Cycling holiday villas and apartments Cortona | Holiday Lettings

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178 Holiday homes

Filters applied: Cycling holidays

(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 £266 / night

£1726 - £2611 / week

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Responds fast!
avg. 33 minutes

from £266 / 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 £191 / night

£1332 / week

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from £191 / 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

(2) 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

£615 - £1075 / week

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from £88 / 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 £576 / night

£4027 / week

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from £576 / night

16

Farmhouse rental in Cortona with golf nearby

Province of Arezzo / Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

from £58 / night

£378 - £439 / week

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from £58 / 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

(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

£419 - £571 / week

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from £60 / 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 £123 / night

£878 - £1053 / week

Book View

Responds fast!
avg. 2 hours 13 minutes

from £123 / 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

(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. 1 hour 15 minutes

from £160 / night

17

Holiday farmhouse in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

from £66 / night

£448 - £509 / week

Book View

from £66 / 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

(2) Very Good 

53

Holiday apartment accommodation

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets

from £79 / night

£553 / week

Book View

from £79 / night

(38) 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
…see more

from £116 / night

£708 - £974 / week

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Responds fast!
avg. 1 hour 21 minutes

from £116 / 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

£400 - £542 / week

Book View

from £58 / 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

20

Cortona holiday villa rental

Province of Arezzo / Cortona

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

from £176 / night

£1141 - £2509 / week

Book View

from £176 / night

(9) Excellent 

18

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary

from £62 / night

£425 - £443 / week

Book View

Responds fast!
avg. 1 hour 31 minutes

from £62 / night

(15) 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

Book View

from £226 / night

(5) Excellent 

24

Holiday villa in Cortona

Province of Arezzo / Cortona

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 119 km
  • Child friendly
  • Pet friendly

from £143 / night

£1143 - £3046 / week

Book View

from £143 / 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

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 £80 / night

£664 - £885 / week

Book View

from £80 / 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 50 minutes

from £122 / night

(2) 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

£447 - £619 / week

Book View

from £64 / night

21

Holiday villa with swimming pool in Teverina

Cortona / Teverina

6 12 7 nights min

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

from £249 / night

£1740 - £2708 / week

Book View

Responds fast!
avg. 1 hour 15 minutes

from £249 / 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
…see more

from £71 / night

£483 - £737 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £71 / 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 £205 / night

£1195 - £1992 / week

Book View

Responds fast!
avg. 2 hours 3 minutes

from £205 / night

18

Holiday villa with shared pool in Cortona

Province of Arezzo / Cortona

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

from £132 / night

£922 / week

Book View

from £132 / night

(20) Excellent 

58

Holiday home in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
“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 deliciou
…see more

from £111 / night

£620 - £894 / week

Book View

Responds fast!
avg. 1 hour 44 minutes

from £111 / 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

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 £149 / night

£1043 - £2062 / week

Enquire View

from £149 / 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 £115 / night

£768 - £1786 / week

Book View

Responds fast!
avg. 3 hours 10 minutes

from £115 / night

(2) Excellent 

27

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 135 km
  • Swimming pool
  • Child friendly
“Wonderful, true Italian experience"” Have stayed in many hotels and apartments all over the world and this was truly a 'stand-out.' From the moment our group of 8 arrived we were made to feel welcome by Manuela. Little, extra touches such as bruschett
…see more

from £400 / night

£2797 - £3611 / week

Enquire View

from £400 / 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 £145 / night

£1009 - £2237 / week

Enquire View

from £145 / night

(1) 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

£2200 - £3200 / week

Book View

from £315 / night

26

Apartment rental in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £96 / night

£744 - £930 / week

Book View

from £96 / 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 £142 / night

£756 - £1442 / week

Book View

Responds fast!
avg. 2 hours 3 minutes

from £142 / night

(8) Excellent 

30

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

5 16 2 nights min

  • 5 bedrooms
  • Sleeps 16
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Wonderful house, with beautiful views and flexible set up.” The house can in fact be viewed as three separate apartments each with it's own amenities. This gives great flexibility for people to have some quiet time, whether you're travelling with frie
…see more

from £354 / night

£2478 / week

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Responds fast!
avg. 2 hours 53 minutes

from £354 / night

45

Holiday private room rental

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 13 km
  • Child friendly

from £51 / night

£237 - £325 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £51 / night

1