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

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

4,313 Holiday homes

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 £323 / night

£2,257 - £3,430 / week

Book View

from £323 / night

31

Cortona holiday villa rental

Province of Arezzo / Cortona

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £259 / night

£1,551 - £3,256 / week

Book View

from £259 / night

(4) Very Good 

24

Holiday cottage with shared pool in Cortona

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £145 / night

£1,013 / week

Book View

from £145 / 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 £258 / night

£1,802 - £3,153 / week

Book View

from £258 / 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

Book View

from £64 / night

(4) Excellent 

39

Cottage rental in Cortona

Province of Arezzo / Cortona

1 6 4 nights min

  • 1 bedroom
  • sleeps 6
  • 4 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £88 / night

£615 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from £88 / night

(12) Excellent 

19

Apartment rental in Ruffignano

Cortona / Ruffignano

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Nearest beach 0 km
  • Child friendly
  • Ask about pets

from £113 / night

£769 - £1,545 / week

Book View

from £113 / 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

Book View

from £60 / 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

Book View

from £58 / 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 £144 / night

£1,006 / week

Book View

Responds fast!
avg. 1 hour 17 minutes

from £144 / 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 £194 / night

£1,356 - £2,260 / week

Book View

from £194 / 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 £110 / night

£768 - £1,806 / week

Book View

from £110 / night

(11) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from £82 / night

£570 / week

Book View

Responds fast!
avg. 1 hour 59 minutes

from £82 / night

26

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £226 / night

£1,351 - £2,837 / week

Book View

from £226 / night

(15) Excellent 

53

Holiday villa 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
“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)

from £285 / night

£1,995 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £285 / night

(1) Excellent 

19

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £259 / night

£1,551 - £3,256 / week

Book View

from £259 / night

35

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min

from £90 / night

£626 / week

Book View

from £90 / night

(3) Excellent 

26

Holiday farmhouse with swimming pool in Farinaio

Cortona / Farinaio

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £145 / night

£1,034 - £1,241 / week

Book View

Responds fast!
avg. 1 hour 15 minutes

from £145 / night

10

Cortona holiday apartment rental

Province of Arezzo / Cortona

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly

from £61 / night

£425 - £714 / week

Enquire View

from £61 / night

(10) Very Good 

20

Holiday villa in Mercatale di Cortona

Cortona / Mercatale di Cortona

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 23 km
  • Swimming pool
  • Child friendly

from £122 / night

£849 - £2,399 / week

Book View

from £122 / 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 £72 / night

£497 - £587 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £72 / night

(14) Excellent 

71

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 £285 / night

£1,995 / week

Book View

Responds fast!
avg. 3 hours 38 minutes

from £285 / night

(3) Excellent 

53

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 6 4 nights min

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

from £124 / night

£672 - £1,385 / week

Book View

Responds fast!
avg. 3 hours 51 minutes

from £124 / 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 £91 / night

£447 - £922 / week

Book View

Responds fast!
avg. 3 hours 51 minutes

from £91 / night

29

Mercatale holiday villa rental

Cortona / Mercatale

6 11 7 nights min

  • 6 bedrooms
  • sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £374 / night

£2,618 - £3,611 / week

Book View

from £374 / night

(1) Excellent 

18

Cortona holiday b&b rental

Province of Arezzo / Cortona

11 20 min stay varies

  • 11 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from £723 / night

£4,519 - £5,423 / week

Book View

from £723 / 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 £72 / night

£497 - £588 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £72 / night

50

Holiday apartment rental

Cortona / Farinaio

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £108 / night

£755 / week

Book View

from £108 / night

(10) Excellent 

18

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies

from £59 / night

£362 - £434 / week

Book View

from £59 / 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

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 £82 / night

£569 / week

Book View

from £82 / 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 £118 / night

£827 / week

Book View

from £118 / 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 £104 / night

£724 - £1,266 / week

Book View

from £104 / night

(2) 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 £325 / night

£2,272 / week

Book View

from £325 / night

(2) Excellent 

30

Holiday villa in Cortona

Province of Arezzo / Cortona

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £389 / night

£2,486 / week

Book View

from £389 / 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 £136 / night

£1,083 / week

Book View

from £136 / 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 £109 / night

£769 - £904 / week

Book View

from £109 / 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 £72 / night

£406 - £586 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £72 / night

(40) 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 £68 / night

£389 - £731 / week

Book View

Responds fast!
avg. 2 hours 2 minutes

from £68 / night

(5) Excellent 

34

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

6 15 3 nights min

  • 6 bedrooms
  • sleeps 15
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £775 / night

£5,426 / week

Book View

Responds fast!
avg. 3 hours 8 minutes

from £775 / night

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 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
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

Also consider