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396 Holiday homes in Cortona

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396 Results  |  
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

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

1 night min stay

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from £38 /night

£265 - £1796 / 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

22 Photos

Villa | 4 Bedrooms | sleeps 6

6 Nights min stay

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from £81 /night

£565 - £941 / 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

Featured properties

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £74 /night

£513 - £599 / week

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Key info:

  • Not suitable for children
  • No pets allowed
A weeks vacation in the town of Cortona is perfect... Enjoy the many restaurants , art galleries, shops, coffee bars and wine shops. Sit on the palace to watch the world go by. Take a walk thru the many twisting turning streets and imagine your self living here. Take a walk thru the park and around the Tuscan walls and pass Bramasole Under The Tuscan Sun  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 12

3 Nights min stay

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from £140 /night

£979 - £1834 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Vivete un'esperienza a contatto con la natura ma con tutti i confort della vita moderna.  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £159 /night

£1112 - £1625 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa indipendente in mezzo ad una secolare oliveta, ad 1 chilometro circa dalla città di Cortona, set del famoso film Under Tuscan Sun girato a circa 300 metri dalla nostra casa. 8 posti letto, ampio giardino attrezzato, piscina esclusiva, parcheggio all'interno. Possibilità di aria condizionata a richiesta  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 15

Short stays welcome

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from £364 /night

£2544 - £3074 / 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

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

14 Photos

Villa | 7 Bedrooms | sleeps 24

Excellent 5/5 

3 Nights min stay

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from £53 /night

£371 - £2335 / 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

30 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
  • 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

10 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £214 /night

£1496 / week

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Key info:

  • Not suitable for children
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Per trascorrere la tua vacanza con stile, nelle meravigliose colline toscane, questa proprietà offre 2 camere da letto e ogni servizio che può rendere unico il soggiorno. I principali servizi a pagamento sono: personal chef service, chauffeur service.  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £274 /night

£1915 / week

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Key info:

  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
Loft esclusivo, situato nel centro storico di Cortona. Il lusso e la cura dei dettagli offerti, faranno vivere la vacanza in completo relax.  …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
  • 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

24 Photos

House | 3 Bedrooms | sleeps 8

1 night min stay

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from £86 /night

£599 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Struttura ideale per una vacanza nella terra degli etruschi e per chi ama la campagna e contemporaneamente le città d'arte.  …see more

24 Photos

Studio | sleeps 2

2 Nights min stay

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from £50 /night

£350 - £436 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Casale Il Granaio is in a evocative hamlet in the countryside, in the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno Lake. The former Tavern of the property is nowadays a studio-flat offering exposed-beam ceilings and wooden furnishings, suitable for  …see more

24 Photos

Apartment | 4 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £62 /night

£428 - £544 / 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

22 Photos

Farmhouse | 3 Bedrooms | sleeps 5

Short stays welcome

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from £86 /night

£599 - £770 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • 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

21 Photos

Farmhouse | 3 Bedrooms | sleeps 7

Excellent 5/5 

7 Nights min stay

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from £139 /night

£968 - £1573 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
  • Great for children of all ages
  • 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 1950€ a week  …see more

14 Photos

Farmhouse | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £53 /night

£368 / week

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Key info:

  • Nearest beach 10 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
I 2 appartamenti, Magnolia e Mimosa, sono l' ideale per famiglie e gruppi di amici, ideale come punto di partenza per visitare, a breve distanza, splendidi luoghi e città come: Cortona, Lago Trasimeno, Arezzo, Perugia, Assisi, Siena,Val d'orcia. tutti i servizi vicini Giardino relax ombreggiato attrezzato per giochi all'aperto (ping pong, freccette, casetta per bambini)  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £67 /night

£466 - £1013 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
During the day besides going for a swim in the pool, basking in the sun and reading a good book in the shade of a nearby grove, you will be able to take a tour of a our farm consisting of woods, tilled land, lawns, ponds, olive groves, vineyards, vegetable gardens, orchards, a chicken farm and a small flock of sheep.  …see more

24 Photos

Townhouse | 1 Bedroom | sleeps 2

Excellent 5/5 

1 night min stay

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from £46 /night

£317 - £411 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Vista unica sulla valle walking distance to the historic center, sulle mura etrusche arredamento raffinato e con materiali pregiati legati alla toscana. Silenzio e relax, cultura, divertimento, buona cucina, wine & food, eventi, musei arte natura green, lago trasimeno Apri la porta ed entra in un sogno romantico: Casa Mia a Cortona ti aspetta per le tue vacanze da ricordare  …see more

14 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £147 /night

£1026 - £1496 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
IL CASALE DI CARMINA is the place for those who love nature and tranquility of the Tuscan hills.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £67 /night

