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308 Holiday homes in Cortona

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308 Results  |  
20 Photos

Villa | 13 Bedrooms | sleeps 30

Excellent 5/5 

3 Nights min stay

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from £86 /night

£599 - £9652 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Medieval stone farmhouse renovated and divided to 9 charming luxurious suites that can accommodate one double bedroom and 2 double bedrooms suites, in full comfort in authentic Tuscan farmhouse furnished and kept with the old world style. Ideal for day trips. Hometuscany Tours & accommodation has an objective to provide the highest quality of accommodation  …see more

17 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £163 /night

£1137 - £1240 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
La Mucchia Casa Vacanza & Art Gallery is located in the Tuscany region in the best location for day trips and short excursions for short drives. The villa in Cortona is situated at the foot of the hills around the Cortonese Valey, called Valdichiana. The best location for day trips to visit many cities in Tuscany within one hour drive  …see more

17 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £171 /night

£1197 - £1454 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Chosen by hundreds of guests on Tripadvisor as number one Medieval Farmhouses in Cortona, we were awarded since 2010 every year with certificate of excellency. The area also provides various facilities for outdoor activities, quad,bikes,horses,golf,tennis and more  …see more

Featured properties

21 Photos

Farmhouse | 1 Bedroom | sleeps 3

3 Nights min stay

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from £111 /night

£774 - £881 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
La Mucchia Casa Vacanza & Art Gallery is located in the Tuscany region in the best location for day trips and short excursions for short drives. The villa in Cortona is situated at the foot of the hills around the Cortonese Valey, called Valdichiana. “La Mucchia casa vacanza & art gallery”, being one of the most luxurious vacation villas in Tuscany  …see more

20 Photos

Hotel apartment | 1 Bedroom | sleeps 2

6 Nights min stay

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from £104 /night

£727 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
We are located in the best point for day trips, you can visit many cities around within an hour drive, our apartment hotel is an medieval farm build 300 years ago and turned to luxurious apartments with all the comforts, still kept its original old world style.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

Short stays welcome

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from £110 /night

£770 - £1029 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
A former outbuilding of an old Tuscan villa, Poggiobello is a masterpiece of traditional rural architecture with high quality accommodation, extremely welcoming, tastefully furnished in the typically Tuscan style.  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

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from £81 /night

£565 - £753 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
The villa "Meridiana" is very easy to reach, is settled in the quiet Brolio Tuscany village Villa with private garden and private swimming pool Tennis table in garden. Fenced private garden. Ground floor 2-3 days a week stays the owner in order to take care to the garden and swimming pool.  …see more

21 Photos

Farmhouse | 3 Bedrooms | sleeps 7

Excellent 5/5 

7 Nights min stay

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from £139 /night

£968 - £1613 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Charming country house with private pool to rent at 1 mile from Cortona – sleeps 6+1 From 1200€ to 1800€ a week  …see more

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

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from £135 /night

£941 - £1283 / 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

7 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

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from £49 /night

£342 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
the property is settled in an ancient courtyard, perfectly renewed and keeped, with flowers and wonderful grass area. perfect for children who can enjoy outside activities. Cortona is a very famous and tipycal Italian medieval town where enjoy italian quiet life.  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £136 /night

£950 - £1090 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
This unpretentious, large house has the authentic flavour of times past and glorious views up to Cortona. The pool was built in 2008 with safety in mind: it's 3 ft 9 ins deep and completely fenced for total peace of mind.  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 5

Very Good 4.5/5 

7 Nights min stay

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from £85 /night

£590 - £790 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
700 years ago, San Silvestro was a little church - now it's a charming rental villa and excellent value too!  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £185 /night

£1291 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful property carefully and completely renovated in the heart of the Chiana Valley just 9 km from the beautiful town of Cortona.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £358 /night

£2500 - £3210 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
With a history dating back to the 17th century, this recently renovated villa distinguishes itself not only by its traditional architectural features and elegant antique furnishings, but above all by its unequalled setting.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £404 /night

£2823 - £5646 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Magnifica is an old country residence, skilfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1372 - £1847 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Le Contesse sleeps 6+2 people in three bedrooms with three bathrooms and another four people in two annexes (Serenella & Limonaia), each with it's own living room, kitchenette bathroom and bedroom.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £335 /night

£2339 - £4194 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Fonte is located in an extraordinary panoramic position in the open countryside surrounded by olive trees and other typical Tuscan plants but within walking distance from the famous historical town of Cortona just 400 meters away.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £133 /night

£925 - £1970 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
This imposing two-storey villa is set in stunning grounds, which have the quality of a park. Here you can feel sheltered and secluded in each separate area, including that of the pool.  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 6

