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148 Holiday homes in Cortona

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148 Results  |  
20 Photos

Villa | 7 Bedrooms | sleeps 15

Short stays welcome

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from £343 /night

£2400 - £2900 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful farmhouse at the foot of Cortona,surrounded by 7000sqm of land cultivated with olive and fruit trees. Located in the village of Pergo, famous for its prestigious villas and farmhouses of which is scattered and of which it is part.  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £58 /night

£404 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
agriturismo cortona teccognano beppe toscana cucina tipica Wi fi piscina  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £381 /night

£2662 - £4194 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
An unforgettable vacation in Cortona, in a splendid luxury villa with all comforts and facilieties. Luxury villa with swimming pool and air conditioned in Corton  …see more

Featured properties

25 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £319 /night

£2228 - £3428 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Villa is placed in the beautiful and striking Tuscan countryside, surrounded by olive trees and vineyard:the perfect setting to indulge in the colours and scents of our valley for a complete relaxation and comfort with breathtaking views, only 400mt far from Cortona  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

4 Nights min stay

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from £300 /night

£2100 - £3700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £97 /night

£678 - £721 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Casa Astrale is a lovely apartment providing a perfect base to explore southern Tuscany and Umbria. With its exclusive pool, very large gardens and , the ability to walk or cycle along the lake Trasimeno -  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £98 /night

£686 - £1412 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A tranquil haven in which to recharge your batteries. Poolside relaxation with cultural visits. Great hill walking at the summit of Tuscany's toughest cycling hill climb. All this from our family friendly cottage-style apartment set high above the Tiber valley. Good sightseeing and great restaurants at nearby Cortona. An hour's drive from Perugia, Arezzo and Assisi.  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

4 Nights min stay

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from £108 /night

£750 - £2218 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Casale GinezzO is beautiful independent Villa, located 15 km from Cortona, in the heart of the cortonese mountains, immersed into the green woods of oak and chestnut trees. From the big garden you can enjoy the charming and unspoilt natural environment  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £100 /night

£699 - £2199 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful 800 year-old hilltop villa with stunning views , 4 bedrooms (sleeps 10) and private 12m x 6m pool. On border of Tuscany and Umbria, perfect for exploring local area. Fully restored, the house exudes character. ideal for large groups and families.  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £64 /night

£444 - £621 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • 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

14 Photos

Villa | 7 Bedrooms | sleeps 24

Excellent 5/5 

3 Nights min stay

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from £53 /night

£371 / week

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Key info:

  • Nearest beach 250 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Nobile is a stunning 19th Century classical villa recently restored farmhouse 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. Private, Tranquil, Perfect for large get togethers or for small families. Perfect for Children of all ages  …see more

22 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

1 night min stay

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from £242 /night

£1694 - £2259 / week

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Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a old village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome. 30 minutes from the highway and 10 from the train station.  …see more

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1371 - £2783 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This charming Tuscan Farmhouse with a new salt water pool is ideal for family holidays as it is tucked away in a large garden in lovely, unspoilt Southern Tuscany near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £104 /night

£726 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming villa with private pool near Cortona and lake Trasimeno  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

7 Nights min stay

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from £167 /night

£1166 - £2279 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
For those who enjoy privacy, this beautifully restored traditional Tuscan farm house offers the opportunity experience real Tuscan living.  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 7

Excellent 5/5 

7 Nights min stay

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from £220 /night

£1534 - £2156 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This is a place to enjoy an authentic Tuscan experience. Close to the historic town of Cortona and set in acres of olives and pastures - this beautiful 17th century newly renovated Mill House with private pool has been painstakingly restored.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £287 /night

£2009 - £2380 / week

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Key info:

  • Nearest beach 26 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The Villa is set along a sun soaked hill where the garden extends into pretty olive groves and vineyards.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £135 /night

£944 - £2936 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Characteristic farmhouse near Cortona in Tuscany immersed in large private gardens, situated at the foot of the ancient town of Cortona.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

Good 3/5 

4 Nights min stay

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from £132 /night

£924 - £1730 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Gloria is a quaint cottage that is set in a charming and panoramic position, with completely authentic surroundings. Immersed in the lush mountains of Cortona, near the border between Tuscany and Umbria  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £329 /night

£2300 - £4145 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Lovingly restored in 2004 Villa Orlando sleeps 8 people comfortably with four bedrooms, all with en-suite bathrooms with showers. This villa is perfect for families or groups that like to spend time enjoying the outdoors.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £493 /night

£3445 - £4550 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden

Cortona Tuscan Villa with pool- rural views and two independent annexes within walking distance of the medieval walled town of Cortona.

