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Villas in Cortona and Holiday rentals - Holiday Lettings - Holiday Rentals Cortona

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1,175 Holiday homes

Holiday villa with swimming pool in Cortona

Cortona villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

from £394 / night

£2,756 - £4,548 / week

1 / 24

Holiday villa in Cortona

Cortona villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £276 / night

£1,929 - £2,411 / week

1 / 72

Cortona holiday home rental

Cortona house

  • 13 bedrooms
  • 11 bathrooms
  • sleeps 24

from £1,068 / night

£6,523 - £9,110 / week

1 / 36

Holiday home with swimming pool in Mercatale

Mercatale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £145 / night

£1,013 / week

1 / 20

Home rental in Montalla with swimming pool

Montalla house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £195 / night

£1,364 - £3,289 / week

1 / 31

Holiday cottage with swimming pool in Montecchio, San Lorenzo

Montecchio, San Lorenzo cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 15

Cortona holiday home rental

Cortona house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £266 / night

£1,860 - £2,479 / week

1 / 44

Holiday home with swimming pool in Cortona

Cortona house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from £137 / night

£955 / week

1 / 31

Holiday villa with swimming pool in Cortona

Cortona villa

  • 10 bedrooms
  • 13 bathrooms
  • sleeps 20

from £2,888 / night

£20,215 / week

1 / 38

Teverina holiday home rental

Teverina house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from £160 / night

£1,114 - £1,963 / week

1 / 32

Holiday villa with swimming pool in Cignano

Cignano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 19

from £645 / night

£4,512 / week

1 / 54

Holiday villa rental

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 4

from £310 / night

£2,170 - £4,220 / week

1 / 48

Cortona holiday villa rental

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 6

from £273 / night

£1,910 - £3,582 / week

1 / 33

Holiday villa with swimming pool in Pietraia

Pietraia villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £774 / night

£5,415 / week

1 / 25

Cortona holiday villa rental

Cortona villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £255 / night

£1,785 / week

1 / 31

Holiday villa in Cortona

Cortona villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £434 / night

£2,411 / week

1 / 59

Holiday villa with swimming pool in Cortona

Cortona villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

from £276 / night

£1,929 - £3,443 / week

1 / 32

Cortona holiday home rental

Cortona house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £786 / night

£5,498 / week

1 / 24

Holiday villa rental

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

from £310 / night

£2,170 - £4,220 / week

1 / 41

Holiday villa with swimming pool in Cortona

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £433 / night

£3,032 / week

1 / 20

Holiday home with swimming pool in Cortona

Cortona house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £442 / night

£4,078 / week

1 / 63

Holiday villa in Cortona

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £583 / night

£4,699 / week

1 / 48

Holiday villa in Cortona

Cortona villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

from £1,252 / night

£8,760 / week

1 / 25

Holiday apartment in Cortona

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £146 / night

£1,019 / week

1 / 27

Holiday villa in Cortona

Cortona villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £873 / night

£6,107 / week

1 / 33

Villa rental in Cortona with swimming pool

Cortona villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £494 / night

£3,459 - £4,562 / week

1 / 40

Holiday farmhouse in Cortona

Cortona farmhouse

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

Pricing unknown

1 / 7

Holiday home in Cortona

Cortona house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 10

from £483 / night

£3,376 / week

1 / 29

Holiday villa with swimming pool in Cortona

Cortona villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £228 / night

£1,592 - £2,468 / week

1 / 132

Holiday villa with shared pool in Cortona

Cortona villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from £242 / night

£1,688 / week

1 / 18

Pietraia holiday villa rental

Pietraia villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

from £261 / night

£1,820 - £3,002 / week

1 / 49

Creti holiday villa rental

Creti villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £428 / night

£2,990 - £4,726 / week

1 / 60

Holiday villa with swimming pool in Teverina

Teverina villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

from £203 / night

£1,418 / week

1 / 38

Holiday cottage with shared pool in Cortona

Cortona cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £135 / night

£946 / week

1 / 24

Cortona holiday villa rental

Cortona villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £563 / night

£3,935 / week

1 / 3

Montalla holiday home rental

Montalla house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £201 / night

£1,407 - £2,565 / week

1 / 27

Holiday villa letting

Cortona villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

from £802 / night

£5,609 - £6,848 / week

1 / 73

Holiday villa rental

Montecchio villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 22

from £276 / night

£1,929 - £3,443 / week

1 / 55

Holiday villa with swimming pool in Cortona

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £482 / night

£5,833 / week

1 / 26

Cortona holiday villa rental

Cortona villa

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 22

from £820 / night

£5,739 / week

1 / 55

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Cortona holidays

With magnificent panoramas, great old Italian architecture and some of the best food in the area, Cortona is the ideal destination for a romantic getaway or family holiday. The cobblestone streets, quaint buildings, and winding roads of Cortona make it one of the best walking towns in the area. If you are looking for great restaurants and shopping, be sure to check out Piazza Signorelli.

