Cycling holiday villas and apartments Province of Arezzo | Holiday Lettings

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Province of Arezzo

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759 Holiday homes

Filters applied: Cycling holidays (759)

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

(12) Excellent 

40

Holiday villa in Castel San Niccolo

Province of Arezzo / Castel San Niccolo

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children age 5+
“Lovely accommodation, setting and hosts, would go back” I stayed here with my husband and our son and his girlfriend, both in their 20's. The accommodation was absolutely lovely, and our son and his girlfriend had a room which was just next to our ac  …see more

from £90 / night

£627 - £1995 / week

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from £90 / night

(2) Excellent 

16

Province of Arezzo / Chiusi della Verna

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £71 / night

£492 / week

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from £71 / night

(2) Excellent 

21

Holiday farmhouse with swimming pool in Cortona

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
“Stunning views, lovely house, helpful owner.” Cortona is a very picturesque medieval town and this villa is a longish walk from the town itself up a very windy road. The house is only a few years old but built in the style of the old houses. It has la  …see more

from £151 / night

£1053 - £1711 / week

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from £151 / night

(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 £207 / night

£1448 - £2588 / week

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from £207 / night

32

Province of Arezzo / Loro Ciuffenna

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

 …see more

from £37 / night

£255 - £439 / week

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from £37 / night

(24) Excellent 

33

Holiday villa with swimming pool in Poppi

Province of Arezzo / Poppi

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
“Warm welcome, fabulous villa, idyllic setting.” Fantastic welcome from the family. Clean, spacious and full of character. Surrounded by woodland but also great views. On white road about 5km uphill from Poppi, roads a little narrow at times. Pool on  …see more

from £151 / night

£1053 - £2457 / week

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from £151 / night

(1) Excellent 

28

Province of Arezzo / Foiano Della Chiana

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £43 / night

£364 - £548 / week

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from £43 / night

17

Holiday home with shared pool in Foiano Della Chiana

Province of Arezzo / Foiano Della Chiana

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Beautiful country estate situated in the vicinity of Cortona, a charming medieval town in the south of Tuscany, close to the well-known cities full of art of Siena, Arezzo and Perugia. Along with the cottage Rosa dei Venti, the other two farmsteads comprise five apartme  …see more

from £89 / night

£618 - £1202 / week

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from £89 / night

(9) Excellent 

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

from £245 / night

£1645 - £2023 / week

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from £245 / night

24

Castel Focognano holiday villa rental

Province of Arezzo / Castel Focognano

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Relax in Tuscany. The Villa have been renovated with materiaI typical of Tuscany. The pool is open from June to 1 October. A bit further down the villa has a elegant pool, also in a dream Absolutely quiet and even with hot summer enjoying the fresh air of this fantasti  …see more

from £264 / night

£1579 - £3202 / week

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from £264 / night

84

Holiday home in Montecchio

Cortona / Montecchio

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fienile Cottage is a cute detached cottage, situated in its own private garden, with sensational views of olive groves, vineyards, meadows full of sunflowers, poppies and purple cornflowers, spiralling infinitely into the valleys below. It has 1 double bedroom + 1 singl  …see more

from £120 / night

£834 - £965 / week

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from £120 / night

(53) Excellent 

51

Anghiari holiday villa rental

Province of Arezzo / Anghiari

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 66 km
  • Swimming pool
  • Child friendly
“Fantastic Holiday Villa” What can I say about Casa Leana and Tuscany? Well it was just one of the best holidays ever! Starting with the friendly service from Di and Leigh who both met us in Anghiari and took us to the villa so that we didn't get l  …see more

from £248 / night

£1730 - £2630 / week

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from £248 / night

(4) Excellent 

9

Holiday apartment with shared pool in Castel San Niccolo

Province of Arezzo / Castel San Niccolo

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Residence Borgo Caiano: a special place for rural and countryside retreats!<br />Relaxing holiday, vacation and holiday children's families. Swimming and trekking.. a place to feel at home!  …see more

