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249 Holiday homes in Cortona

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Filters applied: Swimming pool (249)

249 Results  |  
14 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £71 /night

£495 - £950 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
On the Tuscany/Umbria border, near Cortona and Lake Trasimeno, Castagnolo is one of 3 beautifully restored apartments. In the garden is a luxurious pool with jacuzzi attached . Walk across the field to the old market town of Mercatale. Private terrace. Wonderful views  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

Min stay varies

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from £188 /night

£1315 - £2629 / 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
Villa il Pino is an old farmhouse carefully restored while maintaining the aesthetic standards of the old Tuscan farmhouses using the original materials, such as roofing tiles, the handmade terracotta tiles for the floors, doors and windows all handcrafted in solid che  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £110 /night

£764 - £1580 / week

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Key info:

  • Nearest beach 22 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

Featured properties

24 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £107 /night

£744 - £2067 / week

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Key info:

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

10 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £54 /night

£372 - £654 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Beautifulapartment with swimming pool situated in the vicinity of Cortona, Tuscany.  …see more

16 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £154 /night

£1075 - £1819 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Farmhouse near Mercatale di Cortona, Tuscany, Italy 300 Year old stone Tuscan farmhouse with pool and panoramic views, totally renovated One of a kind luxury farmhouse, sleeps 6 adults + 2 children (3 bedrooms) An ideal location from which to explore both Tuscany and Umbria.  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £88 /night

£614 - £1271 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
La Fenice is part of a beautiful restored farmhouse, contained in private walled and hedged, landscaped gardens. Romantic, family and site seeing, all are catered for, plus use of the magnificent 20mX 8m swimming pool. makes an ideal holiday location for everyone. Part of the privately owned I Casali di Montecchio, there are wonderful views of Cortona from the garden.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £139 /night

£967 - £3009 / week

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Key info:

  • Swimming pool
  • Suitable 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

10 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £108 /night

£753 - £1505 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Delightful rustic cottage with beamed ceilings, situated in an idyllic spot in the mountains above Cortona, just 14 minutes from the town.  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 11

1 night min stay

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from £123 /night

£860 - £2042 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Typical Tuscan country house in a beautiful woodland setting in the hills above Cortona, on the border between Tuscany and Umbria.  …see more

8 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £81 /night

£562 - £819 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Charming Tuscany villa rental set in the parkland of an aristocratic villa which dates back to 1773 situated at the foot of the ancient Town of Cortona.  …see more

15 Photos

Villa | 6 Bedrooms | sleeps 12

Min stay varies

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from £237 /night

£1653 - £2934 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Immersed in the hills surrounding Cortona at just 16 km from the centre, Villa Grazia offers a peaceful relaxing holiday in the midst of secular oak and chestnut trees.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 16

Min stay varies

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from £300 /night

£2100 - £3700 / 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 Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 12

Min stay varies

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from £354 /night

£2475 - £3765 / week

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Key info:

  • Swimming pool
  • Suitable 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

14 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

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from £110 /night

£769 - £2067 / week

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Key info:

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

16 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £102 /night

£711 - £1302 / week

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Key info:

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

20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £182 /night

£1273 - £2720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This traditional villa in Cortona for 14 people is perfect for a large group of friends. The accommodation offers a swimming pool and a pet-friendly space.  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

7 Nights min stay

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from £296 /night

£2067 - £3100 / week

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Key info:

  • Swimming pool
  • Suitable 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

18 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £307 /night

£2145 - £3860 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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 | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £54 /night

£372 - £802 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This property in Tuscany Italy is a stunning villa that sleeps 4 people, so it is ideal for small families. The accommodation offers a swimming pool and air conditioning.  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £63 /night

£435 - £736 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 6 persons, with swimming pool , in Cortona  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £159 /night

£1113 - £1704 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Holiday house for 4 persons, with swimming pool , in Cortona  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £64 /night

£446 - £666 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 6 persons, with swimming pool , in Cortona  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £56 /night

£388 - £684 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Holiday house for 6 persons in Cortona  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £47 /night

£325 - £539 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 2 persons, with swimming pool , in Cortona  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £82 /night

£568 - £985 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 5 persons, with swimming pool , in Cortona  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 12

4 Nights min stay

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from £107 /night

£744 - £1653 / week

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Key info:

  • Swimming pool
  • Suitable 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

17 Photos

Villa | 6 Bedrooms | sleeps 12

Min stay varies

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from £287 /night

£2003 - £2940 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
This charming old villa inserted in the enchanting setting of the typical chiana valley Tuscan landscape, Villa Salcotto lies at the foot of the hill of Cortona, a delightful town whose Etruscan origins left it with a still very conspicuous archaeological heritage  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 14

7 Nights min stay

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from £165 /night

£1153 - £1922 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Holiday house for 14 persons, with swimming pool , in Cortona  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £102 /night

£711 - £1302 / week

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Key info:

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

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £254 /night

£1773 - £3306 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

House | 3 Bedrooms | sleeps 7

1 night min stay

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from £60 /night

£414 - £827 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

21 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £74 /night

£516 - £941 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Cortona  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £119 /night

£827 - £1653 / 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 is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £60 /night

£414 - £744 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

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

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £506 /night

£3540 - £4685 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
CoCortona Tuscan Villa with pool- rural views and two independent annexes within walking distance of the medieval walled town of Cortona.  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 17

7 Nights min stay

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from £473 /night

£3306 - £4133 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

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

24 Photos

Villa | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £169 /night

£1182 - £1962 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
Holiday house for 8 persons, with swimming pool , in Cortona  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £134 /night

£933 - £1681 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Holiday house for 9 persons, with swimming pool , in Cortona  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £52 /night

£360 - £744 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

18 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £130 /night

£910 - £1733 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Holiday house for 9 persons, with swimming pool , in Cortona  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £136 /night

£947 - £2246 / 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 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

20 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £136 /night

£947 - £1773 / 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 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

20 Photos

House | 3 Bedrooms | sleeps 7

1 night min stay

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from £69 /night

£480 - £951 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

11 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £131 /night

£916 - £1599 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Holiday house for 6 persons, with swimming pool , in Cortona  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

4 Nights min stay

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from £136 /night

£951 - £2124 / 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 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

20 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £58 /night

£400 - £672 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Cortona  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £64 /night

£446 - £666 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 6 persons, with swimming pool , in Cortona  …see more