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

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2,865 Holiday homes

Holiday villa rental

Cortona villa

3 bedrooms • 4 bathrooms • sleeps 6

from £363 / night

£2,536 / week

1 / 27

Holiday home in Cortona

Cortona house

1 bedroom • 1 bathroom • sleeps 4

from £72 / night

£382 / week

1 / 30

Pietraia holiday villa rental

Pietraia villa

5 bedrooms • 7 bathrooms • sleeps 10

from £258 / night

£1,805 - £2,707 / week

1 / 49

Holiday apartment rental

Cortona apartment

2 bedrooms • 1 bathroom • sleeps 4

from £181 / night

£1,268 / week

1 / 24

Holiday home rental

Cortona house

1 bedroom • 1 bathroom • sleeps 2

from £48 / night

£286 / week

1 / 13

Cortona holiday home rental

Cortona house

13 bedrooms • 11 bathrooms • sleeps 26

from £726 / night

£4,433 - £9,862 / week

1 / 36

Holiday villa in Cortona

Cortona villa

2 bedrooms • 2 bathrooms • sleeps 4

from £274 / night

£1,913 - £2,391 / week

1 / 72

Cortona holiday apartment rental

Cortona apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £136 / night

£677 - £857 / week

1 / 29

Holiday home with swimming pool in Montecchio

Montecchio house

6 bedrooms • 5 bathrooms • sleeps 12

from £186 / night

£1,134 - £2,463 / week

1 / 36

Cortona holiday home rental

Cortona house

2 bedrooms • 1 bathroom • sleeps 5

from £106 / night

£641 - £1,104 / week

1 / 36

Cortona holiday home accommodation

Cortona house

2 bedrooms • 1 bathroom • sleeps 4

from £199 / night

£1,387 / week

1 / 15

Holiday home with swimming pool in Montalla

Montalla house

3 bedrooms • 3 bathrooms • sleeps 9

from £133 / night

£809 - £1,212 / week

1 / 36

Holiday home with swimming pool in Cortona

Cortona house

5 bedrooms • 5 bathrooms • sleeps 12

from £867 / night

£6,064 / week

1 / 19

Cortona holiday home rental

Cortona house

4 bedrooms • 4 bathrooms • sleeps 8

from £669 / night

£4,677 / week

1 / 13

Home accommodation in Cortona with shared pool

Cortona house

1 bedroom • 1 bathroom • sleeps 2

from £82 / night

£493 - £680 / week

1 / 32

Home rental in Cortona with shared pool

Cortona house

1 bedroom • 1 bathroom • sleeps 2

from £82 / night

£493 - £680 / week

1 / 32

Home rental in Cortona with shared pool

Cortona house

1 bedroom • 1 bathroom • sleeps 4

from £88 / night

£533 - £838 / week

1 / 32

Home rental in Cortona with shared pool

Cortona house

1 bedroom • 1 bathroom • sleeps 3

from £82 / night

£493 - £680 / week

1 / 32

Holiday home with shared pool in Montalla

Montalla house

1 bedroom • 1 bathroom • sleeps 4

from £64 / night

£385 - £572 / week

1 / 19

Holiday home in Montalla

Montalla house

1 bedroom • 1 bathroom • sleeps 3

from £59 / night

£355 - £513 / week

1 / 19

Cortona holiday home rental

Cortona house

2 bedrooms • 1 bathroom • sleeps 4

from £106 / night

£641 - £1,104 / week

1 / 36

Holiday home in Cortona

Cortona house

8 bedrooms • 7 bathrooms • sleeps 16

from £429 / night

£3,003 / week

1 / 29

Cortona holiday home rental

Cortona house

4 bedrooms • 5 bathrooms • sleeps 10

from £426 / night

£2,978 - £5,140 / week

1 / 24

Home rental in Cortona with shared pool

Cortona house

2 bedrooms • 2 bathrooms • sleeps 4

from £106 / night

£641 - £1,104 / week

1 / 36

Cortona holiday home rental

Cortona house

2 bedrooms • 2 bathrooms • sleeps 4

from £106 / night

£641 - £1,104 / week

1 / 36

Holiday apartment with shared pool in Cortona

Cortona apartment

1 bedroom • 1 bathroom • sleeps 2

from £143 / night

£811 / week

1 / 17

Holiday villa in Cortona

Cortona villa

5 bedrooms • 5 bathrooms • sleeps 10

from £420 / night

