Cortona Villas, Holiday rentals and apartments

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Cortona

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829 Holiday homes

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

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 £269 / night

£1878 - £2843 / week

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from £269 / night

7

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The apartment Olivo, located on the ground floor, has a separate entrance and it consists of: a kitchen, a bedroom, a bathroom with shower and independent heating.  …see more

from £36 / night

£483 / week

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from £36 / night

35

Holiday home in Cortona

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 9 km
  • Child friendly
  • Pet friendly
Casa indipendente, con uno stupefacente panorama. Potrete mangiare all'aperto gustando la bellezza della Valdichiana e di Cortona, sfondo su cui si staglia la figura del Palazzone, villa principesca del 1500 con la sua torre ed il suo muro merlato.In assoluta pri  …see more

from £81 / night

£571 - £746 / week

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from £81 / 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 £110 / night

£658 - £965 / week

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from £110 / night

(1) Very Good 

36

Holiday villa in Cortona

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Francesca is a beautiful villa located in the countryside in the green hills on the border between Tuscany and Umbria, a few kilometers from Cortona, a quaint town rich in history and offers shops and services of all kinds.  …see more

from £143 / night

£992 - £1685 / week

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from £143 / night

12

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden

 …see more

from £62 / night

£395 / week

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from £62 / night

19

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden
This generous and luxurious apartment is settled on the ground floor and each bedroom has it's own outside space. The different levels of a few steps gives it a charming feeling of a house without the weight of it. It is comfortable and tastefully furnished with al  …see more

from £176 / night

£1185 / week

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from £176 / night

18

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Dardano is a simple but charming 3 bedroom farmhouse sleeping up to 9 people. Outside guests enjoy a private garden and private swimming pool (open from mid May to the end of September each year). Inside it is furnished simply but tastefully in a traditional Tuscan styl  …see more

from £214 / night

£1495 - £1950 / week

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from £214 / night

100

Holiday villa in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
Set in Tuscany Italy, this charming villa is the perfect place for your holidays. The villa offers: a swimming Pool, an internet Connection .  …see more

from £166 / night

£1157 - £1951 / week

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from £166 / night

(4) Excellent 

24

Holiday apartment in Cortona

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Child friendly
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 an  …see more

from £72 / night

£439 - £558 / week

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from £72 / night

(3) Excellent 

34

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
This magnificent villa is located at 400 m from the lovely town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. This elegant vill  …see more

from £329 / night

£2299 - £3422 / week

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from £329 / night

55

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
It has a private patio, only shared with our other apartments, where you can have dine 'al fresco', or sunbathing with our sun chairs.  …see more

from £73 / night

£439 / week

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from £73 / night

(3) Excellent 

25

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £188 / night

£1316 - £1755 / week

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from £188 / night

14

Holiday apartment in Cortona

Province of Arezzo / Cortona

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
Apartments in historical center - Ville: La Piccionaia  …see more

from £351 / night

£2457 / week

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from £351 / night

23

Cortona / Fratta Santa Caterina

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £176 / night

£1316 / week

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from £176 / night

(1) Excellent 

19

Holiday villa rental

Cortona / Poggioni

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
L'agriturismo Poggio del Fabbro è situato in località San Pietro a Dame, frazione del comune di Cortona nella montagna cortonese, a 20km dalla città, in una posizione tranquilla e isolata tra le verdi montagne ad un'altezza di 700m slm al  …see more

from £113 / night

£786 / week

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from £113 / night

16

Province of Arezzo / Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £58 / night

£378 - £439 / week

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from £58 / night

(3) Excellent 

23

Holiday villa in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic cottage with beautiful view and surround” Good location and beautiful villages around the cottage. We also loved the view and the pool. The surround of the cottage was very tidy.  …see more

from £106 / night

£790 / week

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from £106 / night

(2) Excellent 

43

Holiday villa in Cortona

Province of Arezzo / Cortona

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Suitable for children age 5+
  • Private garden
Tuscany Cortona Ossaia Villa  …see more

from £53 / night

£351 - £720 / week

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from £53 / night

100

Apartment rental in Cortona with shared pool

Province of Arezzo / Cortona

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
These apartments offer luxury and comfort in a very tranquil and refined atmosphere. They share a fantastic garden and swimming pool, and they’re located in a very strategic location.  …see more

