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Cortona

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457 Holiday homes

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

(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 £185 / night

£1294 - £1725 / week

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from £185 / night

14

Home rental in Cortona

Province of Arezzo / Cortona

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
<p>Tucked away in the blissful rolling countryside on the edge of Cortona, this stone cottage with its private pool is a delightful hideaway for a couple<span class="x_style25">seeking to experience the best of Tuscany and Umbria.</span></  …see more

from £235 / night

£1640 - £2010 / week

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from £235 / night

23

Villa rental in Montanare

Cortona / Montanare

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Suitable for children age 5+
  • Ask about pets
  • Private garden
We restored this house 25 years ago. Is a lovely and peaceful house to stay in contact with the nature. You also have at close distance so many places to visit, the Trasimeno lake, Florence, Perugia, Pienza, Montefiascone, Città della Pieve, Gubbio, Assisi, Siena  …see more

from £156 / night

£819 - £1061 / week

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from £156 / night

14

Holiday apartment in Mercatale di Cortona

Cortona / Mercatale di Cortona

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
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

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26

Holiday villa rental

Cortona / Montecchio

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in a beautiful hilly position, Il Giardino di Diana is a genuine stone and brick farmhouse surrounded by the characteristic Tuscan hills with olive groves and vineyards. Both the pool and the attic, boast spectacular panoramic views of the countryside with Corto  …see more

from £247 / night

£1725 - £3018 / week

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from £247 / night

33

Cortona holiday villa rental

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
the innovative techniques for sustainable constructions intended to protect the environment.  …see more

from £271 / night

£1897 - £2544 / week

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from £271 / night

19

Province of Arezzo / Cortona

15 30 Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £733 / night

£4138 - £9182 / week

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from £733 / 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

(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 £145 / night

£1009 - £11281 / week

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from £145 / night

21

Holiday villa with swimming pool in Pietraia

Cortona / Pietraia

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 155 km
  • Swimming pool
  • Child friendly
In the verdant countryside in the heart of Tuscany close to Cortona, is located Villa Capezzine, which is a cosy retreat for your holidays in complete quiet and relaxation. The villa is bright and luminous furnished in keeping with the typical Tuscan style but with mod  …see more

from £111 / night

£776 - £1380 / week

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from £111 / night

30

Holiday home with swimming pool in Cortona

Province of Arezzo / Cortona

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Il Giardino di Silvana is a typical Tuscan stone house located on an evocative hilly position, a few steps away from the prestigious Santa Maria Nuova church and walk to town. The property preserves its rustic style with cotto flooring, wood beamed ceilings and Pietra  …see more

from £185 / night

£1294 - £2156 / week

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from £185 / night

33

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Surrounded by the gentle hills which frame the medieval town of Cortona, Villa Eugenio will assure you a peaceful vacation in the heart of Tuscany. This beautiful 17th century Tuscan farmhouse has been painstakingly restored and turned into a warm and welcoming country  …see more

from £191 / night

£1337 - £2130 / week

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from £191 / night

22

Holiday villa in Pietraia

Cortona / Pietraia

9 20 Min stay varies

  • 9 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
The farm houses Sant'Anna offers its guests a newly renovated hotel (2017), ideal for families and groups of friends. During the renovation special attention it was given to respect the architectural characteristics of the Tuscan houses, but will not sacrifice moder  …see more

from £409 / night

£2863 / week

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from £409 / night

25

Holiday villa in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £74 / night

£518 - £932 / week

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from £74 / 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

19

Apartment rental in Cortona

Province of Arezzo / Cortona

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
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 della campagna Corto  …see more

from £113 / night

£785 / week

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from £113 / night

19

Holiday villa in Cortona

Province of Arezzo / Cortona

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
Villa Bellora is an amazing property located in the Tuscan countryside between Cortona and Montepulciano, not far from Montepulciano lake. The Tuscan style of the typical farmhouse has been treasured by retaining the terracotta floors and wooden beams which characteriz  …see more

from £237 / night

£1656 - £2857 / week

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from £237 / night

100

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 136 km
  • Swimming pool
  • Child friendly
Villa Lucente is the perfect villa for those wanting an idyllic holiday in Tuscany. The villa is located in the heart of the Val di Chiana in Tuscany, near the enchanting town of Cortona, you'll enjoy breathtaking views of the surrounding countrysid  …see more

from £666 / night

£4656 - £5690 / week

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from £666 / night

(16) Excellent 

46

Home rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 10 3 nights min

  • 6 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“heaven on hearth” I stayed with a group of friends in this beautiful Tuscan farmhouse. We had such a great time. The house is full of charm and character and soo cool during hot summer afternoons, just heaven. The sourrounding areas are just stunni  …see more

from £156 / night

£949 - £1294 / week

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from £156 / night

100

Cortona holiday villa rental

Province of Arezzo / Cortona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly
Villa Corona is the best place for families and friends looking to spend their holidays relaxing in the stunning Val di Chiana.  …see more

from £265 / night

£1850 - £2759 / week

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from £265 / night

35

Holiday villa in Cortona

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Charming 175 sq.m villa for holidays in Tuscany, in the beautiful countryside surrounding the medieval city of Cortona, center of many important national and international cultural events. The villa is located in the Val d'Esse , between Tuscany and Umbria, in a v  …see more

