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

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4,303 Holiday homes

(7) Excellent 

13

Holiday villa accommodation

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 15 km
  • Child friendly

from £55 / night

£380 - £760 / week

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from £55 / night

(54) Excellent 

23

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

from £80 / night

£528 - £704 / week

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Responds fast!
avg. 2 hours 48 minutes

from £80 / night

(8) Excellent 

26

Holiday villa rental

Cortona / Montecchio

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £252 / night

£1,759 - £3,077 / week

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from £252 / night

(43) Excellent 

Certificate of Excellence

35

Holiday villa rental

Cortona / Montanare

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £168 / night

£1,322 - £2,599 / week

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Responds fast!
avg. 58 minutes

from £168 / night

45

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £70 / night

£485 / week

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from £70 / night

29

Cottage rental in Pietraia with swimming pool

Cortona / Pietraia

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £107 / night

£749 - £1,762 / week

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from £107 / night

(2) Excellent 

27

Holiday lodge in Cortona

Province of Arezzo / Cortona

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £70 / night

£484 - £572 / week

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Responds fast!
avg. 1 hour 19 minutes

from £70 / night

22

Holiday apartment in Montecchio

Cortona / Montecchio

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Nearest beach 15 km
  • Child friendly
  • Pet friendly

from £44 / night

£265 / week

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from £44 / night

(1) Excellent 

42

Holiday cottage rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £114 / night

£794 / week

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Responds fast!
avg. 1 hour 17 minutes

from £114 / night

(1) Excellent 

19

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool

from £60 / night

£450 - £490 / week

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from £60 / night

(1) Excellent 

24

Apartment rental in Montalla with shared pool

Cortona / Montalla

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £62 / night

£323 - £515 / week

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Responds fast!
avg. 2 hours 43 minutes

from £62 / 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

from £132 / night

£1,055 / week

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from £132 / night

42

Farinaio holiday apartment rental

Cortona / Farinaio

2 4 2 nights min

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

from £101 / night

£704 / week

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from £101 / night

(28) Excellent 

33

Cortona holiday apartment rental

Province of Arezzo / Cortona

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child friendly
“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!

from £77 / night

£373 - £771 / week

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from £77 / night

(1) Very Good 

22

Holiday villa rental

Cortona / Montecchio

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 155 km
  • Swimming pool
  • Child friendly

from £115 / night

£800 - £1,143 / week

Enquire View

from £115 / night

(8) Excellent 

20

Cortona holiday townhouse accommodation

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £53 / night

£317 - £422 / week

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Responds fast!
avg. 54 minutes

from £53 / night

(6) Excellent 

24

Holiday home with shared pool in Cegliolo

Cortona / Cegliolo

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly

from £106 / night

£660 / week

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from £106 / night

(39) Excellent 

Certificate of Excellence

16

Cortona holiday home rental

Province of Arezzo / Cortona

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 150 km
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £66 / night

£379 - £714 / week

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Responds fast!
avg. 2 hours 2 minutes

from £66 / night

(14) Excellent 

57

Holiday cottage with swimming pool 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
“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.

from £270 / night

£1,890 / week

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Responds fast!
avg. 3 hours 38 minutes

from £270 / 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

from £189 / night

£1,322 - £2,203 / week

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from £189 / night

(1) Excellent 

20

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

2 3 min stay varies

  • 2 bedrooms
  • sleeps 3
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool

from £58 / night

£430 - £490 / week

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from £58 / night

57

Holiday farmhouse with swimming pool in Creti

Cortona / Creti

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £315 / night

£2,203 - £3,348 / week

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from £315 / night

(3) Very Good 

19

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool

from £64 / night

£480 - £590 / week

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from £64 / night

(11) Very Good 

46

Holiday apartment rental

Cortona / Centoia

1 3 4 nights min

  • 1 bedroom
  • sleeps 3
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool

from £73 / night

£484 / week

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Responds fast!
avg. 1 hour 59 minutes

from £73 / night

(3) Excellent 

10

Holiday apartment in Cortona

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden

from £88 / night

£614 - £1,075 / week

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from £88 / night

26

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly

from £106 / night

£748 / week

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from £106 / night

(28) Excellent 

35

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £226 / night

£1,583 - £2,550 / week

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from £226 / night

27

Cortona holiday lodge rental

Province of Arezzo / Cortona

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £70 / night

£396 - £572 / week

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Responds fast!
avg. 1 hour 19 minutes

from £70 / night

(6) Very Good 

51

Apartment accommodation in Montalla with shared pool

Cortona / Montalla

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly

from £135 / night

£727 - £876 / week

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Responds fast!
avg. 2 hours 43 minutes

from £135 / night

(11) Very Good 

18

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies

from £58 / night

£352 - £422 / week

Book View

from £58 / night

15

Holiday villa in Cortona

Province of Arezzo / Cortona

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £101 / night

£616 / week

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from £101 / night

(6) Excellent 

27

Cortona holiday cottage rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £123 / night

£856 / week

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Responds fast!
avg. 1 hour 17 minutes

from £123 / night

(2) Excellent 

17

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £315 / night

£2,200 / week

Book View

from £315 / night

(1) Excellent 

30

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Child friendly
  • Air conditioning

from £132 / night

£616 - £967 / week

Book View

from £132 / night

(1) Very Good 

27

Lodge letting in Cortona with shared pool

Province of Arezzo / Cortona

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £70 / night

£484 - £572 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £70 / night

(2) Average 

37

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning

from £88 / night

£660 - £748 / week

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from £88 / night

16

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Suitable for children age 5+

from £72 / night

£500 / week

Book View

from £72 / night

(1) Average 

33

Cortona holiday apartment rental

Province of Arezzo / Cortona

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Pet friendly
  • Private garden

from £86 / night

£599 / week

Book View

from £86 / night

(1) Excellent 

15

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 5 5 nights min

  • 2 bedrooms
  • sleeps 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £194 / night

£1,357 / week

Book View

from £194 / night

(1) Excellent 

36

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 19 km
  • Swimming pool
  • Child friendly

from £277 / night

£1,937 / week

Book View

from £277 / night

Top Destination reviews

LE MURA ETRUSCHE
Excellent

Wonderful way to relax. Beautiful home with everything you need for a relaxing holiday . House is situated high in the old town, the views are amazing. The hosts were very helpful and kind. … see more
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 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
Villa il Giuggiolo - Azienda Fontelunga
Cosy and spacious villa in quiet idyllic location

Michele is a wonderful host. The villa is charming and very big. Its old fashioned and thats part of the charm. 5mins drive from cortona and with access to a lovely pool. Just idyllic and excellent value for money! … see more
CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI
A Gem in Tuscany

The information provided by Cesare at the time of booking was the best we've ever had! On arrival, we were greeted with a very helpful introduction to "our home for the week". It was great having a welcome gift of wine, some delicious home grown plums and their home produced olive oil. La Colonica is set in lovely gardens/grounds. There are so many places to sit and relax. We especially loved the covered outside dining area. When it comes to the house, the two double bedrooms both with en-suites were perfect for us. The beds were very comfortable with really good quality sheets. Though the kitchen was not large, it had everything we needed for the week including good, sharp knives! We enjoyed evenings in the lounge with a good selection of DVDs. Despite temperatures well in the 30s, we had no need to use the airco. The whole house has high ceilings and is pleasantly cool at night. The parking at La Colonica, outside the house, is very convenient. Although close to the local village, the "cottage" was very quiet. Our week at La Colonica was delightful from start to finish. We loved it and look forward to returning.see more