1 night min stay

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from £77 /night

£539 - £843 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
La Fiorita is a farmhouse nestled in the beautiful Tuscan countryside. From every corner of the estate you have magnificent views of bucolic flavor with wide open spaces overlooking the hills of Montepulciano and Cortona  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £132 /night

£924 - £1667 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
cortona farmhouse agriturismo  …see more

11 Photos

Apartment | 4 Bedrooms | sleeps 5

2 Nights min stay

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from £80 /night

£556 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
Welcome to “Casale il Granaio”, a magic place in the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno lake and in the middle between the cities of Arezzo and Perugia. From here is easy also to reach Montepulciano, Siena, Pienza, Rapolano and Spoleto.  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £123 /night

£855 - £1069 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

13 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £80 /night

£557 - £670 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • 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

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 5
  • 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

11 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £172 /night

£1202 - £1331 / week

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Key info:

  • Nearest beach 25 km
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

16 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £80 /night

£557 - £1025 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

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 5
  • 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

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 5
  • 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

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 5
  • 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

22 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £133 /night

£928 - £1315 / week

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Key info:

  • Nearest beach 28 km
  • Swimming pool
  • Great for children of all ages 5
  • 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 | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £139 /night

£968 - £1737 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £93 /night

£649 - £2199 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

20 Photos

Villa | 5 Bedrooms | sleeps 15

5 Nights min stay

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from £289 /night

£2017 - £2823 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Luxurious detached villa with private pool in southern Tuscany near Cortona. Panoramic and quiet location. 5 bedrooms, 11 bed places + 2 double sofa beds. Air conditioning and Wi-fi internet connection.  …see more

14 Photos

Villa | 7 Bedrooms | sleeps 24

3 Nights min stay

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from £57 /night

£394 - £2475 / week

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Key info:

  • Nearest beach 250 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

10 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £62 /night

£428 - £513 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Holiday apartment 2 km from Cortona in the country, equipped with every comfort ,silent An excellent base for excursions nearby (Lake Trasimeno, Montepulciano, Pienza, Siena, Gubbio, etc..), from the house you can also put your shoes on and go for a walk in the woods  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £110 /night

£764 - £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

19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £37 /night

£257 - £684 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
The apartment Sant'Angelo is located just below the Etruscan City of Cortona in a beautiful residential complex which has been tastefully restored, maintaining the traditional characteristics of the antique oil mill that it once was. Video footage of apartment on Youtube is available on:http://youtu.be/wR2cgZSvDOM  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £49 /night

£342 - £513 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
From the town of Cortona and 'possible in the day, to reach the most beautiful art cities of central Italy from Florence to Rome and 18 km Lake Trasimeno.Included you will find a set that includes: basic necessities (coffee, tea, seasoning, salt, sugar, detergents...... Ideally located, very quiet. Discount depending on length of stay.completely renovated, nice furnishings.  …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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Late Deal: save up to €849 (approx. £685)

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

7 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £742 /night

£5194 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Private Villa in Cortona Area, Near Montepulciano, Tuscany, Italy. Private Swimming Pool, sleeps 18. Beautiful gardens, green grass all year. Multiple family accommodation. Broadband, TV, DVD, iPod docks, table-tennis, bikes.  …see more

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £208 /night

£1454 - £1696 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
The location is vry convenient to visit many of the most beautiful location of central Italy, Tuscany and Umbria, still stayng in a relaxing and peaceful country place.Cortona, the awesom art city, made famous also from teh movie "under the Tuscan Sun" is very close  …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
  • Great for children of all ages 5
  • 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

14 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £71 /night

£495 - £750 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £49 /night

£339 - £525 / week

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Key info:

  • Great for children of all ages 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Stunning breath taking view of the Val di Chiana Valley from the living room and kitchen windows!! It'll be printed in your memory for ever! Walking distance from the main square and all the fabulous restaurants and shops.  …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 5
  • Car essential
  • Pets welcome
  • Private garden
Charming villa with private pool near Cortona and lake Trasimeno  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £209 /night

£1462 - £2167 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
This typical Tuscan-styled agritourism farmhouse is charming and dates back to the 15th century. It is located in one of the most beautiful hamlets of Italy, Preggio, which is near Cortona.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £289 /night

£2017 - £3025 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
This beautiful 5 bedroom villa enjoys a privileged elevated location. The villa is surrounded by woodland with impressive views of Valdichiana and even Lake Trasimeno.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £375 /night

£2621 - £3831 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Noce is split on two levels, with the ground floor offering a large living and dining room. The interior is an authentically rustic affair, with the antique furniture in keeping with the traditional feel of the outside space.  …see more

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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 couple seeking to experience the best of Tuscany and Umbria.

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20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £153 /night

£1069 - £1283 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Family- friendly 3 bedroom restored Farmhouse with private pool, just below Cortona  …see more