from £185 / night

£1294 - £2069 / week

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from £185 / night

(5) Excellent 

4

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
“We have been visiting this delightful villa for the last 20 years.” We have been visiting this house for the last 20 years. We came here on honeymoon and have been returning, now with children, eversince. One of the best things about here is the delig  …see more

from £237 / night

£1655 / week

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from £237 / night

78

Holiday home with shared pool in Montecchio

Cortona / Montecchio

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stalla Cottage is an incredibly romantic, detached cottage with one bedroom + 1 bathroom. It opens onto a private garden with ecstatically beautiful views across the valleys that undulate into a depthless abyss of olive groves, orchards, honey fields of yellows, reds an  …see more

from £13 / night

£87 - £604 / week

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from £13 / night

100

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
This cozy villa in Cortona can accommodate up to 6 people. It has a swimming pool, a living room, 5 bedrooms and 5 bathrooms.  …see more

from £616 / night

£4311 / week

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from £616 / night

24

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden
This lovely apartment, located on the first floor and enhanced by a small equipped garden, is set in beautiful panoramic position at short distance from Cortona historic centre. Recently renovated, it can host up to 5 people in 3 bright bedrooms - 2 doubles and 1 single  …see more

from £87 / night

£345 - £690 / week

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from £87 / night

26

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
La Dolce Vita has been tastefully restored and decorated to the highest standards to produce a wonderful apartment in a quiet street a few minutes walk from the main square, bars and restaurants of Cortona. Picture windows in the living room and main bedroom provide stu  …see more

from £104 / night

£647 - £863 / week

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from £104 / night

24

Cortona holiday home rental

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Independent stone house at the foot of Cortona with swimming pool, garden  …see more

from £154 / night

£1078 / week

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from £154 / night

22

Holiday farmhouse rental

Cortona / Mercatale di Cortona

12 24 Min stay varies

  • 12 bedrooms
  • Sleeps 24
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool
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.<  …see more

from £453 / night

£3147 - £5556 / week

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from £453 / night

17

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
Dive in the pool of our rental house in Tuscany. A villa for your luxury vacation. Beautiful medieval stone hamlet situated in quiet and panoramic position between olive trees and woods of ancient chestnut trees, typical of Tuscany.  …see more

from £130 / night

£733 / week

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from £130 / night

95

Montecchio holiday home rental

Cortona / Montecchio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cerro + Castagna Cottage make up one extremely large apartment with a covered terrace/verandah - seats 6. Not only are there 2 double bedrooms + 2 bathrooms, there are also 2 sitting/dining rooms, each with a fully fitted kitchen, one of which is very large with a firep  …see more

from £111 / night

£776 - £949 / week

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from £111 / night

25

Cortona holiday apartment let

Province of Arezzo / Cortona

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Located right in the heart of the historic Tuscan hillside town of Cortona, The Painter's Nest is a great choice for those who want to stay in a characteristic ambiance with all of the modern conveniences. With a total of 220 sqm, three bedrooms and three bathroom  …see more

from £156 / night

£1087 / week

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from £156 / night

100

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
This lovely villa near Cortona can accommodate up to 10 people. It has a swimming pool and 3 bedrooms with en-suite bathrooms.  …see more

from £300 / night

£2095 - £3574 / week

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from £300 / night

25

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
At the foot of Cortona in a beautiful residential complex, antique oil mill, skilfully restored Sant'Angelo is a complete reconstructed Apartment respecting the characteristics of the epoch maintaining the original structure equipping it with every comfort of moder  …see more

from £95 / night

£432 - £733 / week

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from £95 / night

27

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Surrounded by the gentle rolling hills surrounding the ancient city of Cortona, Eugenio Villa offers an unforgettable holiday of privacy and tranquility. Careful restoration has transformed this typical Tuscan farmhouse of the XVII century in a house warm and cozy count  …see more

from £191 / night

£1337 - £2746 / week

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from £191 / night

24

Cortona holiday apartment rental

Province of Arezzo / Cortona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Apartment / Condo in Cortona with 4 bedrooms sleeps 8  …see more

from £263 / night

£1536 - £2005 / week

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from £263 / night

29

Holiday apartment in Cortona

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Set in the verdant hills of the Valdichiana on the border between the Provinces of Arezzo and Siena the Fattoria delle Chianacce is a typical farmhouse built in the last century. These farms produced some of the very best beef and pork in the area and many continue to d  …see more

from £43 / night

£294 - £544 / week

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from £43 / night

28

Holiday home with shared pool in Cortona

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cottage I Frati lies at the foot of the Cortona hill, just a few minutes drive from the famous Etrsucan town praised by Frances Mayes in her “Under the Tuscan Sun”. The estate is made up of a main house and Cottage I Frati. The owner, a famous pediatrician,  …see more

from £158 / night

£1104 - £1707 / week

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from £158 / night

35

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £185 / night

£1294 - £2069 / week

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from £185 / night

27

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
  • Ask about pets
it is the ideal place if you are looking to relax, private pool, and beautiful view.  …see more

from £88 / night

£613 - £888 / week

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from £88 / night

(3) Excellent 

43

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
Villa Rosa is a private home nestled in the hillside of the historic and vibrant hill top town of Cortona. A few minutes drive or a leisurely stroll into the City of Cortona, with expansive views over the valley to the distance shores of Lake Trasimeno Villa Rosa is  …see more

from £245 / night

£1645 - £2023 / week

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from £245 / night