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Family Friendly Holidays in Cortona - Holiday Lettings

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2,668 family friendly properties

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Holiday apartment with shared pool in Fratta Santa Caterina

Fratta Santa Caterina apartment

1 bedroom • 1 bathroom • sleeps 4

from £63 / night

£436 - £790 / week

1 / 19

Holiday villa with swimming pool in Cortona

Cortona villa

4 bedrooms • 5 bathrooms • sleeps 8

from £538 / night

£1,465 - £3,077 / week

1 / 26

Holiday farmhouse with swimming pool in Creti

Creti farmhouse

6 bedrooms • 5 bathrooms • sleeps 14

from £349 / night

£2,443 - £3,714 / week

1 / 57

Cortona holiday cottage rental

Cortona cottage

3 bedrooms • 3 bathrooms • sleeps 8

from £160 / night

£1,121 / week

1 / 51

Holiday apartment with shared pool in Fratta Santa Caterina

Fratta Santa Caterina apartment

1 bedroom • 1 bathroom • sleeps 2

from £60 / night

£413 - £733 / week

1 / 19

Holiday villa rental

Montecchio villa

6 bedrooms • 4 bathrooms • sleeps 12

from £280 / night

£1,955 - £3,420 / week

1 / 26

Cortona holiday villa rental

Cortona villa

4 bedrooms • 5 bathrooms • sleeps 8

from £210 / night

£1,465 - £3,077 / week

1 / 31

Holiday cottage with shared pool in Cortona

Cortona cottage

2 bedrooms • 1 bathroom • sleeps 4

from £137 / night

£956 / week

1 / 24

Cottage rental in Pietraia with swimming pool

Pietraia cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £119 / night

£831 - £1,955 / week

1 / 29

Holiday villa with swimming pool in Cortona

Cortona villa

5 bedrooms • 5 bathrooms • sleeps 11

from £210 / night

£1,466 - £3,078 / week

1 / 19

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.

from £338 / night

£2,365 / week

1 / 71

Holiday farmhouse with swimming pool in Farinaio

Farinaio farmhouse

4 bedrooms • 2 bathrooms • sleeps 9

from £147 / night

£929 - £1,271 / week

1 / 26

Holiday apartment rental

Centoia apartment

1 bedroom • 1 bathroom • sleeps 3

from £88 / night

£615 / week

1 / 46

Holiday lodge in Cortona

Cortona lodge

1 bedroom • 1 bathroom • sleeps 4

from £78 / night

£569 - £667 / week

1 / 27

Holiday villa with swimming pool in Cortona

Cortona villa

7 bedrooms • 5 bathrooms • sleeps 14

from £328 / night

£3,111 - £4,872 / week

1 / 36

Holiday apartment in Cortona

Cortona apartment

2 bedrooms • 1 bathroom • sleeps 5

from £98 / night

£684 - £1,197 / week

1 / 10

Holiday home with swimming pool in Cortona

Cortona house

2 bedrooms • 2 bathrooms • sleeps 5

from £338 / night

£2,365 / week

1 / 72

Apartment rental in Ruffignano

Ruffignano apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £147 / night

£971 - £1,668 / week

1 / 19

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)

from £338 / night

£2,365 / week

1 / 53

Cortona holiday home rental

Cortona house

2 bedrooms • 2 bathrooms • sleeps 4

from £98 / night

£528 - £665 / week

1 / 16

Montanare holiday farmhouse rental

Montanare farmhouse

6 bedrooms • 8 bathrooms • sleeps 16

from £74 / night

£440 - £2,352 / week

1 / 14

Holiday villa with swimming pool in Cortona

Cortona villa

4 bedrooms • 3 bathrooms • sleeps 10

from £367 / night

£2,565 / week

1 / 17

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!

from £116 / night

£629 - £837 / week

1 / 33

Home rental in Cortona with shared pool

Cortona house

3 bedrooms • 3 bathrooms • sleeps 6

from £340 / night

£2,307 / week

1 / 8

Cortona holiday apartment rental

Cortona apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £118 / night

£831 - £977 / week

1 / 26

Holiday villa with swimming pool in Cortona

Cortona villa

7 bedrooms • 7 bathrooms • sleeps 14

from £281 / night

£1,967 - £3,511 / week

1 / 32

Holiday apartment with swimming pool in Mercatale di Cortona

Mercatale di Cortona apartment

2 bedrooms • 1 bathroom • sleeps 4

from £118 / night

£820 / week

1 / 12

Cortona holiday apartment rental

Cortona apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £152 / night

£899 - £1,310 / week

1 / 53

Holiday apartment with shared pool in Cortona

Cortona apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £105 / night

£733 - £929 / week

1 / 21

Holiday cottage rental

Cortona cottage

3 bedrooms • 2 bathrooms • sleeps 9

from £127 / night

£888 / week

1 / 62

Montalla holiday home let

Montalla house

4 bedrooms • 2 bathrooms • sleeps 8

from £279 / night

£1,952 / week

1 / 15

Cortona holiday lodge rental

Cortona lodge

1 bedroom • 1 bathroom • sleeps 4

from £78 / night

£569 - £667 / week

1 / 27

Holiday villa in Cortona

Cortona villa

6 bedrooms • 8 bathrooms • sleeps 14

from £384 / night

£2,684 / week

1 / 34

Lodge letting in Cortona with shared pool

Cortona lodge

1 bedroom • 1 bathroom • sleeps 4

from £78 / night

£569 - £667 / week

1 / 27

Cortona holiday apartment rental

Cortona apartment

1 bedroom • 1 bathroom • sleeps 3

from £77 / night

£537 - £771 / week

1 / 10

Holiday apartment with shared pool in Fratta Santa Caterina

Fratta Santa Caterina apartment

1 bedroom • 1 bathroom • sleeps 4

from £60 / night

£413 - £733 / week

1 / 16

Villa rental in Cortona with swimming pool

Cortona villa

2 bedrooms • 2 bathrooms • sleeps 4

from £118 / night

£684 - £880 / week

1 / 25

Holiday villa with swimming pool in Cortona

Cortona villa

6 bedrooms • 8 bathrooms • sleeps 15

from £733 / night

£5,130 / week

1 / 39

Montalla holiday farmhouse rental

Montalla farmhouse

6 bedrooms • 4 bathrooms • sleeps 14

from £313 / night

£1,657 - £2,990 / week

1 / 35

Holiday home with shared pool in Montecchio

Montecchio house

2 bedrooms • 1 bathroom • sleeps 5

from £147 / night

£683 / week

1 / 35

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