Cycling holiday villas and apartments Cortona | Holiday Lettings

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Cortona

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190 Holiday homes

Filters applied: Cycling holidays

Travellers going to Cortona are booking June dates now. Secure your holiday home today and have the perfect trip.

(34) Excellent 

25

Holiday villa rental

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £200 / night

£1399 - £2500 / week

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from £200 / night

(2) Very Good 

18

Holiday villa in Cortona

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
“Delivered the experience as promised” Both the accomodation and the rental experience were excellent - a lovely property, exactly as promoted, combined with superb, prompt and effective customer service. A great experience overall. Only proviso; the w  …see more

from £182 / night

£1272 - £1941 / week

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from £182 / night

(8) Excellent 

55

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 £64 / night

£424 - £712 / week

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from £64 / night

(12) 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 £218 / night

£1526 - £2458 / week

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from £218 / 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
Villa Fonte is located in an extraordinary panoramic position in the open countryside surrounded by olive trees and other typical Tuscan plants but within walking distance from the famous historical town of Cortona just 400 meters away. The perfect place for a holiday d  …see more

from £406 / night

£2839 - £4407 / week

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from £406 / night

(3) Excellent 

21

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 26 km
  • Swimming pool
  • Child friendly
“Amazing view and the place to recover from the hustle n bustle of life” House that has been lovingly restored by the owners. Great outdoor space for entertainment and just to chill out with one's family. The caretaker family was very helpful. The main  …see more

from £454 / night

£3173 / week

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from £454 / night

(1) Excellent 

14

Home rental in Cortona with shared pool

Province of Arezzo / Cortona

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
An elegant, 17th Century Tuscan Farmhouse in a glorious location among Tuscan and Umbrian hills, only minutes from the beautiful Etruscan walled town of Cortona. Perfect all year round: walk or cycle in the hills, soak at the Thermal Spa, shop in fresh produce marke  …see more

from £212 / night

£1267 - £1606 / week

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from £212 / 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
Started officially as a busines in 1994 but with previous experience of property rental in the precedent 10 years, Agriturismo Fontelunga is now a reference poit for those searching for a true Tuscan experience.W own same of the nicest accommodation in the traditio  …see more

from £136 / night

£724 - £1381 / week

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from £136 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden

 …see more

from £85 / night

£594 - £1039 / week

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from £85 / night

(2) Very Good 

53

Province of Arezzo / Cortona

2 4 3 nights min

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

 …see more

from £77 / night

£534 / week

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from £77 / night

(1) Excellent 

80

Province of Arezzo / Cortona

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 16 km
  • Swimming pool

 …see more

from £102 / night

£678 - £1009 / week

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from £102 / night

16

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

 …see more

from £56 / night

£365 - £424 / week

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from £56 / night

21

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Neri is situated in San Lorenzo in close driving proximity to Cortona. Cortona is an antique Etruscan town which lies in the heart of the Chiana valley. You can even see the town perched on the hill in front of you  …see more

from £110 / night

£763 - £1695 / week

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from £110 / night

16

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
A special hide-away in Tuscany ! Casa Serena is a really charming little house/villa is set in the middle of olive grove and surrounded Tuscan woodland, and provides privacy and serenity for a truly relaxing vacation. During Autumn and winter, there are the spec  …see more

from £99 / night

£691 - £1123 / week

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from £99 / 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 £140 / night

£975 - £2162 / week

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from £140 / 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 £383 / night

£2678 - £3458 / week

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from £383 / night

31

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
Above the wood oven is engraved 1781. Villa Nello was restored in 2001. It develops on three floors, sleeping 8 people, plus a small independent single bedroom with bathroom.  …see more

from £606 / night

£4238 / week

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from £606 / night

(5) Excellent 

24

Holiday villa in Cortona

Province of Arezzo / Cortona

6 16 3 nights min

  • 6 bedrooms
  • Sleeps 16
  • 3 nights min
  • Nearest beach 119 km
  • Child friendly
  • Pet friendly
Villa Giarradea is the perfect choice for all the people want to spend a beautiful vacancy completely immersed in the peace of the Tuscan nature, without give up to the comfort. The Villa is really near to beautiful trekking, but at just 10 minutes by car from Cortona  …see more

from £346 / night

£2421 / week

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from £346 / night

(10) Very Good 

16

Cortona holiday apartment rental

Province of Arezzo / Cortona

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 7 km
  • Private garden
“Our Saviour” For our main family holiday we drove from England to Italy in August 2011. Our pre-booked accommodation was appalling, but this is not a review for them. We needed accommodation quickly to save our holiday and Marie-Claire (the owner of L  …see more

