Cortona apartment or villa with a private pool area | Holiday Lettings

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Cortona

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275 Holiday homes

Filters applied: Private pool

Travellers going to Cortona are booking June dates now. Secure your holiday home today and have the perfect trip.

(34) Excellent 

25

Holiday villa rental

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £200 / night

£1399 - £2500 / week

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from £200 / 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 £383 / night

£2678 - £3458 / week

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from £383 / night

24

Holiday villa rental

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
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. The perfect place for a holiday d  …see more

from £406 / night

£2839 - £4407 / week

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from £406 / night

(2) Excellent 

30

Province of Arezzo / Cortona

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 10 km
  • Swimming pool
  • Child friendly

 …see more

from £178 / night

£1246 / week

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from £178 / night

(1) Excellent 

27

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 £140 / night

£975 - £2162 / week

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from £140 / night

(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  …see more

from £113 / night

£790 - £1650 / week

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from £113 / night

(8) Very Good 

20

Holiday villa in Mercatale di Cortona

Cortona / Mercatale di Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 23 km
  • Swimming pool
  • Child friendly
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

from £122 / night

£849 - £1999 / week

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from £122 / night

(1) Excellent 

24

Holiday villa accommodation

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 161 km
  • Swimming pool
  • Child friendly
Villa Cortona is a beautifully restored luxury tuscan villa with 5 double bedrooms and 6 bathrooms.Each bedroom has its own different style and character and en-suite bathroom with wonderful views.The interior of Villa Cortona is large, bright and spacious,  …see more

from £412 / night

£2882 - £4577 / week

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from £412 / night

38

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 £309 / night

£2160 - £3200 / week

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from £309 / night

100

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
Villa Panorama is a 17th century farmhouse immersed in an oasis of peace and silence, yet near important and lively cultural centres such as Cortona, Arezzo, Siena and Perugia. The main villa can host up to 6 guests, while two annexes increase the c  …see more

from £260 / night

£1814 - £2746 / week

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from £260 / night

49

Holiday villa in Cegliolo

Cortona / Cegliolo

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa is located 2,5 km from Cortona. Recently renovated and nicely furnished, it is an 18th century Tuscan stone house. Surrounded by olive trees and facing south with lovely views across the valley below, Villa San Pietro is very private and quiet  …see more

from £291 / night

£2034 - £3475 / week

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from £291 / night

100

Holiday villa in Cortona

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
This villa with pool near Cortona in Tuscany can accommodate up to 8 people and features a kitchen, a dining room and two living rooms, 4 bedrooms and 4 bathrooms and breathtaking views over the Valdichiana.  …see more

from £295 / night

£2060 - £3513 / week

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from £295 / night

(2) Excellent 

20

Holiday cottage rental

Cortona / Mercatale di Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 20 km
  • Swimming pool
  • Child friendly
Baby-sitters or cooks on request for an additional cost. We run wine tastings to which you will be invited.  …see more

from £177 / night

£884 - £1508 / week

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from £177 / night

11

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Family friendly villa Budget Villas in Tuscany  …see more

from £287 / night

£2009 - £2903 / week

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from £287 / night

30

Province of Arezzo / Cortona

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £333 / night

£2331 - £3263 / week

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from £333 / 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

16

Bagnolo holiday villa rental

Cortona / Bagnolo

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This charming independent villa is situated in panoramic position in the Cortonese Mountains above the Etruscan hill town of Cortona. It's ideal location make it easy visit the most renowned historical and art cities of Tuscany and Umbria.  …see more

from £148 / night

£1030 - £1395 / week

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from £148 / night

(1) Excellent 

44

Cortona holiday villa rental

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.  …see more

from £136 / night

£950 - £1865 / week

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from £136 / 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

12

Holiday cottage with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Col di Leccio is a beautiful property made up of two stone cottages which enjoy a wonderful hilly position, a few minutes from the medieval town Cortona. Each house consists of two floors which host a cosy siting room with sofa and tv, dining area, fully fitted kitchen,  …see more

from £183 / night

£1272 - £2119 / week

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from £183 / night

(1) Excellent 

4

Holiday farmhouse with swimming pool in Mercatale

Cortona / Mercatale

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Private garden
Umbria Mercatale Tuscany Farmhouse  …see more

from £678 / night

£3390 / week

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from £678 / night

(1) Excellent 

27

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £84 / night

£551 / week

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from £84 / 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 £423 / night