£2,936 - £3,423 / week

1 / 35

Holiday apartment with shared pool in Cortona

Cortona apartment

2 bedrooms • 1 bathroom • sleeps 4

from £191 / night

£858 / week

1 / 9

Holiday home with swimming pool in Cortona

Cortona house

4 bedrooms • 4 bathrooms • sleeps 8

from £385 / night

£2,689 - £3,056 / week

1 / 63

Cortona holiday villa rental

Cortona villa

6 bedrooms • 6 bathrooms • sleeps 12

from £582 / night

£4,068 - £6,175 / week

1 / 29

Holiday cottage with swimming pool in Montecchio, San Lorenzo

Montecchio, San Lorenzo cottage

1 bedroom • 1 bathroom • sleeps 2

Pricing unknown

1 / 15

Holiday apartment in Cortona

Cortona apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £67 / night

£382 / week

1 / 20

Holiday home with swimming pool in Cortona

Cortona house

4 bedrooms • 2 bathrooms • sleeps 9

from £136 / night

£947 - £1,904 / week

1 / 31

Holiday home with swimming pool in Mercatale

Mercatale house

3 bedrooms • 2 bathrooms • sleeps 8

from £96 / night

£668 / week

1 / 20

Cortona holiday home rental

Cortona house

5 bedrooms • 3 bathrooms • sleeps 10

from £264 / night

£1,844 - £2,323 / week

1 / 44

Teverina holiday home rental

Teverina house

4 bedrooms • 2 bathrooms • sleeps 7

from £143 / night

£1,001 - £1,764 / week

1 / 32

Cortona holiday villa rental

Cortona villa

10 bedrooms • 12 bathrooms • sleeps 22

from £715 / night

£4,289 - £6,196 / week

1 / 55

Cortona holiday home rental

Cortona house

3 bedrooms • 2 bathrooms • sleeps 6

from £191 / night

£1,335 / week

1 / 24

Cortona holiday apartment rental

Cortona apartment

2 bedrooms • 1 bathroom • sleeps 4

from £91 / night

£634 / week

1 / 22

Home rental in Cortona with shared pool

Cortona house

1 bedroom • 1 bathroom • sleeps 2

from £109 / night

£763 / week

1 / 13

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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

Casa del Balestriere In Centro Storico
Quiet spacious apartment

Wonderful base for a stay in Cortona. Two-floor one-bed apartment with lots of space, two bathrooms and a kitchen. Really well appointed with everything you need. It's a short stroll downhill into the centre of Cortona (steep walk back but only 5 mins). Just far enough away to be quiet despite festivities and celebrations in the centre. Host was so welcoming, collecting us from nearby carmucia train station and a delicious home made fruit tart. Would highly recommend.see more
Agriturismo Henni pool sauna jacuzzi panoramicview
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 house-the House Cells-
The Owner

Mauro, The owner was excellent to deal with. Even though we had to cancel, he went to lengths to be sure I was refunded my deposit. We look forward to staying at this charming Farm House next spring. Thank you Mauro! Chao!! ~Darlene M. … see 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
Holiday Villa in Cortona
Great vacation home!

Spent a week with the family in this house. We really enjoyed our stay. The house has great standard and is really spacious. Beautiful garden and pool area. The place is remote so a car is probably needed. Gracia and her family were incredibly helpful and kind in providing tips and responding to any questions we had. This place is much recommended!see more
Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views
Beautiful and relaxing stay

A lovely large house, which catered for all our needs in a peaceful location. The pool was cleaned each morning, shops are 10 mins away and the owners are very helpful. The views from Mandorli are stunning. We hope to return. … see more

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