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137 Holiday homes in Cortona

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137 Results  |  
19 Photos

Villa | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £237 /night

£1654 - £1993 / week

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Key info:

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

24 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £338 /night

£2362 - £3634 / 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

24 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4.5/5 

7 Nights min stay

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from £184 /night

£1283 - £2565 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Le Celle del Farinaio is a villa for about 12/14 people. The property, completely fenced, is' situated on a hill (350 meters),  …see more

Featured properties

23 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £159 /night

£1112 - £2138 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The house is ideal for a relaxing, comfortable and romantic. An old farmhouse dating back to 1200 recently renovated very close to monuments, delicious restarants, all the comfort s for your relax  …see more

18 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £59 /night

£411 - £770 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
relax, old tuscany charming, comfort, beautiful overview. perfect for your vacation the cities of Siena, Florence and Perugia are easily reached in less than 1 hour driving  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 15

Short stays welcome

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from £364 /night

£2544 / 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

23 Photos

Villa | 2 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

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from £74 /night

£513 - £855 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Swimming pool, beach or lakeside relaxation, air conditioning, car essential, may take pets - please enquire, Cortona, panoramic  …see more

23 Photos

Villa | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £49 /night

£342 - £727 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Swimming pool, beach or lakeside relaxation, air conditioning, car necessary, may take pets - please enquire, Cortona,  …see more

11 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

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from £273 /night

£1908 - £3790 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Fonte Vecchia is Situated Deep in the Heart of Piero della Francesca Country in the Niccone Valley and is rated one of the top 15 villas to stay in Italy  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £93 /night

£651 - £1069 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The Orangery, charming villa with private swimming pool is placed in the magnificent Tuscan countryside, surrounded by olive trees and vineyard: the perfect setting in an atmosphere of complete relaxation and comfort but also only 400 mt far from the stunning Cortona  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £158 /night

£1103 - £1287 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
3 bedrooms Tuscan country villa in panoramic location with private swimming pool , private garden and parking . Five minutes away from the beautiful medieval city of Cortona and the famous cooking school I Gustasapori  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

1 night min stay

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from £38 /night

£265 - £2138 / week

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Key info:

  • Nearest beach 150 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Giarradea is the perfect choice for all the people want to spend a beautiful vacancy completely immersed in the peace of the Tuscan nature, without give up to the comfort. The Villa is really near to beautiful trekking, but at just 10 minutes by car from Cortona  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

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from £334 /night

£2332 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Martino offers not just another holiday in Tuscany or Umbria; this is a really special place. The villa is beautifully presented and has an exquisite pool with spectacular views across the famous Niccone Valley towards Mercatale di Cortona. Only 15 minutes from the villa you can easily access the Etruscan town of Cortona.  …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
  • 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

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
  • 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

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
  • 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

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
  • 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
  • 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

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
  • 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

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
  • 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

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
  • 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 | 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
  • 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

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
  • 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

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
  • 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

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

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
  • 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 £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

21 Photos

Villa | 1 Bedroom | sleeps 2

Excellent 5/5 

7 Nights min stay

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from £115 /night

£805 - £1059 / week

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Key info:

  • Nearest beach 14 km
  • Great 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

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
  • 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

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
  • 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

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

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
  • 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £298 /night

£2085 - £2565 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A typical Tuscan house in bricks, with a garden, fruit trees, flowering trees, cypresses and rosemary bushes, a beautiful swimming pool is in the centre of the garden  …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
  • 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

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
  • 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 | 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
  • 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
  • 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

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
  • 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

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
  • 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

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
  • 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

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
  • 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

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
  • Pets welcome
  • Private garden
Charming villa with private pool near Cortona and lake Trasimeno  …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

11 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £98 /night

£684 - £1266 / 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
This lovely small villa is located at 400 m from the charming town of Cortona It is situated in a wonderful panoramic position, surrounded by the typical Tuscan countryside and olive groves, in a perfect location for a lovely and relaxing holiday, yet with the advanta  …see more

9 Photos

Villa | 6 Bedrooms | sleeps 15

7 Nights min stay

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from £420 /night

£2936 - £4421 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This incredible structure offers to its guests two different accommodations completely independent : the Villa and the cottage.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £379 /night

£2650 - £4189 / 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £336 /night

£2351 - £3463 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Stunning Luxury villa in walking distance from Cortona, the famous and well know medieval village thanks to the "under the Tuscan sun" book and movie.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £100 /night

£694 - £928 / 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

16 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £105 /night

£734 - £1311 / week

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Key info:

  • Nearest beach 35 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Splendid Tuscany cottage in a picturesque and peaceful spot in the mountains above Cortona.  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £108 /night

£750 - £1734 / 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