from £50 / night

£350 / week

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from £50 / night

17

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

 …see more

from £64 / night

£433 - £492 / week

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from £64 / 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
This charming independent villa is situated in panoramic position in the Cortonese Mountains above the Etruscan hill town of Cortona. It's ideal location make it easy visit the most renowned historical and art cities of Tuscany and Umbria.  …see more

from £148 / night

£1030 - £1395 / week

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from £148 / 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
Grecale is a part of the beautiful apartment complex, Poggio al Vento. The apartments are located in the same farmstead, which has been tastefully renovated to retain much of the original character and features. Ideal for a couple or a family, the apartments retain a wa  …see more

from £55 / night

£382 - £671 / week

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from £55 / night

(9) Excellent 

18

Province of Arezzo / Cortona

1 3 3 nights min

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

 …see more

from £60 / night

£390 - £424 / week

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from £60 / night

(2) Excellent 

25

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fonte al Vento is a detached villa wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely respect the privacy of  …see more

from £423 / night

£2458 - £4017 / week

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from £423 / 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
Villino Laura is an old mill immersed in the picturesque green Tuscan countryside only few kilometres from Cortona and has been completely restored maintaining its original charm. The furnishing of this property makes it one of a kind for its class, due to its precious  …see more

from £133 / night

£772 - £1102 / week

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from £133 / night

(5) Excellent 

43

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £64 / night

£445 / week

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from £64 / night

(3) Very Good 

59

Apartment accommodation in Centoia with shared pool

Cortona / Centoia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Ideal location for touring Tuscany and Umbria” La stufa is a comfortable and well furnished apartment with ample room for two couples to enjoy their stay. The front bedroom has a nice view of Cortona and the rear bedroom looks out over La Lombarda's l  …see more

from £94 / night

£615 - £1094 / week

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from £94 / night

(1) Excellent 

24

Apartment rental in Montalla with shared pool

Cortona / Montalla

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Equipped with chairs, shades, and beach beds.It has been restored with respect for the original stile and all the furniture are antique, you will have a warm and relaxing feeling when you enter Il Moro Novo.The house is located just outside a small country villa  …see more

from £60 / night

£312 - £588 / week

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from £60 / night

(9) Excellent 

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

from £245 / night

£1645 - £2028 / week

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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
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £60 / night

£419 - £552 / week

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from £60 / night

(1) Excellent 

14

Province of Arezzo / Cortona

2 4 Min stay varies

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

 …see more

from £111 / night

£386 - £564 / week

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from £111 / night

17

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £68 / night

£255 - £386 / week

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from £68 / night

(1) Excellent 

27

Province of Arezzo / Cortona

3 6 Min stay varies

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

 …see more

from £84 / night

£551 / week

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from £84 / 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
Charming stone farmhouse with original features. Perfect for family holidays. Private fenced pool, table tennis and Wifi Beautiful countryside views. Only 2 kilometres from a village with shops and restaurant. Sought after location on the Tuscany-Umbria border.  …see more

from £150 / night

£884 - £1550 / week

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from £150 / night

42

Province of Arezzo / Cortona

3 6 3 nights min

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

 …see more

from £67 / night

£467 / week

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from £67 / 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
Villa Cortona is a beautifully restored luxury tuscan villa with 5 double bedrooms and 6 bathrooms.Each bedroom has its own different style and character and en-suite bathroom with wonderful views.The interior of Villa Cortona is large, bright and spacious,  …see more

from £412 / night

£2882 - £4577 / week

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from £412 / night

11

Cortona / Montanare

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

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
Villa San Martino is set in a delightful position among extensive grounds overlooking the countryside. The swimming pool is surrounded by olive trees and lush gardens. The nearest town is Cortona, famous for its ancient backgrounds, home town of famous painter Luca Sig  …see more

from £144 / night

£1007 - £1992 / week

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from £144 / night

(3) Excellent 

30

Holiday cottage in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“PEACEFUL” Everything you could want from a holiday home in Tuscany. Very clean accommodation. Plenty of kitchen accessories. Air conditioning. Clean pool. Great food prepared by the owner upon request. Pizzas from heaven!  …see more

Pricing unknown

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Pricing unknown

(4) Very Good 

23

Holiday villa with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect!” We loved the place...it was perfect for our family of four. The apartment had every thing we needed or could have wanted. The lavender and the flowers were perfect. The views and the sunsets were exceptional. We walked over a couple r  …see more

from £102 / night

£1102 / week

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from £102 / night