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Cortona

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94 Holiday homes

Filters applied: Cot available (94)

(2) Excellent 

21

Holiday farmhouse with swimming pool in Cortona

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
“Stunning views, lovely house, helpful owner.” Cortona is a very picturesque medieval town and this villa is a longish walk from the town itself up a very windy road. The house is only a few years old but built in the style of the old houses. It has la  …see more

from £145 / night

£1009 - £1639 / week

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from £145 / night

18

Province of Arezzo / Cortona

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £505 / night

£3362 / week

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from £505 / night

(2) Excellent 

25

Mercatale di Cortona holiday home rental

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 22 km
  • Swimming pool
  • Child friendly
Charming stone farmhouse with original features. Perfect for family holidays. Private fenced pool, table tennis and Wifi Beautiful countryside views. Only 2 kilometres from a village with shops and restaurant. Sought after location on the Tuscany-Umbria border.  …see more

from £150 / night

£884 - £1550 / week

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from £150 / night

6

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

 …see more

Pricing unknown

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Pricing unknown

(2) Excellent 

11

Holiday villa in Cortona

Province of Arezzo / Cortona

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Dardano is a deceptively large house, full of atmosphere. It is a simple country home, basic even, but with an elemental charm. You drive up to the house with its ancient stone well and to one side there's a little vine-covered area for shady outdoor eating. The garde  …see more

from £165 / night

£1150 / week

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from £165 / night

(1) Excellent 

17

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Only 15 minutes from the villa you can easily access the Etruscan town of Cortona.  …see more

from £315 / night

£2200 - £3200 / week

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from £315 / night

(6) Very Good 

44

Holiday apartment rental

Cortona / Centoia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
Delightful spacious self catering apartment in beautifully restored 18th century Tuscan farmhouse with pool. Rural, quiet & relaxing yet close to the charming Etruscan town of Cortona & within easy reach of the major art & cultural centres of Tuscany & U  …see more

from £59 / night

£379 - £664 / week

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from £59 / night

(2) Excellent 

24

Holiday lodge in Cortona

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Fattoria Borgonuovo - L'OrtensiaCharming 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

from £55 / night

£379 - £547 / week

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from £55 / night

(9) Excellent 

32

Holiday home in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“Fabulous, breathtaking and relaxing - just the right place for a getaway.” The holiday was easy to arrange with good communication on location, directions etc. The villa was lovely and comfortable for our stay. You had the ability to dine inside or  …see more

from £245 / night

£1645 - £2028 / week

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from £245 / night

22

Holiday villa rental

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The Orangery” is a charming and cosy detached house wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely r  …see more

from £164 / night

£715 - £1257 / week

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from £164 / night

30

Province of Arezzo / Cortona

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £564 / night

£2311 - £3236 / week

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from £564 / night

(9) Excellent 

38

Holiday cottage with swimming pool in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“Tuscan Dream” I cannot say enough good things about this wonderful Tuscan Dream Villa. The owner Christine was on another continent went out of her way to make us feel at home and cater to our every need through email exchanges and her wonderful hou  …see more

from £245 / night

£1645 - £2023 / week

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from £245 / night

(8) Excellent 

55

Holiday apartment in Centoia

Cortona / Centoia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Great base for discovering Tuscany.” Peter and Nina's apartments are in an ideal situation for exploring Tuscany with the added bonus of a pool to relax by when you return from trips to the surrounding hilltop villages. Il Boccolio is spacious and  …see more

from £68 / night

£471 / week

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from £68 / night

(2) Excellent 

20

Holiday apartment in Cortona

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Piero's organic vegetable garden delights guests' palate with seasonal produce: fruit, tomatoes, courgettes, green beans, lettuce, aromatic herbs. On request a skilled mountain-bike guide can accompany guests to discover stunning paths and trails, but even on  …see more

