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332 Holiday homes in Cortona

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332 Results  |  
12 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £95 /night

£662 - £1240 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Casa Patrizia is a typical holiday house. The villa has a completely independent apartment on the ground floor with two entrances, with private garden, veranda with table and chairs, elegantly furnished and decorated in typical Tuscan style.  …see more

15 Photos

Farmhouse | 4 Bedrooms | sleeps 8

Short stays welcome

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from £91 /night

£637 - £1323 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Old 13th century farmhouse furnished in style and surrounded by the Tuscan hills at just Km from Cortona and Lake Trasimeno. The property is divided in 4 bedrooms, 2 bathrooms, 2 living rooms, kitchen, and pantry.There is a swimming pool with panoramic terrace.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £94 /night

£653 - £976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
In the surroundings of Cortona, one of the most wonderful cities of art in Tuscany, lies the Agriturismo Isolina, deep in the green hills of the valley Valdichiana.  …see more

Featured properties

9 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £57 /night

£397 - £910 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
The il Borgo Agritourism Complex is near the historic Etruscan city of Cortona. It is in a beautiful country setting amongst olive trees, cypresses and sunflowers in the Chiana Valley.  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £89 /night

£620 - £1034 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Independent stone house at the foot of Cortona with swimming pool, garden  …see more

8 Photos

House | 2 Bedrooms | sleeps 5

Min stay varies

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from £60 /night

£414 - £579 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
3-room semi-detached house 100 m2 on 1st floor, spacious, comfortable furnishings: living room with 1 sofa bed, open fireplace and satellite-TV. Exit to the loggia.  …see more

17 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £57 /night

£397 - £703 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Dive in the pool of our rental house in Tuscany. A villa for your luxury vacation. Beautiful medieval stone hamlet situated in quiet and panoramic position between olive trees and woods of ancient chestnut trees, typical of Tuscany.  …see more

21 Photos

Apartment | 3 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £95 /night

£662 - £1447 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
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

19 Photos

Farmhouse | 3 Bedrooms | sleeps 9

3 Nights min stay

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from £100 /night

£695 - £1695 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Dardano is a simple but charming 3 bedroom farmhouse sleeping up to 9 people. Outside guests enjoy a private garden and private swimming pool (open from mid May to the end of September each year). Inside it is furnished simply but tastefully in a traditional Tuscan style.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 13

3 Nights min stay

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from £257 /night

£1795 - £2995 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This is a beautiful 6 bedroom converted farmhouse which was newly renovated in 2010. Set in extensive grounds it is an incredibly peaceful location, with rolling lawns surrounded by woods and olive trees. The Tuscany villas is ideally placed for sightseeing, close to Cortona, and within easy reach of Florence and Siena. Guests have use of a large private pool. WIFI. BBQ.  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £91 /night

£631 - £813 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Charming cottage near Cortona, set in 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. Rental rates are all-inclusive Free GPS, Italian cell phone,laptop. Swimming pools/thermal spas. Great restaurants. Short walk to village.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £61 /night

£421 - £675 / week

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Key info:

  • Nearest beach 149 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Old Tuscan farm-houses recently restored. No so far to Cortona, beautiful Etruscan town, is the ideal place for your next holiday; where you can look at art, nature and culture. Internet free in the garden.  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £98 /night

£686 - £825 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa August' provides a good value family holiday in Tuscany, Cortona. With its huge swimming pool, tennis court, barbecues and lots of space both inside and out, this is a perfect for young/teenage families to enjoy the area.  …see more

15 Photos

Apartment | 4 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £129 /night

£901 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This lovely apartment is available for a minimum of 4 nights. A perfect location in the heart of Cortona and, a great base to explore many of Tuscany's and Umbria's famous towns, vineyards and stunning countryside.  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £163 /night

£1141 - £1364 / week

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Key info:

  • Nearest beach 25 km
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Coppa di Sopra is an elegant and enchanting villa overlooking one of Tuscany's favorite valleys - “Coppa di Sopra is a magical place.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

7 Nights min stay

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from £171 /night

£1195 - £2335 / week

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Late Deal: save up to €801 (approx. £662)

