Cortona apartment or villa with a private pool area | Holiday Lettings

Close

View larger map

Also consider

Europe Holidays
445826 properties
Italy Holidays
103774 properties
Tuscany Holidays
23930 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Montecchio
25 properties
Pietraia
24 properties
Montalla
23 properties
Cignano
15 properties
Mercatale di Cortona
14 properties
Teverina
13 properties
Mercatale
11 properties
Montanare
10 properties
Creti
10 properties
Fratta Santa Caterina
8 properties
Centoia
5 properties
Farinaio
5 properties

Cortona

No dates Enter dates for accurate prices -

Adults, Children

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

260 Holiday homes

Filters applied: Private pool

(35) Excellent 

25

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

from £261 / night

£1696 - £2566 / week

Book View

Responds fast!
avg. 1 hour 41 minutes

from £261 / night

(1) Excellent 

27

Cortona holiday cottage rental

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £87 / night

£566 / week

Book View

from £87 / night

(1) Excellent 

31

Villa rental in Cortona with swimming pool, golf nearby

Province of Arezzo / Cortona

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £261 / night

£1740 / week

Book View

from £261 / night

(7) Excellent 

Certificate of Excellence

30

Holiday home 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
“Spectacular villa in idyllic setting.” Excellent, well-equipped villa in great location with breathtaking views. Structure matches the medieval look of Cortona, but interior has been updated with all the modern conveniences. Very relaxing, convenient
…see more

Certificate of Excellence

from £245 / night

£1645 - £2023 / week

Book View

from £245 / night

(13) Excellent 

Certificate of Excellence

38

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
“Tuscan Dream” I cannot say enough good things about this wonderful Tuscan Dream Villa. The owner Christine was on another continent went out of her way to make us feel at home and cater to our every need through email exchanges and her wonderful hou
…see more

Certificate of Excellence

from £245 / night

£1645 - £2023 / week

Book View

from £245 / night

(14) Excellent 

Certificate of Excellence

32

Holiday home 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
“Fabulous, breathtaking and relaxing - just the right place for a getaway.” The holiday was easy to arrange with good communication on location, directions etc. The villa was lovely and comfortable for our stay. You had the ability to dine inside or
…see more

Certificate of Excellence

from £245 / night

£1645 - £2028 / week

Book View

from £245 / night

(38) 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
“Fabulous stay” Not sure where to start. Michele is one of the most passionate and fantastic villa owners who keeps his focus on customer satisfaction. Right from the moment we landed at the villa until we left, everything was perfectly arranged by
…see more

from £83 / night

£531 - £748 / week

Book View

Responds fast!
avg. 2 hours 14 minutes

from £83 / night

(12) Excellent 

Certificate of Excellence

33

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
“Wonderful Stay” This place turned out to be perfect for me and my wife. It was well located just outside Cortona but a short walking distance to a local cafe and restaurant. It is very private and on a beautiful property with gorgeous views. It has a
…see more

Certificate of Excellence

from £245 / night

£1645 - £2023 / week

Book View

from £245 / night

12

Holiday cottage with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £187 / night

£1305 - £2174 / week

Book View

from £187 / night

16

Cortona holiday villa accommodation

Province of Arezzo / Cortona

2 5 7 nights min

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

from £99 / night

£690 - £1035 / week

Book View

from £99 / night

28

Cortona holiday villa rental

Province of Arezzo / Cortona

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £493 / night

£3449 - £4914 / week

Book View

from £493 / night

18

Holiday villa rental

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly

from £147 / night

£1025 - £2026 / week

Enquire View

from £147 / night

(2) Excellent 

25

Mercatale di Cortona holiday home rental

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 22 km
  • Swimming pool
  • Child friendly

from £160 / night

£926 - £1550 / week

Book View

Responds fast!
avg. 2 hours 51 minutes

from £160 / night

(14) 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
“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 real
…see more

