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

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3,648 Holiday homes

Holiday apartment with shared pool in Fratta Santa Caterina

Fratta Santa Caterina apartment

1 bedroom • 1 bathroom • sleeps 4

3 Reviews

from £63 / night

£436 - £790 / week

Holiday apartment with shared pool in Fratta Santa Caterina

Fratta Santa Caterina apartment

2 bedrooms • 1 bathroom • sleeps 3

1 Reviews

from £57 / night

£390 - £699 / week

Holiday villa with swimming pool in Cortona

Cortona villa

4 bedrooms • 5 bathrooms • sleeps 8

from £395 / night

£1,479 - £3,106 / week

Holiday farmhouse with swimming pool in Creti

Creti farmhouse

6 bedrooms • 5 bathrooms • sleeps 14

from £353 / night

£2,465 - £3,747 / week

Cortona holiday cottage rental

Cortona cottage

3 bedrooms • 3 bathrooms • sleeps 8

7 Reviews

from £149 / night

£1,042 / week

Holiday apartment with shared pool in Fratta Santa Caterina

Fratta Santa Caterina apartment

1 bedroom • 1 bathroom • sleeps 2

1 Reviews

from £60 / night

£413 - £733 / week

Holiday villa rental

Montecchio villa

6 bedrooms • 4 bathrooms • sleeps 12

10 Reviews

from £282 / night

£1,972 - £3,451 / week

Cortona holiday villa rental

Cortona villa

4 bedrooms • 5 bathrooms • sleeps 8

from £395 / night

£1,479 - £3,106 / week

Holiday cottage with shared pool in Cortona

Cortona cottage

2 bedrooms • 1 bathroom • sleeps 4

4 Reviews

from £145 / night

£1,016 / week

Cottage rental in Pietraia with swimming pool

Pietraia cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £120 / night

£838 - £1,972 / week

Holiday villa with swimming pool in Cortona

Cortona villa

5 bedrooms • 5 bathrooms • sleeps 11

1 Reviews

from £345 / night

£1,479 - £3,106 / week

Holiday cottage with swimming pool in Cortona

Cortona cottage

2 bedrooms • 2 bathrooms • sleeps 5

“Little spot of Italian Heaven” My favorite time of day at Villa Rosa is early morning when the sun burns away the mist in the valley, and all you can hear are birds, thousands and thousands of birds! There are even a few cuckoo birds which actually DO sound exactly like the clocks, and the hummingbirds are so exciting EVERY time you see them (yeah, I'm a bird nut). Even though you're a 15 minute leisurely walk from the most excellent village, Cortona, Villa Rosa seems to be in the middle of nowhere, far indeed from the madding crowd. You could hear a pin drop at night, all the better to hunt fireflies... Italy gets pretty hot in the summer, especially the afternoon, so when it's siesta time I recommend closing all of the villa's shutters nice and tight, which creates a wonderful cocoon of dark coolness... perfect for sleep after eating lunch outside at the huge table (if you're smart much of your time in Italy will be spent eating). I've been here twice already, and it is a place that manages to suck out ALL of your real-life stresses with its Italian panache, in a way that makes you wonder why you were so stressed in the first place. Do yourself a favour, and wallow in the loveliness that is Villa Rosa in the perfect little pocket of civilization called Cortona.