£466 - £1013 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
During the day besides going for a swim in the pool, basking in the sun and reading a good book in the shade of a nearby grove, you will be able to take a tour of a our farm consisting of woods, tilled land, lawns, ponds, olive groves, vineyards, vegetable gardens, orchards, a chicken farm and a small flock of sheep.  …see more

22 Photos

B&B | 1 Bedroom | sleeps 3

1 night min stay

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from £62 /night

£428 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
Pace, confort, storia ed enogastronomia.  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £53 /night

£368 / week

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Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
E' l'ideale come punto di partenza per visitare, a breve distanza, splendidi luoghi e città come: Lago Trasimeno, Arezzo, Perugia, Assisi, Siena,Val d'orcia, ecc.. Cortona famosa Città di storia, è molto vivace e propone sempre un nutrito cartellone di eventi. Dalla nostra struttura è possibile intraprendere passeggiate nei percorsi all'interno del parco archeologico  …see more

18 Photos

B&B | 1 Bedroom | sleeps 5

1 night min stay

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from £62 /night

£428 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
Confort, tranquillità, storia ed enograstronomia  …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 - £990 / 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 £93 /night

£650 - £1590 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 3

2 Nights min stay

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from £54 /night

£377 - £556 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
La sua posizione strategica permette agli ospiti di assaporare appieno la tranquillità della vita di campagna e di raggiungere facilmente centri storici ed artistici dell'Italia centrale.  …see more

24 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 | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £358 /night

£2500 - £3291 / week

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Key info:

  • Nearest beach 135 km
  • 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 | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

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

23 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

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £217 /night

£1513 - £2380 / week

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Key info:

  • Nearest beach 135 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on a hillside and surrounded by the vineyards of a famous local wine producing farm, Villa Al Pozzo is the ideal place to spend a holiday in complete relaxation and tranquility. Independent villa of about 400 square meters that can accommodate up to 12 people.  …see more

23 Photos

Villa | 4 Bedrooms | sleeps 6

7 Nights min stay

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from £208 /night

£1452 - £1855 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Barbara is situated on the top of a hill kissed by the sun and caressed by the stars. Skilfully restored to keep its ancient charm untouched, it attracts with its solemn dignity and with marked environmental, landscaping.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £381 /night

£2662 - £4194 / 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

17 Photos

Farmhouse | 3 Bedrooms | sleeps 4

2 Nights min stay

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from £83 /night

£578 - £770 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Casa Luca country house with fireplace, two balcony, fully equipeed kitchen, TV SAT, Wi-Fi, CD Stereo, 2 bedrooms and 1 bathroom, perfect for a family with 2 or 3 children and also for 2 couples of adults. Casa Luca has two fantastic balcony with breathtaking views over the valley..  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £83 /night

£578 - £770 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Flat for 4 people with outdoor patio in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area. The flat is perfect for 4 adults or for a family with 2 children. The kitchen is fully equipped and both bedrooms have en-suite bathroom.  …see more

14 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £84 /night

£583 - £848 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Located in the heart of the Tuscan countryside, Borgo di Vagli is a quaint, meticulously restored 14th century Hamlet surrounded by a protected area of olive groves, fruit trees and ancient oaks.  …see more

12 Photos

Apartment | 6 Bedrooms | sleeps 20

1 night min stay

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from £26 /night

£180 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Casa faulle is een perfecte uitval basis voor het bezoeken van steden als Arezzo,Siena, Assisi ,Perugia ,Rome en Florence, alle binnen een 0,5 tot 1,5 uur. Het avontuur opzoeken samen met de beheerder is een uitdaging, samen een flinke wandelroute volgen. casa faulle is zeer geschikt als groepsaccommodatie met grote keuken met buiten en binnen eet gelegenheid.  …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

12 Photos

Hotel apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £184 /night

£1283 / 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
Appartamento in Leopoldina nel cuore della Valdichiana - Cortona AR con giardino privato, piscina privata campi da tennis e calcetto  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £80 /night

£556 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Casina via Iannelli offers you the opportunity to stay in the historic center of Cortona in a house of historical and artistic interest created and preserved until the beginning of 1300.  …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

21 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £98 /night

£686 - £1412 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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

20 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £142 /night

£992 - £1815 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Your very own piece of medieval Cortona! Gracious living in this superbly equipped, spacious "home from home" at the pedestianised heart of town. Enjoy a welcome retreat from the rigours of your day's sightseeing, before an evening of fine dining and quality shopping. Cortona continues to host immunerable weddings in its medieval town hall, with the famous photogenic steps!  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £86 /night

£599 - £1283 / 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

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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

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Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

4 Nights min stay

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from £318 /night

£2226 - £3922 / 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 Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more