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189 Holiday homes in Cortona

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189 Results  |  
21 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4/5 

2 Nights min stay

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from £97 /night

£675 - £1089 / 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

10 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £173 /night

£1210 - £2420 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa il Pino is an old farmhouse carefully restored while maintaining the aesthetic standards of the old Tuscan farmhouses using the original materials, such as roofing tiles, the handmade terracotta tiles for the floors, doors and windows all handcrafted in solid che  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

7 Nights min stay

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from £173 /night

£1210 - £2420 / 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

24 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £102 /night

£711 - £1474 / 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

23 Photos

Villa | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £47 /night

£323 - £686 / 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

23 Photos

Villa | 2 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

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from £70 /night

£484 - £807 / 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

21 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £223 /night

£1560 - £1880 / 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

14 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £223 /night

£1560 - £1880 / 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

19 Photos

Villa | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £223 /night

£1560 - £1880 / 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

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
  • 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

11 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

2 Nights min stay

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from £87 /night

£605 - £888 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
  • Private garden
Fantastic apartament with 3 bedrooms and 2 bathroom in a villa with swimming pool and baby playground area. La Loggia has also a tipical tuscany stone fireplace fantastic to there during the winter.  …see more

30 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

Short stays welcome

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from £104 /night

£726 - £971 / 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

14 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £79 /night

£550 - £800 / 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

21 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £81 /night

£565 - £1210 / 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

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

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

24 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

2 Nights min stay

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from £45 /night

£315 - £484 / 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

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

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from £127 /night

£888 - £1210 / 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

Apartment | 2 Bedrooms | sleeps 7

Excellent 5/5 

5 Nights min stay

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from £104 /night

£726 / week

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Key info:

  • Nearest beach 129 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
Breathtaking view from a unique Apartment between Cortona and Montepulciano. Luxury furnished, very well situated and ideal to relax and also to start daily drives into the best places of Tuscany and Umbria.  …see more

24 Photos

Townhouse | 1 Bedroom | sleeps 2

Excellent 5/5 

1 night min stay

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from £43 /night

£299 - £388 / 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

10 Photos

Farmhouse | 1 Bedroom | sleeps 4

Very Good 4/5 

2 Nights min stay

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from £49 /night

£339 - £380 / 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
The apartments is independent, and has beautiful piece of ancient furniture own heating system, some of them have a fire-place.  …see more

21 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £223 /night

£1560 - £1880 / 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 | 9 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £52 /night

£363 - £726 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
around the Villa La Fontana: The Parco del Trasimeno runs along the perimeter of Trasimeno lake and is the largest regional park in Umbria. The park includes three islands: the largest is Polvese Island, which is under the control of the Province of Perugia. Stunning Luxury villa in walking distance from Cortona  …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

13 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £47 /night

£323 - £525 / 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

10 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

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from £35 /night

£242 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
L'Etrusca e' un alloggio perfetto per chi vuole trascorrere le sue vacanze nel cuore della citta' e vivere direttamente la nostra tradizione Near of the most important Tuscany and umbria Town like: Firenze, Arezzo, Montepulciano, Pienza, Montalcino,  …see more

23 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £64 /night

£444 - £968 / 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 essential, internet wifi  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £51 /night

£355 - £525 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
L'edificio è circondato da un parco attrezzato con panchine, sdraio, dondolo, amaca ed illuminazione esterna. Tra abeti, cipressi ed altri alberi d'alto fusto nidificano varie specie d'uccelli che col loro cinguettio animano la quiete circostante.  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

2 Nights min stay

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from £33 /night

£230 - £355 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
La villa di campagna “I Nidi di Cortona” è situata in campagna, presso il piccolo borgo rurale di San Marco in Villa (sec. XIV), ai piedi della collina su cui si distende la cittadina etrusca di Cortona.  …see more

12 Photos

House | 6 Bedrooms | sleeps 6

Very Good 4/5 

Min stay varies

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from £116 /night

£807 / 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
-  …see more

6 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

Min stay varies

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from £116 /night

£807 / 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
-  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £335 /night

£2339 - £3428 / 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

21 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £85 /night

£593 - £783 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Charming small villa near Cortona, large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. The perfect base to explore Tuscany and Umbria. Very comfortable, fully equipped. Stunning countryside. Free GPS, Italian cell phone,laptop. Swimming pools/thermal spas. Great restaurants. Short walk to village.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £248 /night

£1732 - £2142 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Villa in Cortona with 3 bedrooms sleeps 6  …see more

11 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

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from £328 /night

£2295 - £4195 / 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

27 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

22 Photos

Farmhouse | 12 Bedrooms | sleeps 22

2 Nights min stay

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from £369 /night

£2581 - £4113 / 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
Villa Cuiano is a sprawling farmhouse with marvelous panoramic views of the Niccone Valley and the mountains of Umbria. The farmhouse has been divided in self-cointained apartments, that possible to rent separated too. Four fireplaces in flats and pizza oven outdoor. Villa with Pool, Terrace, Cook service, Playground, BBQ: sleeps 2 to 24 in 6 flat renting separated too.  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £149 /night

£1041 - £1734 / 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

22 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £88 /night

£614 - £1009 / 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

17 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

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from £315 /night

£2200 - £3200 / 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

23 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £150 /night

£1049 - £2017 / 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

11 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £93 /night

£646 - £1291 / 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

21 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £100 /night

£696 - £1129 / 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
Private independent accommodation with private garden area, private parking and independent entrance. The shared swimming pool area is very large and used from no more than 3 family at the time.  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £75 /night

£525 / week

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Key info:

  • Ask owner if 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

22 Photos

Villa | 4 Bedrooms | sleeps 6

6 Nights min stay

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from £77 /night

£533 - £888 / 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

15 Photos

Cottage | 1 Bedroom | sleeps 2

4 Nights min stay

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from £58 /night

£404 - £505 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car advised
  • No pets allowed
Character detached chestnut beamed cottage just below Cortona with terracotta tiles to sleep two with shared pool.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £125 /night

£871 - £1573 / 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

14 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

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from £162 /night

£1130 - £1412 / 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

6 Photos

Guest house | 6 Bedrooms | sleeps 25

1 night min stay

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from £74 /night

£517 - £807 / 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

18 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £277 /night

£1936 - £2517 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Bella is a stunning, luxury villa nestled in the Valdichiana valley just a few kilometres from Cortona. An ideal destination for exploring the beautiful regions of Tuscany and Umbria.  …see more

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