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332 Holiday homes in Cortona

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332 Results  |  
7 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £258 /night

£1802 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A family home with outstanding views of Cortona, set on the Tuscan/Umbrian border.  …see more

21 Photos

Farmhouse | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £142 /night

£992 - £1488 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Charming country house with private pool to rent at 1 mile from Cortona – sleeps 6+1 From 1200€ to 1800€ a week  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 5

Very Good 4/5 

7 Nights min stay

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from £85 /night

£590 - £990 / week

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Key info:

  • Swimming pool
  • Suitable 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

Featured properties

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
  • Suitable 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

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £306 /night

£2136 - £3286 / week

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Key info:

  • Suitable 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

19 Photos

Lodge | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £57 /night

£395 - £605 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Fattoria Borgonuovo - L'Ortensia Charming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m). The owners speak and understand fluent English.  …see more

19 Photos

Lodge | 1 Bedroom | sleeps 4

3 Nights min stay

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from £57 /night

£395 - £605 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Fattoria Borgonuovo - La Rosa Charming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m). The owners speak and understand fluent English.  …see more

14 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £84 /night

£583 - £742 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable 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

23 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £224 /night

£1562 - £1893 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £136 /night

£948 - £2019 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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 £366 /night

£2562 - £3290 / week

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Key info:

  • Swimming pool
  • Suitable 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £189 /night

£1323 - £2067 / week

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Key info:

  • Swimming pool
  • Suitable 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

11 Photos

Apartment | 4 Bedrooms | sleeps 5

2 Nights min stay

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from £51 /night

£351 - £570 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable 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

10 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £38 /night

£263 - £351 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £343 /night

£2397 - £3802 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable 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

22 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £63 /night

£437 - £623 / week

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Key info:

  • Nearest beach 165 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
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 | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £130 /night

£910 - £1488 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Il Fattore is a two bedrooms apartment sleeping 4+3 and it is part of an elegant and charming complex which has both hotel rooms and apartments to suit all types of holiday makers. It is a place full of magic for a stylish and elegant stay.  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £51 /night

£351 - £526 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £414 /night

£2893 - £5786 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Suitable 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

19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £107 /night

£748 - £1371 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
The beautifully decorated Tuscan-villino is surrounded by cypresses, old pines and olive trees, the residences offer magnificent views of the enchanting Valdichiana, a rolling countryside of sunflowers and vineyards. Excellent Restaurant by the pool .  …see more

21 Photos

Chalet | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £124 /night

£868 - £1126 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
All the independent property available. A nice shady garden of 2000 square meters, a gazebo, relaxing and a great barbecue for outdoor grilling watching the sunset. Ms. Paola will take care of the guests!  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 16

Min stay varies

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from £586 /night

£4100 - £6943 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Restored to high standard. Accommodation split in two private buildings. Ideal location between South Tuscany and Umbria. Private tennis court.  …see more

17 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

Min stay varies

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from £163 /night

£1139 - £1490 / week

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Key info:

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

11 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £179 /night

£1253 - £1446 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Ground floor 157 sqm suite with private terrace view to Cortona hill town, excellent point for day tours, near many cities in Tuscany and Umbria, such as Montepulciano, Arezzo, Assisi,Siena, Florence. great events during summer time, and many activities for the family. Stay in Tuscany with Activities at the Apartment Hotel La Mucchia  …see more

20 Photos

Hotel apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £76 /night

£526 - £745 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
We are located in the best point for day trips, you can visit many cities around within an hour drive, our apartment hotel is an medieval farm build 300 years ago and turned to luxurious apartments with all the comforts, still kept its original old world style.  …see more

17 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £138 /night

£964 - £1157 / week

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Key info:

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

20 Photos

Villa | 13 Bedrooms | sleeps 30

Excellent 5/5 

3 Nights min stay

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from £76 /night

£526 - £9891 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
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