£2458 - £4017 / week

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from £423 / night

(12) Excellent 

35

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“A marvellous house with a beautiful panorama view” A beautiful house in a peaceful area with a wonderful view to the valley. There are lovely rooms with tasteful furniture. Although the owners live next door, they do not disturb at all, they are real  …see more

from £218 / night

£1526 - £2458 / week

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from £218 / night

(3) Excellent 

21

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 26 km
  • Swimming pool
  • Child friendly
“Amazing view and the place to recover from the hustle n bustle of life” House that has been lovingly restored by the owners. Great outdoor space for entertainment and just to chill out with one's family. The caretaker family was very helpful. The main  …see more

from £454 / night

£3173 / week

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from £454 / night

37

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 25 km
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £365 / night

£2543 - £3331 / week

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from £365 / night

(4) Excellent 

4

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
“An enchanting holiday” My husband and I and our 4 children, aged 4 to 14, spent a week in June at Casa Francesca.The gardens were a sea of yellow Spanish broom and pink dog-rose with lavender and rosemary preparing to bloom around the pool and the hou  …see more

from £212 / night

£1484 / week

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from £212 / night

35

Cortona / Bagnolo

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £183 / night

£1276 / week

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from £183 / night

20

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 15 7 nights min

  • 5 bedrooms
  • Sleeps 15
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
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

from £424 / night

£2967 / week

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from £424 / night

18

Holiday villa rental

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Villa San Martino is set in a delightful position among extensive grounds overlooking the countryside. The swimming pool is surrounded by olive trees and lush gardens. The nearest town is Cortona, famous for its ancient backgrounds, home town of famous painter Luca Sig  …see more

from £144 / night

£1007 - £1992 / week

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from £144 / 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
“Wonderful Stay” This place turned out to be perfect for me and my wife. It was well located just outside Cortona but a short walking distance to a local cafe and restaurant. It is very private and on a beautiful property with gorgeous views. It has a  …see more

from £245 / night

£1645 - £2023 / week

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from £245 / 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.&l  …see more

from £106 / night

£636 - £933 / week

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from £106 / 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

(5) Excellent 

24

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Cortonese hillside, La Fortezza and the ancient wall which encloses the town, dominate the view of the surrounding hillside. Guests have exclusive use of the delightful 12x6 swimming pool, with Roman steps, which lies in an extremely panoramic position and from whe  …see more

from £142 / night

£992 - £11089 / week

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from £142 / night

16

Cortona holiday villa accommodation

Province of Arezzo / Cortona

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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

from £97 / night

£678 - £1017 / week

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from £97 / night

28

Cortona holiday villa rental

Province of Arezzo / Cortona

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Nestled in lush park surroundings, Villa Panphilii is a stunning 18th century villa located in Cortona, an ancient Etruscan city. The villa is set in breath-taking natural scenery, changing in colour and shades throughout the year, creating a unique atmosphere. There is  …see more

from £485 / night

£3390 - £4831 / week

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from £485 / night

29

Cottage rental in Pietraia with swimming pool

Cortona / Pietraia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, Il Nido is a lovely small villa recently restored and finely appointed with a contemporary country-chic style. The skillful ability in matching the soft tones and the tasteful reca  …see more

from £103 / night

£721 - £1695 / week

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from £103 / night

23

Holiday villa with swimming pool in Poggioni

Cortona / Poggioni

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Il Biancospino is a gracious property ideal for families and small groups, immersed in the greens of the cortonese mountains between oak and chestnut trees.  …see more

from £137 / night

£958 - £2119 / week

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from £137 / night

(1)  

33

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villas in Cortona - Ville: La Certosa  …see more

from £485 / night

£3390 - £4280 / week

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from £485 / night

(1) Very Good 

31

Holiday villa accommodation

Cortona / Mercatale di Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Located 800 meteres above sea level, overlooking the Val di Pierle, which is the most eastern area of the town of Cortona, in the tranquillity of the verdant Hills of Tuscany, IL CASALE DI CARMINA is an old mansion completely restored and furnished in a rustic style wit  …see more

from £128 / night

£1187 / week

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from £128 / night