13 Reviews

from £338 / night

£2,365 / week

Holiday apartment rental

Farinaio apartment

2 bedrooms • 1 bathroom • sleeps 4

from £108 / night

£756 / week

Farinaio holiday apartment rental

Farinaio apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £118 / night

£829 / week

Holiday farmhouse with swimming pool in Farinaio

Farinaio farmhouse

4 bedrooms • 2 bathrooms • sleeps 9

3 Reviews

from £170 / night

£1,098 - £1,398 / week

Holiday apartment rental

Centoia apartment

1 bedroom • 1 bathroom • sleeps 3

11 Reviews

from £94 / night

£652 / week

Holiday farmhouse with golf nearby in Fratticciola

Fratticciola farmhouse

13 bedrooms • 16 bathrooms • sleeps 29

from £718 / night

£4,618 - £7,685 / week

Holiday apartment with shared pool in Cortona

Cortona apartment

1 bedroom • 1 bathroom • sleeps 2

from £82 / night

£570 / week

Holiday villa in Mercatale di Cortona

Mercatale di Cortona villa

4 bedrooms • 3 bathrooms • sleeps 10

10 Reviews

from £207 / night

£1,443 / week

Holiday lodge in Cortona

Cortona lodge

1 bedroom • 1 bathroom • sleeps 4

2 Reviews

from £79 / night

£551 / week

Cortona holiday apartment rental

Cortona apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £82 / night

£573 / week

Holiday villa with swimming pool in Cortona

Cortona villa

7 bedrooms • 5 bathrooms • sleeps 14

3 Reviews

from £333 / night

£2,327 / week

Holiday apartment in Cortona

Cortona apartment

1 bedroom • 1 bathroom • sleeps 3

10 Reviews

from £71 / night

£455 / week

Holiday apartment in Cortona

Cortona apartment

2 bedrooms • 1 bathroom • sleeps 5

4 Reviews

from £102 / night

£714 - £1,249 / week

Holiday home with swimming pool in Cortona

Cortona house

2 bedrooms • 2 bathrooms • sleeps 5

6 Reviews

from £338 / night

£2,365 / week

Apartment rental in Ruffignano

Ruffignano apartment

2 bedrooms • 2 bathrooms • sleeps 5

12 Reviews

from £154 / night

£1,021 - £1,754 / week

Holiday villa in Cortona

Cortona villa

2 bedrooms • 2 bathrooms • sleeps 5

“Paradise!” Had a one week stay at Villa Rosa and fell in love with the house, the gardens and Cortona. This really is a peice of Italian paradise - the house is beautifully appointed...spacious, modern but still a taste of Italian living. IT was the best 7 days :0)

14 Reviews

from £338 / night

£2,365 / week

Cortona holiday b&b rental

Cortona b&b

11 bedrooms • 11 bathrooms • sleeps 22

2 Reviews

from £821 / night

£5,131 / week

Cortona holiday home rental

Cortona house

2 bedrooms • 2 bathrooms • sleeps 4

44 Reviews

from £99 / night

£532 - £670 / week

Holiday apartment in Cortona

Cortona apartment

1 bedroom • 1 bathroom • sleeps 2

from £103 / night

£719 / week

Holiday apartment with shared pool in Fratta Santa Caterina

Fratta Santa Caterina apartment

1 bedroom • 1 bathroom • sleeps 2

from £55 / night

£378 - £665 / week

Montanare holiday farmhouse rental

Montanare farmhouse

6 bedrooms • 8 bathrooms • sleeps 16

2 Reviews

from £77 / night

£462 - £2,473 / week

Holiday villa with swimming pool in Cortona

Cortona villa

4 bedrooms • 3 bathrooms • sleeps 10

2 Reviews

from £360 / night

£2,519 / week

Cortona holiday apartment rental

Cortona apartment

1 bedroom • 1 bathroom • sleeps 4

“A great, beautiful, convenient stay in Cortona” This was our favorite place we stayed during a month in Italy. Vanna is so wonderfully gracious and friendly. The whole town of Cortona is like a medieval/renaissance fairy tale. There is plenty to do just within walking distance of this beautiful apartment. We did not have a car, but spent an incredible leisurely week as pedestrians in the area. Can't wait to return, and will definitely stay here again!

29 Reviews

from £117 / night

£632 - £841 / week

Home rental in Cortona with shared pool

Cortona house

3 bedrooms • 3 bathrooms • sleeps 6

1 Reviews

from £329 / night

£2,290 / week

Cortona holiday apartment rental

Cortona apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £120 / night

£847 - £996 / week

Holiday villa with swimming pool in Cortona

Cortona villa

7 bedrooms • 7 bathrooms • sleeps 14

from £282 / night

£1,972 - £3,520 / week

Holiday apartment with swimming pool in Mercatale di Cortona

Mercatale di Cortona apartment

2 bedrooms • 1 bathroom • sleeps 4

1 Reviews

from £123 / night

£857 / week

Cortona holiday apartment rental

Cortona apartment

3 bedrooms • 2 bathrooms • sleeps 6

3 Reviews

from £153 / night

£907 - £1,321 / week

Holiday apartment with shared pool in Cortona

Cortona apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £106 / night

£740 - £937 / week

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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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