Pricing unknown

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Pricing unknown

(2) Very Good 

18

Holiday villa in Cortona

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
“Delivered the experience as promised” Both the accomodation and the rental experience were excellent - a lovely property, exactly as promoted, combined with superb, prompt and effective customer service. A great experience overall. Only proviso; the w  …see more

from £188 / night

£1316 - £2009 / week

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from £188 / night

34

Cortona / Montanare

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £62 / night

£395 - £527 / week

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from £62 / 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 £141 / night

£983 - £2174 / week

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from £141 / night

22

Holiday cottage with swimming pool in Cortona

Province of Arezzo / Cortona

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful holiday home near Cortona, is located at a 15 min drive (15km) from this famed Etruscan and medieval town, main cultural and artistic centre of the Val di Chiana after Arezzo. The cottage is the outbuilding of an old farmhouse,  …see more

from £116 / night

£808 - £1483 / week

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from £116 / night

37

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This magnificent villa is located at 400 m from the lovely town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. This elegant vill  …see more

from £376 / night

£2632 - £4088 / week

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from £376 / night

36

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Family friendly villa Luxury villas  …see more

from £339 / night

£2369 / week

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from £339 / night

100

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Reggia Etruria is a wonderful complex of 4 apartments in Tuscany, all fitted with modern amenities and extremely comfortable, surrounded by a splendid panoramic garden with swimming, pool, and located nearby Arezzo, Pienza, Siena, and Cortona.  …see more

Pricing unknown

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Pricing unknown

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).<br />The owners speak and understand fluent English.  …see more

from £58 / night

£395 - £571 / week

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from £58 / night

12

Holiday apartment rental

Cortona / Farinaio

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The apartment Uva, located on the first floor consists of: living room, kitchen, two bedrooms, a bathroom with shower and independent heating.  …see more

from £36 / night

£641 / week

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from £36 / night

24

Cortona / Mercatale di Cortona

5 11 4 nights min

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool

 …see more

from £198 / night

£1316 / week

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from £198 / night

26

Holiday farmhouse with golf nearby in Fratticciola

Cortona / Fratticciola

13 29 Min stay varies

  • 13 bedrooms
  • Sleeps 29
  • Min stay varies
  • Beach / lakeside relaxation
  • Air conditioning
  • 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<br />Breakfast ,Wine tasting , dinner with our local products on request.  …see more

from £483 / night

£3422 - £5834 / week

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from £483 / 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 £438 / night

£2544 - £4158 / week

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from £438 / night

8

Farinaio holiday apartment rental

Cortona / Farinaio

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees.Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating  …see more

from £36 / night

£702 / week

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from £36 / night

30

Holiday home in Cortona

Province of Arezzo / Cortona

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 15 km
  • Suitable for children age 5+
  • Air conditioning
5 min drive to Cortona. Perfect base to see the rest of Tuscany and Perugia. Personal chef for 1 day or more for cooking classes and/or privet dinners right next door.  …see more

from £66 / night

£351 / week

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from £66 / night

26

Villa rental in Cortona

Province of Arezzo / Cortona

6 15 2 nights min

  • 6 bedrooms
  • Sleeps 15
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
L'Agriturismo Villa Giarradea è una magnifica residenza signorile della fine del 600. Completamente ristrutturata mantenendo l'aspetto esterno originale (la villa è protetta dalle "belle arti"), la struttura è immersa nel verde d  …see more

from £115 / night

£799 / week

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from £115 / night

79

Cortona / Centoia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 16 km
  • Swimming pool

 …see more

from £105 / night

£696 - £1035 / week

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from £105 / night

27

Province of Arezzo / Cortona

3 7 7 nights min

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

 …see more

from £115 / night

£799 / week

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from £115 / night

(1) Average 

24

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £58 / night

£400 / week

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from £58 / night

100

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
This villa in Cortona’s countryside sleeps up to 4 people. It is fully equipped and it even boasts its own garden and swimming pool. It is close to the famous art cities in the region so it works as an ideal starting point for a holiday in Tuscany.  …see more

from £336 / night

£2348 / week

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from £336 / 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 £420 / night

£2939 - £4562 / week

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from £420 / night