21 Photos

Farmhouse | 1 Bedroom | sleeps 3

Min stay varies

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from £90 /night

£627 - £820 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
La Mucchia Casa Vacanza & Art Gallery is located in the Tuscany region in the best location for day trips and short excursions for short drives. The villa in Cortona is situated at the foot of the hills around the Cortonese Valey, called Valdichiana. “La Mucchia casa vacanza & art gallery”, being one of the most luxurious vacation villas in Tuscany  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £79 /night

£552 - £964 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £63 /night

£439 - £684 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Apartment for a couple or a family with one or two children in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area. The kitchen is fully equipped and big and lighting bedroom have en-suite bathroom.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £38 /night

£263 - £701 / week

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Key info:

  • Swimming pool
  • Suitable 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

12 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £79 /night

£552 - £964 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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 there is dishwasher and fireplace. La Stalla has also a tipical tuscany stone fireplace fantastic to there during the winter.  …see more

17 Photos

Farmhouse | 3 Bedrooms | sleeps 4

2 Nights min stay

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from £79 /night

£552 - £964 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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 or 4 children. Casa Luca has also a mansard bedroom suitable for other 2 children.  …see more

17 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £63 /night

£439 - £684 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Apartment for a couple or a family with one or two children in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area. The kitchen is fully equipped and bedroom have en-suite bathroom. Large area to dine outdoor, wi-fi free available.  …see more

22 Photos

Farmhouse | 12 Bedrooms | sleeps 24

2 Nights min stay

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from £351 /night

£2453 - £4994 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

20 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £100 /night

£699 - £1999 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Suitable 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

14 Photos

Farmhouse | 10 Bedrooms | sleeps 10

2 Nights min stay

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from £48 /night

£333 - £1577 / week

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Late Deal: save up to €896 (approx. £740)

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Prestigious country house immersed in the green countryside offers joyful days of rest  …see more

11 Photos

Farmhouse | 13 Bedrooms | sleeps 26

3 Nights min stay

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from £98 /night

£684 - £833 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
I manage this villa 's family and I will be very happy to help you during your stay! Welcome in a lovely place where you hearing birds! Ciao Breakfast on request Wine tasting , Tours on request Special Tuscany dinner on request  …see more

11 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £273 /night

£1908 - £4982 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • 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

20 Photos

Villa | 7 Bedrooms | sleeps 15

Short stays welcome

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from £272 /night

£1900 - £2900 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

15 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £101 /night

£703 - £1612 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Independent stone house close to Cortona, a former middle age tower with terracotta floors and gothic windows. 8 sleeps, swimming pool  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £89 /night

£620 - £1034 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Independent stone house at the foot of Cortona with swimming pool, garden  …see more

21 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £107 /night

£744 - £1405 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 15

7 Nights min stay

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from £284 /night

£1984 - £2893 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £201 /night

£1405 - £2852 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Suitable 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

9 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £57 /night

£397 - £910 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
The il Borgo Agritourism Complex is near the historic Etruscan city of Cortona. It is in a beautiful country setting amongst olive trees, cypresses and sunflowers in the Chiana Valley.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £94 /night

£653 - £976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
In the surroundings of Cortona, one of the most wonderful cities of art in Tuscany, lies the Agriturismo Isolina, deep in the green hills of the valley Valdichiana.  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £95 /night

£662 - £1240 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Casa Patrizia is a typical holiday house. The villa has a completely independent apartment on the ground floor with two entrances, with private garden, veranda with table and chairs, elegantly furnished and decorated in typical Tuscan style.  …see more

16 Photos

Cottage | 2 Bedrooms | sleeps 5

Short stays welcome

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from £48 /night

£331 - £496 / week

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Key info:

  • Nearest beach 10 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Cortona,Panoramic view, close to town, garden, barbecue.  …see more

8 Photos

House | 2 Bedrooms | sleeps 5

Min stay varies

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from £60 /night

£414 - £579 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
3-room semi-detached house 100 m2 on 1st floor, spacious, comfortable furnishings: living room with 1 sofa bed, open fireplace and satellite-TV. Exit to the loggia.  …see more