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.

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 £251 / night

£1755 - £3071 / week

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from £251 / night

16

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 6  …see more

from £68 / night

£395 - £692 / week

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from £68 / night

15

Montalla holiday home let

Cortona / Montalla

4 8 7 nights min

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

from £239 / night

£1667 / week

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from £239 / 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

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 £241 / night

£1685 - £2908 / week

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from £241 / 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 £416 / night

£2913 / week

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from £416 / night

11

Province of Arezzo / Cortona

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min

 …see more

from £65 / night

£452 / week

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from £65 / night

24

Holiday home in Cortona

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Private garden
Walking distance to the town Luxury villas Villas in Tuscany for groups  …see more

from £396 / night

£2772 - £3579 / week

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from £396 / night

17

Province of Arezzo / Cortona

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £106 / night

£658 - £790 / week

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from £106 / night

25

Holiday home with swimming pool in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Nestled deep within the hills of Tuscany yet only 500 metres from all the attractions of Cortona, this comfortable house is an ideal retreat for 4 nature-loving or wine-loving holidaymakers. Inside the house, the lounge is perfect for unwinding after a day of explorat  …see more

from £84 / night

£454 - £793 / week

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from £84 / 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 £461 / night

£3202 - £5653 / week

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from £461 / night

42

Villa accommodation in Cortona with swimming pool

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa di Costantino is a typical Tuscan stone built manor, surrounded by a large garden and located in a beautiful spot at the bottom of the hill of the Etruscan old town of Cortona that offers outstanding views over the Valdichiana. The house is spacious and welcoming,  …see more

from £195 / night

£1360 - £2457 / week

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from £195 / night

44

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £358 / night

£2500 - £3759 / week

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from £358 / night

(11) Very Good 

28

Province of Arezzo / Cortona

11 24 Min stay varies

  • 11 bedrooms
  • Sleeps 24
  • Min stay varies
  • Nearest beach 8 km
  • Swimming pool
  • Child friendly

 …see more

from £44 / night

£308 - £5299 / week

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from £44 / night

24

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in Cortona with 6 bedrooms sleeps 12  …see more

from £396 / night

£2772 - £3579 / week

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from £396 / night

27

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
The main apartment is spread over three floors linked by a modern crystal and steel staircase. On the first floor, the open space living area consists of a large well-equipped kitchen (with oven, fridge and dishwasher) and a bright large dining/living room with old ston  …see more

from £132 / night

£922 - £1097 / week

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from £132 / night

52

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 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 £274 / night

£1917 - £3171 / week

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from £274 / night

4

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £69 / night

£479 / week

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from £69 / night

10

Apartment rental in Cortona

Province of Arezzo / Cortona

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
Located in the heart of the medieval city centre of Cortona, this recently restored apartment offers all modern comforts. Sitting on two floors and with a total of two bathrooms and three bedrooms, there is definitely plenty of room. The modern concept of this apartme  …see more

from £351 / night

£2457 / week

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from £351 / night

(4) Excellent 

13

Province of Arezzo / Cortona

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 15 km
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

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 £113 / night

£790 - £1404 / week

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from £113 / night

16

Holiday home with swimming pool in Cortona

Province of Arezzo / Cortona

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Family friendly villa Villas in Tuscany for groups  …see more

from £308 / night

£2150 - £3071 / week

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from £308 / 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 £106 / night

£658 - £878 / week

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from £106 / night

30

Province of Arezzo / Cortona

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

 …see more

from £69 / night

£479 / week

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from £69 / night

100

Holiday apartment in Cignano

Cortona / Cignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
This agriturismo features a large outdoor pool and has seven apartments that can accommodate between 2 and 8 people.  …see more

from £110 / night

£676 - £1167 / week

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from £110 / night

100

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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

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 £158 / night

£834 - £1079 / week

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from £158 / night

(1) Excellent 

71

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £62 / night

£430 / week

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from £62 / 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 £305 / night

£2132 - £3636 / week

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from £305 / 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 £76 / night

£527 - £948 / week

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from £76 / night

100

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
This villa mixes the unique Tuscan style with elegant and modern comforts, and it is the perfect getaway for a family. It affords its own kitchen, 2 bedrooms and 2 bathrooms and a garden with swimming pool, BBQ area and spectacular views.  …see more

from £180 / night

£1255 / week

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from £180 / 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 £188 / night

£1316 - £2106 / week

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from £188 / night

8

Holiday apartment with swimming pool in Cortona

Province of Arezzo / Cortona

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Le Gelosie apartments” are the natural and inviting alternative to our hospitality and combine good taste and attention for details.  …see more

from £88 / night

£615 / week

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from £88 / night

16

Holiday apartment with shared pool in Fratticciola

Cortona / Fratticciola

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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

from £151 / night

£1053 / week

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from £151 / night

23

Province of Arezzo / Cortona

2 5 Min stay varies

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

 …see more

from £62 / night

£395 - £527 / week

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from £62 / 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 £195 / night

£1360 - £2167 / week

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from £195 / 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 £97 / night

£439 - £746 / week

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from £97 / night

(1) Excellent 

81

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 18 km
  • Swimming pool

 …see more

from £88 / night

£527 - £860 / week

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from £88 / 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

£299 - £553 / week

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from £43 / night

44

Holiday home in Cortona

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Air conditioning
Cortona is famous as the inspiration and setting for the book Under the Tuscan Sun, (that later became a movie) written by USA writer-novelist Francis Mayes. It also homes a branch of the Georgia University - USA, for artistic matters, since 1970.  …see more

from £128 / night

£759 - £851 / week

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from £128 / night