from £59 / night

£337 / week

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from £59 / night

(1) Excellent 

12

Holiday apartment with swimming pool in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
Flat for 4 people with outdoor patio in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area. It is perfect for wheel-chairs users. The kitchen is fully equipped and there is a dishwasher and a fireplace.La Stalla has also a tipical  …see more

from £85 / night

£505 - £757 / week

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from £85 / night

(2) Excellent 

25

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fonte al Vento is a detached villa wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely respect the privacy of  …see more

from £420 / night

£2437 - £3984 / week

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from £420 / night

(2) Excellent 

22

Cottage rental in Cortona

Province of Arezzo / Cortona

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The most important aspects of Il Glicine are: Location, Size, Silence, Privacy, Cleanliness  …see more

from £68 / night

£471 / week

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from £68 / night

(2) Very Good 

59

Apartment accommodation in Centoia with shared pool

Cortona / Centoia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Ideal location for touring Tuscany and Umbria” La stufa is a comfortable and well furnished apartment with ample room for two couples to enjoy their stay. The front bedroom has a nice view of Cortona and the rear bedroom looks out over La Lombarda's l  …see more

from £93 / night

£610 - £1085 / week

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from £93 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £64 / night

£429 - £488 / week

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from £64 / night

(5) Excellent 

14

Holiday home in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“One of those experiences your memory plays over and over again, every time putting a smile on your face.” We spent the second week of a two week vacation in Tuscany at Borgo di Vagli. This was our 'down time' week, having done a lot of sightseeing fro  …see more

from £110 / night

£631 - £799 / week

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from £110 / night

(3) Very Good 

42

Holiday apartment with shared pool in Montalla

Cortona / Montalla

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
Started officially as a busines in 1994 but with previous experience of property rental in the precedent 10 years, Agriturismo Fontelunga is now a reference poit for those searching for a true Tuscan experience.W own same of the nicest accommodation in the traditio  …see more

from £135 / night

£718 - £1369 / week

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from £135 / night

(1) Excellent 

24

Holiday villa in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
“A true TUSCAN experience. Better than words can describe.” It is quite a challenge to put into words a description of this place, the family and the amazing time we had at Vila Papale. The house and the entire property has so much history and characte  …see more

from £125 / night

£870 - £2143 / week

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from £125 / night

20

Holiday villa rental

Province of Arezzo / Cortona

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
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

Pricing unknown

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Pricing unknown

26

Montalla holiday farmhouse rental

Cortona / Montalla

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
I our farm we have a number of houses left intact in theyr original stile.Viila la Bozza is ancient building near a small country village in the country in front of Cortona.Divided in 2 apartments of the same size, completely independent from each other you will  …see more

from £269 / night

£1425 - £2353 / week

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from £269 / night

(2) Very Good 

24

Lodge letting in Cortona with shared pool

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Fattoria Borgonuovo - Il GeranioCharming 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

from £67 / night

£463 - £547 / week

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from £67 / night

53

Cortona holiday villa rental

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
<p>Cortona Tuscan Villa with pool- rural views and two independent annexes within walking distance of the medieval walled town of Cortona.</p>  …see more

from £322 / night

£2250 - £3330 / week

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from £322 / night

(4) Very Good 

23

Holiday villa with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“The perfect base camp to travel around Tuscany” We stayed there for two weeks during the summer with our kids (6 and 2). The property is beautiful and very quiet, the view is amazing. The house was very old (about 400 years) but has just been renova  …see more

from £85 / night

£1093 / week

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from £85 / night

29

Cortona holiday villa rental

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Le Contesse is a beautiful independent villa lying on a hillside, a few minutes from the Etruscan town of Cortona. A large park with holm-oaks and secular trees surrounds the villa, which commands a stunning view over the Valdichiana. Le Contesse has been furnishe  …see more

from £541 / night

£3782 - £4202 / week

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from £541 / night

(9) Excellent 

33

Holiday villa in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“A slice of heaven” This is the most relaxing place I have ever been. I could look out at the view for days. Cortona is a wonderful town with some lovely eateries and cafes to watch the world go by. Make sure to take a stroll along the passegiata of  …see more

