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127 Holiday homes in Cortona

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127 Results  |  
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

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

16 Photos

Apartment | 1 Bedroom | sleeps 2

Very Good 4.5/5 

5 Nights min stay

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from £50 /night

£350 / week

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Key info:

  • Nearest beach 7 km
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
Fifteen minutes walk to Cortona on a private path with exceptional views, the stone-house is secluded, and restored and furnished with taste. Surrounded by garden terraces on various levels, and well provided with garden furniture for outdoor meals and relaxation. SEPTEMBER OFFER: £250 for 5 or 7 nights. Gourmet-meals under request.  …see more

Featured properties

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

22 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £61 /night

£426 - £608 / week

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Key info:

  • Nearest beach 165 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
The apartment Angelo is part of a larger building once an ancient mill which has been carefully restored to the highest standards and transformed into a country residence with 30 apartments enjoying stunning views, immersed in a green setting only 3 km from Cortona.  …see more

24 Photos

Apartment | 4 Bedrooms | sleeps 6

2 Nights min stay

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from £80 /night

£556 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Great for children of all ages
  • 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

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
  • 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
  • Car not necessary
  • No pets allowed
  • Private garden
cortona farmhouse agriturismo  …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

21 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4/5 

2 Nights min stay

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from £103 /night

£716 - £836 / week

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Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Il Bozzino, a lovely ancient Tuscan farmhouse, with swimming pool, just minutes from Cortona, beautiful medieval Tuscan town. Join the peace and traquillity of the tuscan country with the convenience of the close main roads and railroads to visit Tuscany end Umbria Azienda Fontelunga has some of the most appealing villas of the Cortona area available for rental.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

2 Nights min stay

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from £48 /night

£334 - £389 / 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
Seni detached apartment of an ancient tuscan country house, private garden in a small country village near by Corotna, the famous meieval town. Swimming pool and traditional tuscan food lessons available  …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

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

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

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

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

12 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £67 /night

£468 - £565 / 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
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

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 | 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

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
  • 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

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

13 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

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
  • 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

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
  • 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

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

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1371 - £2783 / week

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Key info:

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

10 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £52 /night

£363 - £638 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great 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

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
  • 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

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

22 Photos

Villa | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £195 /night

£1363 - £2097 / week

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Key info:

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

20 Photos

Villa | 8 Bedrooms | sleeps 17

7 Nights min stay

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from £461 /night

£3226 - £4033 / week

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Key info:

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

20 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £231 /night

£1613 - £2307 / 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
Amidst the olive trees that surround the walls of the ancient city of Cortona, lies Villa Olea, a delightful recently restored property, ideal for all who search privacy and tranquility.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £248 /night

£1730 - £3113 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Above the wood oven is engraved 1781. Villa Nello was restored in 2001. It develops on three floors, sleeping 8 people, plus a small independent single bedroom with bathroom.  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 17

4 Nights min stay

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from £271 /night

£1896 - £3460 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
La Colombaia is a leopoldine house, typical residence of the 16th century of the Val di Chiana, finely restored respecting the material and original architectonic characteristics.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

4 Nights min stay

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from £182 /night

£1271 - £2307 / week

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Key info:

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

18 Photos

Villa | 4 Bedrooms | sleeps 12

4 Nights min stay

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from £108 /night

£750 - £1613 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Neri is situated in San Lorenzo in close driving proximity to Cortona. Cortona is an antique Etruscan town which lies in the heart of the Chiana valley. You can even see the town perched on the hill in front of you  …see more

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

16 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £133 /night

£928 - £2073 / week

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Key info:

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

18 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £132 /night

£924 - £2192 / week

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Key info:

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

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

18 Photos

Villa | 6 Bedrooms | sleeps 14

4 Nights min stay

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from £165 /night

£1154 - £2017 / week

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Key info:

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

16 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £100 /night

£694 - £1271 / week

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Key info:

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

13 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £108 /night

£750 - £1593 / week

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Key info:

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

18 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

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
  • 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

16 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £141 /night

£981 - £1613 / week

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Key info:

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

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £248 /night

£1730 - £3226 / week

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Key info:

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

6 Photos

Guest house | 6 Bedrooms | sleeps 25

1 night min stay

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from £79 /night

£548 - £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
  • Private garden
La Fiorita is a farmhouse nestled in the beautiful Tuscan countryside, on the border between the provinces of Arezzo and Siena.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £61 /night

£424 - £594 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
A magnificent suite for 4 persons on the basis of the first floor. 4 designed in the 1800s style. sleeps 4 people. 2 bathrooms, 2 master bedrooms, very spacious living room with fireplace, large kitchen next to the terrace. Many cozy corners to relax inside or outside. Large private terrace with dining table and chairs, invisible to all the other guests with.  …see more

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Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £69 /night

£479 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa La Fontana is at the heart of prestigious places of historical interest and artistic national and world: ROME, the capital city with all its historical and architectural merit is about u'ora machine, FLORENCE, capital of the Renaissance is about an hour's journey. CORTONA is located just 15 minutes, ORVIETO 30 minutes, 40 min. SIENA, PERUGIA 20 min., Assisi 30 min.  …see more