from £224 / night

£1566 - £2522 / week

Book View

from £224 / 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 £106 / night

£740 - £1740 / week

Book View

from £106 / night

(8) 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 - £2199 / week

Book View

Responds fast!
avg. 3 hours 16 minutes

from £122 / night

(1) Excellent 

24

Holiday villa accommodation

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 161 km
  • Swimming pool
  • Child friendly

from £423 / night

£2957 - £4696 / week

Book View

from £423 / night

35

Bagnolo holiday villa rental

Cortona / Bagnolo

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £187 / night

£1309 / week

Book View

from £187 / night

31

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

4 8 7 nights min

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

from £579 / night

£4052 / week

Book View

from £579 / night

(1) Excellent 

27

Holiday villa in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
“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 characte
…see more

from £143 / night

£1000 - £2218 / week

Enquire View

from £143 / night

31

Cortona holiday villa rental

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly

from £187 / night

£1305 - £2740 / week

Book View

from £187 / night

16

Bagnolo holiday villa rental

Cortona / Bagnolo

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £151 / night

£1057 - £1431 / week

Book View

from £151 / night

49

Holiday villa in Cegliolo

Cortona / Cegliolo

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £296 / night

£2069 - £3535 / week

Book View

from £296 / night

38

Cortona holiday villa rental

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £309 / night

£2160 - £3200 / week

Enquire View

from £309 / night

11

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly

from £245 / night

£1714 - £2596 / week

Book View

from £245 / night

(1) Excellent 

27

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 £122 / night

£870 - £1044 / week

Book View

Responds fast!
avg. 2 hours 13 minutes

from £122 / night

35

Cortona holiday villa rental

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £200 / night

£1164 - £1940 / week

Book View

Responds fast!
avg. 2 hours 3 minutes

from £200 / night

(2) Excellent 

4

Holiday farmhouse with swimming pool in Mercatale

Cortona / Mercatale

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Private garden

from £696 / night

£3479 / week

Book View

from £696 / night

(11) Excellent 

35

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

7 24 3 nights min

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min
  • Nearest beach 250 km
  • Swimming pool
  • Child friendly

from £566 / night

£3957 / week

Book View

from £566 / night

15

Montalla holiday home let

Cortona / Montalla

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £237 / night

£1653 / week

Book View

from £237 / night

(1) Excellent 

12

Holiday apartment with swimming pool in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly

from £92 / night

£587 - £783 / week

Book View

from £92 / night

(1) Excellent 

36

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 £302 / night

£2114 - £3605 / week

Book View

from £302 / night

20

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £393 / night

£2747 - £3547 / week

Enquire View

from £393 / 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 £185 / night

£1294 - £2156 / week

Book View

from £185 / night

(11) Excellent 

20

Apartment rental in Ruffignano with swimming pool

Cortona / Ruffignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“An Unforgettable Vacation” We stayed at the Tuscan Idyll in Cortona from mid-May to mid-June of 2014. Kate and Andrew’s home is truly an escape to days gone by. The home is located in the center of Cortona only steps away from all the action. It is be
…see more

from £114 / night

£761 - £1770 / week

Book View

Responds fast!
avg. 3 hours 10 minutes

from £114 / night

(1) Excellent 

28

Holiday villa with swimming pool in Montanare

Cortona / Montanare

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £468 / night

£3276 - £4914 / week

Book View

from £468 / night

24

Holiday villa rental

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £417 / night

£2914 - £4522 / week

Enquire View

from £417 / night

(13) Excellent 

42

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
“Perfect!” This place is special. It’s almost like a time machine. You can easy picture life way back in the old days, but at the same time you have a modern kitchen, pool, nice bathrooms… The house was clean and in good condition. We (family of 5 )
…see more

from £214 / night

£1492 - £3276 / week

Book View

from £214 / night

(2) Excellent 

11

Holiday villa in Cortona

Province of Arezzo / Cortona

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £165 / night

£1150 - £1650 / week

Book View

from £165 / night

20

Holiday villa rental

Province of Arezzo / Cortona

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly

Pricing unknown

Book View

Pricing unknown

1