from £245 / night

£1645 - £2023 / week

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from £245 / night

11

Province of Arezzo / Cortona

2 9 Min stay varies

  • 2 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £110 / night

£475 - £648 / week

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from £110 / night

24

Cortona holiday lodge rental

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Fattoria Borgonuovo - La RosaCharming 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

from £55 / night

£379 - £547 / week

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from £55 / night

(2) Excellent 

27

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 135 km
  • Swimming pool
  • Child friendly
“Wonderful, true Italian experience"” Have stayed in many hotels and apartments all over the world and this was truly a 'stand-out.' From the moment our group of 8 arrived we were made to feel welcome by Manuela. Little, extra touches such as bruschett  …see more

from £380 / night

£2656 - £3429 / week

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from £380 / night

(12) Excellent 

42

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
“IDYLLIC VILLA IN AN IDYLLIC SETTING” Our stay commenced with prosecco and snacks served by the lovely pool after our late afternoon swim after arrival, which set the standard for the rest of our visit. The accommodation is of even better quality than  …see more

from £208 / night

£1454 - £3194 / week

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from £208 / night

(1) Excellent 

24

Apartment rental in Montalla with shared pool

Cortona / Montalla

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Equipped with chairs, shades, and beach beds.It has been restored with respect for the original stile and all the furniture are antique, you will have a warm and relaxing feeling when you enter Il Moro Novo.The house is located just outside a small country villa  …see more

from £59 / night

£309 - £583 / week

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from £59 / night

(7) Excellent 

30

Holiday villa in Farinaio

Cortona / Farinaio

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“great week” The owner is trying to do everything has a good time. We felt comfortable and had a lovely week. The house has three bedrooms on each side above, below are other beds in the living area at disposal. The land is terraced and therefore diffi  …see more

from £181 / night

£1261 - £2522 / week

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from £181 / night

(1) Excellent 

12

Holiday farmhouse rental

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
2 bedrooms, full kitchen, living room with sofa bed, bathroom with shower.  …see more

Pricing unknown

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Pricing unknown

(2) Very Good 

12

Holiday villa with shared pool in Cortona

Province of Arezzo / Cortona

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The sitting room has an old open fireplace and impressive, ancient wooden beams. Two comfy sofas are a nice modern addition! The dining room is authentic Italian 1950s decor under more seriously ancient ceiling beams. The atmosphere at San Silvestro is one of homely cou  …see more

from £93 / night

£650 / week

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from £93 / night

21

Holiday villa with swimming pool in Teverina

Cortona / Teverina

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Large house for up to 12 with private pool on tuscany-Umbria border. Complete peace and privacy, not over-looked. 5 minutes to a quiet village, 10 minutes drive to shops and restaurants. Pizza oven, wifi, satellite TV.  …see more

from £387 / night

£2708 / week

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from £387 / night

(3) Very Good 

11

Mercatale di Cortona holiday apartment rental

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children age 5+
Fantastic apartament with 3 bedrooms and 2 bathroom in a villa with swimming pool and baby playground area.Fantastic balcony to dine and relax outdoor with a breathtaking view. Living room with fireplace that gives a warm and relaxing atmosphere for a fall in Tuscany.La  …see more

from £106 / night

£631 - £925 / week

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from £106 / night

(8) Excellent 

30

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Wonderful house, with beautiful views and flexible set up.” The house can in fact be viewed as three separate apartments each with it's own amenities. This gives great flexibility for people to have some quiet time, whether you're travelling with frie  …see more

from £337 / night

£2522 - £3362 / week

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from £337 / night

Top Destination reviews

Charming Cottage Near Cortona, Garden, AC,WiFI
A Gem in Tuscany

The information provided by Cesare at the time of booking was the best we've ever had! On arrival, we were greeted with a very helpful introduction to "our home for the week". It was great having a welcome gift of wine, some delicious home grown plum … see more