 …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £173 /night

£1210 - £2178 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Beautiful, recently renovated villa Del Calcinaio with private pool and panoramic views from Cortona in Italy. Look at casasud.nl and book!  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 12

4 Nights min stay

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from £300 /night

£2100 - £3954 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Torre degli Elci is set in the greens of the Tuscan countryside, midst olives and cypress trees and just 4 km from Cortona. The name of the Villa derives from the old sighting tower which has testimonials from 13th and 14th century and which became a monastery  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 17

4 Nights min stay

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from £461 /night

£3226 - £4033 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The property Villa il Trebbio is an antique palace close to Cortona which dates back to the 16th century. The farmhouse in stone has been personally furnished by the owner with antique family pieces and reflects a simple and at the same time elegant atmosphere  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £217 /night

£1513 - £2380 / week

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Key info:

  • Nearest beach 135 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on a hillside and surrounded by the vineyards of a famous local wine producing farm, Villa Al Pozzo is the ideal place to spend a holiday in complete relaxation and tranquility. Independent villa of about 400 square meters that can accommodate up to 12 people.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £248 /night

£1730 - £3343 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Liliana is perfectly situated to enjoy the spectacular views of our beautiful valley. Villa Liliana sleeps up to 10 people.  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £572 /night

£4000 - £6775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Restored to high standard. Accommodation split in two private buildings. Ideal location between South Tuscany and Umbria. Private tennis court.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £248 /night

£1730 - £3343 / week

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Key info:

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

18 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £132 /night

£924 - £2380 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
The property is situated on the hills which surround Cortona. It's a characteristic villa in rustic style which develops on two independent levels, each equipped with kitchen and comforts.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 15

7 Nights min stay

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from £169 /night

£1177 - £2452 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This secluded Cortona farmhouse for 15 people is perfect for families and friends. Situated in the Tuscan province of Arezzo, this villa boasts a magnificent swimming pool.  …see more

19 Photos

Villa | 9 Bedrooms | sleeps 18

4 Nights min stay

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from £340 /night

£2380 - £3460 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
A holiday farm for a different holiday experience in untouched nature and relaxation. The Palazzo is an enchanting late 19th century country building recently fully renovated and restored, returning to its ancient splendour through accurate work, divided in 6 apartments  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 14

4 Nights min stay

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from £152 /night

£1061 - £1670 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Casa Delia is an antique villa which lies at the bottom of a green hill of Cortona in a quiet and panoramic position. The villa is surrounded by a big park, partly shaded by trees, and with its beautiful swimming pool looks onto the Chiana valley and Cortona  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

4 Nights min stay

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from £182 /night

£1271 - £2884 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa le Corchie is a charming villa located in a quiet and panoramic position in one of the most scenic areas of the hills surrounding Cortona.  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £141 /night

£981 - £1613 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

4 Nights min stay

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from £133 /night

£928 - £2073 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Maria Laura rises in panoramic position, dipped in the green and tranquility of the cortonesian hills, ideal for all of those who wish to enjoy the beauty and tranquility which this place can offer.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £100 /night

£694 - £1327 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
This charming independent villa is situated in panoramic position in the Cortonese Mountains above the Etruscan hill town of Cortona. It's ideal location make it easy visit the most renowned historical and art cities of Tuscany and Umbria.  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £108 /night

£750 - £1593 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
La Farnetina is a charming independent Villa, part of a big property dating back to the first years of the 20th century, located in a beautiful position in the countryside around Cortona, at only 14 Km from the historical centre.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £100 /night

£694 - £1412 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Nice property comprising several stone buildings situated in panoramic location on the hills around Cortona, at 750 m above-sea-level. This property is surrounded by beautiful woods and valleys and offers extensive views.  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £108 /night

£750 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Il Biancospino is a gracious property ideal for families and small groups, immersed in the greens of the cortonese mountains between oak and chestnut trees.  …see more

14 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £160 /night

£1120 - £1600 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Pets welcome
  • Private garden

Tucked away in the blissful rolling countryside on the edge of Cortona, this stone cottage with its private pool is a delightful hideaway for a coupleseeking to experience the best of Tuscany and Umbria.

 …see more

16 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £939 /night

£6570 - £9899 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
A stunning completely renovated Tuscan farmhouse. The central stone building of the property dates back to the beginning of 1600, while the following sections were developed towards the end of 1800. It enjoys spectacular views across the Tuscan countryside  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 12

4 Nights min stay

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from £104 /night

£726 - £1613 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
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  …see more

22 Photos

Villa | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £195 /night

£1363 - £1678 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Stunning villa in an extremely panoramic position in the vicinity of Cortona.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £190 /night

£1329 - £2363 / week

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Key info:

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

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £124 /night

£863 - £1510 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £140 /night

£978 - £2200 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 10  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £88 /night

£612 - £1067 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £152 /night

£1061 - £1625 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 4  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £126 /night

£880 - £1589 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 9  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £58 /night

£404 - £856 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 4  …see more

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