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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 | 1 Bedroom | sleeps 2

Excellent 5/5 

7 Nights min stay

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from £118 /night

£825 - £1086 / week

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Key info:

  • Nearest beach 14 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Why have so many people fallen in love with the charm of Cortona? Although the central area of this lovely and ancient city is well known to many, there remains the secret and ever-so-charming quarter where this hidden gem will inspire and charm you.  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 7

Excellent 5/5 

7 Nights min stay

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from £225 /night

£1572 - £2210 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Suitable 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 | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £142 /night

£992 - £1695 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
exceptional, Good value. Villa Sonia ioffers a fabulous Tuscan home for two to 14 guests! Fantastic views, Private Pool, Tranquility, Relaxation and much more.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £101 /night

£703 - £820 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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

16 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £62 /night

£430 - £1050 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
"Perfect for half terms holidays - without any increase in the general rate" . Casa Serena is a really charming little house/villa is set in the middle of olive grove and surrounded Tuscan woodland, and provides privacy and serenity for a truly relaxing vacation.  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £136 /night

£951 - £1348 / week

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Key info:

  • Nearest beach 28 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
If you have a larger gathering, The estate offers two villas, this and another autonomous villa for 10 guests offers two lovely and independent stone villas. Each with its own private pool, gardens and access road.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £294 /night

£2058 - £2439 / week

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Key info:

  • Nearest beach 26 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
The Villa is set along a sun soaked hill where the garden extends into pretty olive groves and vineyards.  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £69 /night

£480 - £662 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Apartment Roland is a fun and stylish and inexpensive home set in the foothills of Cortona are two individual and lovely properties with spacious gardens, magnificent private pool, tennis court and many wonderful features.  …see more

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £163 /night

£1139 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

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

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £50 /night

£350 - £635 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Apartment with private terrace and splendid pool with jacuzzi set in gardens with shady arbours. Lovely views across the fields to the hills. Short walk to shops, bars and restaurants. Near Cortona and Lake Trasimeno. Ideal for Assisi and Perugia as well as Tuscany.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £71 /night

£495 - £1050 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
On the Tuscany / Umbria border, the old farm of Azienda Pilari is only a short drive to Cortona and Lake Trasimeno. A walk across the field takes you to an old market town with a few shops, bars and restaurants Wine and olive oil produced on the farm are available for purchase.  …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

8 Photos

Villa | 3 Bedrooms | sleeps 5

4 Nights min stay

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from £111 /night

£776 - £1267 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
5-room house, detached, for 5 people, 180 m2, simple and comfortable furnishings. Living/dining room with local TV, satellite-TV, open fireplace, dining-table and dinette. Smoking not allowed. Internet (DSL/LAN). Sleeping room with 2 single beds. Sleep  …see more

9 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £97 /night

£679 - £1194 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
4-room house, detached, for 6 people, 145 m2 on 2 levels, simple and comfortable furnishings. Living/dining room with local TV, satellite-TV, DVD, open fireplace, dining-table and dinette. Smoking not allowed. 3 double beds. Sleeping room with 1 double  …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

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

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

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

22 Photos

Farmhouse | 3 Bedrooms | sleeps 5

Short stays welcome

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from £151 /night

£1052 - £1315 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
trekking strategic point, silent, beautiful country house, stone view walls, Unfortunately is not possible to use BBQ by law during summer season because woods are too near the house...  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 14

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The villa is composed of 2 buildings. Main building: ground floor: with dining room, kitchen, bathroom and 3 bedrooms. I° floor: with dining room, kitchen, bathroom and 3 bedrooms. II° building: small house with 2 bedrooms, bathrooms, dining room, living room  …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

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

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

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

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

24 Photos

Apartment | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £207 /night

£1447 - £1852 / week

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Key info:

  • Nearest beach 180 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
These two apartments can accommodate a total of 12 guests if rented together but can also be rented individually for groups of 2-4 and up to 8 respectively. Casa Medicea is conveniently located right in the heart of Cortona near to all amenities.  …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 | 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