Here are a few additional suggestions of things to do in Cortona:

  • Cooking Classes: Several hotels in the area offer half-day and full-day courses in the art of making traditional Italian dishes.
  • The Archaeological Park: This route takes you along several Roman roads and past some beautiful architecture.
  • Visit the Churches: Cortona is home to beautiful churches including the Duomo and Eremo Le Celle.
  • Visit the Tombs: The Etruscan tombs are arguably the biggest attraction in the area.
  • Palazzo Comunale: The town hall that was built in the early 13th century remains largely intact and offers guided tours.

Not surprisingly, many of the festivals in Cortona revolve around the amazing culinary attractions in the area. The biggest festival is the Sagra della Bisteca in August, which celebrates the steak from the local Chianina cows. The other main festival in the area is the Giostra dell'Archidado in May, an archery competition where representatives of the city's quarters compete while wearing historical costumes. The annual grape harvest, typically held in late September or early October, is another big event for Cortona.

Whether you want a condo with panoramic views of the vineyards out your front door, an apartment that's steps from all the major attractions and fine dining options, or a more secluded luxury villa in the outer parts of town, there's a holiday rental available to help you get the most out of your European getaway.

Top Destination reviews

Tenuta Angelici Winery Agriturismo Henni pool sauna jacuzzi panoramic view
Wonderful Villa with amazing views

A spacious comfortable villa equipped to a high standard that can easily accommodate 3 families with children. Garden/pool/pool house makes good use of the spacious garden with an outdoor dining/lounge area in the centre. Good service with the pool and hot tub cleaned on a regular basis throughout the week. Valentina helped to organise an evening with Christina who cooked wonderful authentic Toscany cuisine for both kids and grown ups, amazing! Wonderful views with Montepulciano in the horizon.see more
Holiday Villa in Cortona
Stunning villa, gracious owner

A group of 10 of us arrived for a week's stay in late July. The villa with 5 double en-suite bedrooms (all air conditioned) is immaculate. The lounge area and dining room are lovely but unused during our stay. The terrace is well situated and ideal for shade with transparent curtains for protection from occasional rain. Kitchen is small but adequate with plenty of crockery/cutlery for 10+ plus a dishwasher and coffee machine. There is a utility room with washing machine, tumble dryer plus games for outside The pool is lovely with enough sun beds for everyone and 6/8 parasols There is also a one bedroom annexe - again with aircon. This was ideal for a young couple in our party with a young baby. Therefore 6 doubles in total. On arrival a magnificent buffet was laid on the dining table which was really thoughtful - the following day was a Sunday and the villa is remote - many of our party were arriving late evening In all I would recommend the villa to anyone; you need a car as it is some distance from Cortona and the supermarket is downhill from there but the views are amazing and it's very peaceful. Grazia is a gracious host - she was so helpful - a very lovely lady. Please do not hesitate to book this villa - you won't be disappointedsee more
To Stones
A ‘gem’ in Cortona

Alle Pietre would without doubt, be the best holiday home we have stayed in over the past ten years. From the very beginning, the communication from Ester, the owner, was excellent and the welcome from both Ester and her husband Giovanni was wonderful - like meeting old friends, they were warm and genuinely wanted us to have a fabulous time - we did! The house is in the most perfect position by the wall looking into the valley below - watching the sunset from this spot was absolutely breath taking. The house has been recently renovated from top to bottom and to a very high standard, it is furnished with exquisite antique style furniture. The kitchen is exceptionally well equipped and bed linen and towels of a very high standard. Everything worked and Ester was just a txt message away if help was required. We absolutely loved our two weeks at Alle Pietre and are hoping to return next year. Thank you Ester and Giovanni for everything.see more
Six bedroom traditional Tuscan villa 5 minutes’ walking distance to Cortona!
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 bruschetta served to us on the night of arrival, to fresh flowers left on the outdoor table, made it a special time,in an amazing location. The sunsets, looking down over the valley, were simply stunning, as were the surrounding vistas. The villa itself was huge and beautifully decorated, with ample space for our large group. Can only dream of a return visit. Thanks Manuela for an unforgettable Italian experience.see more
villa ai cedri
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 really friendly and helpful any time you need something. They offer special Tuscan meals they prepare themselves. Some ingredients - like chicken, tomatoes, herbs - even come from the garden. A small wine cellar is at your disposal with a large selection of the owners wine - what a treat! The swimming pool is perfect; big and deep enough. You cannot only barbecue but bake your own pizza in the authentic stone oven. Cortona is a couple of kilometres away, a lovely place to visit. Other great sights like Arezzo, Assissi, Gubbio, etc. can be reached easily. All in all a great place to enjoy Italian friendliness and hospitality.see more
Stunning Tuscan villa with five bedrooms near Cortona, private pool and Wi-Fi!
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 character making this place a unforgettable experience. The gardens have a park like feeling, amazing trees, great pool and perfect views. We had barbecues and made bread and pizza in the wood oven in the back terrace almost every night during the stay. We were welcomed by the owners who also left a cake and a bottle of house wine for us in the kitchen. The INTUSCANY team that handled the booking was incredibly professional and we highly recommend them. All in all it comes to this > if you are looking for THE true tuscan experience, than this is surely the place to stay.see more

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