-story apartment made of stone. It sleeps seven people. It is appoximately 90 square meters (970 square feet)  …see more

20 Photos

House | 1 Bedroom | sleeps 3

1 night min stay

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from £52 /night

£360 - £520 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Fastia B is a welcoming apartment. It sleeps three people. It is appoximately 50 square meters (540 square feet)  …see more

20 Photos

House | 1 Bedroom | sleeps 2

1 night min stay

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from £32 /night

£220 - £310 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Fastia C is a graceful cottage. It sleeps two people. It is appoximately 40 square meters (430 square feet)  …see more

15 Photos

House | 1 Bedroom | sleeps 3

7 Nights min stay

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from £45 /night

£314 - £584 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Residence Il Casale lies near Cortona, on wooded hills above a valley. From here you have a wonderful view of the famous Etruscan city. Residence Il Casale was originally a farm dating from the 16th century. The original main building as well as several outbuildings ...  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £50 /night

£344 - £664 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Residence Il Casale lies on a wooded hillside near Cortona, in a valley. From here you have a wonderful view of the famous Etruscan city. The Residence Il Casale was originally a farm dating from the 16th century. The old main building and several outbuildings are si...  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £135 /night

£941 - £1375 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated in the middle of a hill, under the watchful eye of the beautiful town of Cortona, you will find the ancient, noble Villa Serena, surrounded by olive groves and an old rustic park. Here you can relax and enjoy the stately cypress trees, the pine trees and a m...  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £50 /night

£348 - £720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Livio C is a welcoming apartment surrounded by meadows and by green hills. It sleeps six people. It is appoximately 80 square meters (860 square feet). It features a shared swimming pool, a shared garden, a reserved outdoor area and winter heating  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £50 /night

£348 - £720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Livio A is a graceful apartment surrounded by the vegetation. It sleeps six people. It is appoximately 80 square meters (860 square feet). It features a shared swimming pool, a private terrace, a shared garden and winter heating. You will be roughly 3.5 km (2  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £58 /night

£400 - £720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Grifone A is a graceful two-story apartment in the characteristic style of the Tuscan countryside. It sleeps six people. From Casa Grifone A you will have a pleasant view of the Tuscan countryside and of the hills  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £58 /night

£400 - £720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Grifone B is a graceful one-story apartment surrounded by meadows and by green hills. It sleeps six people. From Casa Grifone B you will have a fascinating view of the Tuscan countryside. Casa Grifone B is 90 square meters (970 square feet)  …see more

12 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £46 /night

£318 - £584 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Halfway up a hill, under the watchful eye of the beautiful town of Cortona, lies the ancient and noble Villa Serena, surrounded by olive groves and an old rustic park. Here, among centuries-old tranquility, you can relax and enjoy stately cypress and pine trees along...  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £57 /night

£396 - £760 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Livio D is a graceful two-story apartment surrounded by meadows and by green hills. It sleeps six people. It is appoximately 90 square meters (970 square feet). It features a shared swimming pool, a shared garden, a reserved outdoor area and winter heating  …see more

20 Photos

House | 1 Bedroom | sleeps 4

1 night min stay

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from £56 /night

£390 - £580 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Fastia A is a graceful apartment. It sleeps four people. From Villa Fastia A you will enjoy a pleasant view of the Tuscan hills and of the greenery. Villa Fastia A is 60 square meters (645 square feet)  …see more

15 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £45 /night

£309 - £461 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Originally a farm dating from the 16th century, Residence Il Casale lies near Cortona, on wooded hills above a valley. From here you have a wonderful view of the famous Etruscan city. The old main building as well as several outbuildings are situated along two sides ...  …see more

20 Photos

House | 3 Bedrooms | sleeps 7

1 night min stay

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from £58 /night

£400 - £800 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Grifone C is a characteristic two-story apartment surrounded by the vegetation. It sleeps seven people. From Casa Grifone C you will have a splendid view of the surrounding countryside. Casa Grifone C is 130 square meters (1400 square feet)  …see more

20 Photos

House | 3 Bedrooms | sleeps 9

1 night min stay

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from £118 /night

£820 - £1230 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Fastia Grande is a splendid apartment that covers the entire top floor of a villa. It sleeps nine people. From Villa Fastia Grande you will enjoy a pleasant view of the Tuscan hills and of the greenery  …see more

9 Photos

House | 2 Bedrooms | sleeps 5

1 night min stay

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from £154 /night

£1075 - £1737 / week

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Key info:

  • Not suitable for children
  • Pets welcome

"Casa il Giardino", 3-room house 80 m2 on 2 levels, on the ground floor, fully renovated, nice, tasteful, stylish and cosy furnishings: living/dining room with 1 sofa bed (140 cm), open fireplace, dining table and satellite-TV. Exit to the garden. 1 double bedroom. Exit to the  …see more

14 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £145 /night

£1015 - £1385 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Only a few minutes from the proud and ancient hill town of Cortona, lays the tiny hamlet of Pergo. A dirt road leads you to this spacious holiday house, surrounded by well-kept lawns, olive groves and a mixed vegetation of trees and rose bushes. The living room, with...  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £63 /night

£435 - £586 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This pretty, rustic, air-conditioned holiday cottage is located in a small hamlet consisting of 4 stone-built houses on a hill overlooking the valley. This property is one of 3 holiday rentals and the fourth house belongs to the owner. With traditional furnishings an...  …see more

19 Photos

House | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £74 /night

£516 - £765 / week

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Key info:

  • Not suitable for children
  • No pets allowed
The beautifully restored farmhouse is set in the hills on the border between Tuscany and Umbria. This property comes with a small, private, above-ground swimming pool and beautiful views over the countryside. This is a very well-equipped lawn, equipped porch for outd...  …see more

16 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £55 /night

£382 - £526 / week

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Key info:

  • Great for children of all ages 5
  • No pets allowed
Accogliente, caratteristica abitazione in pietra, situata nel centro storico della città etrusca di Cortona, celebre per il suo passato che ancora vive tra i suoi vicoli. Base ideale per visitare Arezzo, Montepulciano, Pienza e le suggestive campagne toscane e umbre.  …see more

6 Photos

House | 2 Bedrooms | sleeps 6

5 Nights min stay

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from £85 /night

£594 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
La casa vacanza è perfetta per trascorrere vacanze ideali in una delle cittadine più belle e frizzanti della toscana. Unisce la comodità di vivere nel centro storico al piacere di avere 2 spazi esterni privati in cui rilassarsi. Tutta la Toscana e Umbria è max 2 ore  …see more

5 Photos

House | 3 Bedrooms | sleeps 6

Short stays welcome

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from £122 /night

£848 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
-  …see more

8 Photos

House | 6 Bedrooms | sleeps 6

Very Good 4/5 

Short stays welcome

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from £122 /night

£848 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
-  …see more

19 Photos

House | 1 Bedroom | sleeps 3

Min stay varies

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from £60 /night

£416 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Appartamento in agriturismo: casa unica appena ristrutturata con comodi servizi, immersa nel parco e adiacente alla piscina. ortaggi, olio extra vergine e vinsanto di produzione della casa  …see more

21 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

Min stay varies

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from £103 /night

£720 - £1360 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome.  …see more