Villas with a pool Cortona | Apartments to rent with swimming facilities | Holiday Lettings

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455 Holiday homes

Filters applied: Swimming pool

(36) 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 £264 / night

£1711 - £2588 / week

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Responds fast!
avg. 33 minutes

from £264 / night

(4) Excellent 

23

Holiday villa in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic cottage with beautiful view and surround” Good location and beautiful villages around the cottage. We also loved the view and the pool. The surround of the cottage was very tidy.
…see more

from £106 / night

£790 / week

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Responds fast!
avg. 2 hours 53 minutes

from £106 / 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 £189 / night

£1316 - £2193 / week

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from £189 / 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 £502 / night

£3509 - £5000 / week

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from £502 / night

(39) Excellent 

23

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • 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
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from £115 / night

£702 - £965 / week

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Responds fast!
avg. 1 hour 21 minutes

from £115 / night

(3) Very Good 

42

Holiday apartment with shared pool in Montalla

Cortona / Montalla

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly

from £141 / night

£750 - £1429 / week

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Responds fast!
avg. 2 hours 3 minutes

from £141 / 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 £189 / night

£1321 / week

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from £189 / night

(9) Excellent 

57

Holiday apartment in Centoia

Cortona / Centoia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Great base for discovering Tuscany.” Peter and Nina's apartments are in an ideal situation for exploring Tuscany with the added bonus of a pool to relax by when you return from trips to the surrounding hilltop villages. Il Boccolio is spacious and
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from £71 / night

£483 - £737 / week

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Responds fast!
avg. 2 hours 43 minutes

from £71 / 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

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from £245 / 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 £153 / night

£1066 - £1443 / week

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from £153 / 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

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from £245 / 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

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Responds fast!
avg. 1 hour 15 minutes

from £160 / 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

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from £245 / 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 £702 / night

£3509 / week

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from £702 / 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 £101 / night

£702 - £1053 / week

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Responds fast!
avg. 2 hours 52 minutes

from £101 / 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

£571 / week

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from £87 / 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 £571 / night

£3992 / week

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from £571 / 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 £301 / night

£2106 - £3597 / week

Book View

from £301 / night

(1) Excellent 

44

Cortona holiday villa rental

Province of Arezzo / Cortona

3 6 7 nights min

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

from £141 / night

£983 - £1930 / week

Book View

from £141 / 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 £427 / night

£2983 - £4737 / week

Book View

from £427 / 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

£725 - £1208 / week

Book View

Responds fast!
avg. 2 hours 3 minutes

from £135 / 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

(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

(7) Very Good 

Certificate of Excellence

46

Holiday apartment rental

Cortona / Centoia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool

Certificate of Excellence

from £62 / night

£395 - £693 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £62 / night

(1) Excellent 

19

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £123 / night

£400 - £584 / week

Book View

from £123 / night

(2) Excellent 

88

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

from £106 / night

£615 - £1044 / week

Book View

from £106 / night

(5) Very Good 

33

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

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

from £502 / night

£3509 - £4430 / week

Book View

from £502 / 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 £264 / night

£1755 / week

Book View

from £264 / 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 £589 / night

£4123 / week

Book View

from £589 / night

30

Holiday villa in Cortona

Province of Arezzo / Cortona

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £345 / night

£2413 - £3378 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from £345 / night

(9) Excellent 

16

Holiday apartment in Cortona

Province of Arezzo / Cortona

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £36 / night

£246 / week

Book View

Responds fast!
avg. 21 minutes

from £36 / 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 £239 / night

£1667 / week

Book View

from £239 / night

19

Cortona holiday apartment let

Province of Arezzo / Cortona

2 6 Min stay varies

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

from £79 / night

£658 - £878 / week

Book View

from £79 / 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 £203 / night

£1185 - £1974 / week

Book View

Responds fast!
avg. 2 hours 3 minutes

from £203 / night

18

Cortona holiday b&b rental

Province of Arezzo / Cortona

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from £527 / night

£3509 / week

Book View

from £527 / night

(3) Very Good 

11

Mercatale di Cortona holiday apartment rental

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children age 5+

from £138 / night

£965 / week

Book View

from £138 / 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 £137 / night

£799 - £1141 / week

Enquire View

from £137 / night

(16) 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 £226 / night

£1579 - £2544 / week

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from £226 / 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 £188 / night

£1316 - £2193 / week

Book View

from £188 / 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 £188 / night

£1316 - £2764 / week

Book View

from £188 / night

1