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Pricing unknown

(3) Very Good 

17

Stia holiday apartment rental

Province of Arezzo / Stia

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Casa Teresa is a romantic holiday cottage situated in beautiful and undiscovered corner of Tuscany, the Casentino Valley, between Arezzo and Florence. Enjoy the beauty and peace of the ancient hamlet of Porciano with its stone paved walkways, centuries old church and br  …see more

from £51 / night

£351 - £439 / week

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from £51 / 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 £71 / night

£264 - £400 / week

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from £71 / night

37

Villa rental in Alberoro with shared pool

Province of Arezzo / Alberoro

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
Casa Cicci is a lovely apartment located in an ancient XVIII century rural hamlet, designed by the architect Fossombroni. The complex covers approximately 7 hectares and it is situated on a hill above the Val di Chiana, surrounded by vineyards of the nearby famous wine  …see more

from £101 / night

£636 - £856 / week

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from £101 / night

(3) Very Good 

24

Holiday apartment with shared pool in Chiusi della Verna

Province of Arezzo / Chiusi della Verna

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
wonderful surroundings, inmidst nature, pool, calm, great garden/lawn, perfect place to spend your holidays with a mixture of relax and cultural tripideal for families or group of friendshiking, mountainbiking, relax, silence, nature, sightseeing, cultural events  …see more

from £50 / night

£325 - £483 / week

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from £50 / night

(55) Excellent 

32

Arezzo holiday villa rental

Province of Arezzo / Arezzo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Luxury villa located in the heart of Tuscany with wellness centre, large private park, heated swimming pool and fully stocked wine cellar<br />5 suite and 1 standard bedroom, it can give hospitality up to 12+4 persons. Wi-Fi internet connection.  …see more

from £314 / night

£2193 - £3948 / week

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from £314 / 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 £62 / night

£404 - £439 / week

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from £62 / night

89

Home rental in Montecchio with shared pool

Cortona / Montecchio

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
QUERCE COTTAGE is one of two dwellings in a large cottage, overlooking the private village, Garden Of Eden, the hills, dales, olive groves and vineyards as the vista spirals into a haze of greens, dotted with colours, an infinity of brightly coloured patchwork, against  …see more

from £20 / night

£138 - £965 / week

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from £20 / night

(3) Very Good 

10

Province of Arezzo / Bibbiena

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from £51 / night

£527 / week

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from £51 / night

(2) Excellent 

23

Farmhouse rental in Anghiari with swimming pool

Province of Arezzo / Anghiari

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 133 km
  • Swimming pool
  • Child friendly
Stunning farmhouse close to Anghiari, a spectacular medieval Tuscan town. Private pool, stunning views. For larger groups, there is the option of renting the properties guest house which sleeps a further 6 people.  …see more

from £251 / night

£1755 / week

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from £251 / night

(1) Very Good 

30

Arezzo / Capolona

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £62 / night

£343 - £395 / week

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from £62 / night

28

Holiday apartment rental

Province of Arezzo / Lucignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
Centro storico, attactions/cafes/restaurants right on your doorstep!2 bedroom apartment created from restored medieval olive oil millown garden for alfresco dining/relaxLucignano charming village, great access to all major Tuscan attractionTuscany village holiday<br  …see more

from £73 / night

£465 - £657 / week

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from £73 / night

28

Province of Arezzo / Castiglion Fibocchi

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £27 / night

£185 / week

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from £27 / night

(2) Excellent 

60

Holiday villa with shared pool in Ambra

Province of Arezzo / Ambra

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Fantastic place in the heart of Tuscany.Ideal for relax and to visit Florence, Siena, Arezzo, towns and landscape unique in the world (Chianti, Val d'Orcia) famous for wines, olive oil and cheese. Reacheable by public transport.  …see more

from £88 / night

£615 - £707 / week

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from £88 / 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 £427 / night

£2983 - £4737 / week

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from £427 / night

(6) Excellent 

15

Tower rental in Sansepolcro with shared pool

Province of Arezzo / Sansepolcro

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
Romantic medieval tower. Secluded hideaway in the Tuscan hills. Close to shops, museums, art and culture.  …see more

from £50 / night

£350 / week

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from £50 / night

(1) Excellent 

33

Bibbiena / Casentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £43 / night

£295 / week

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from £43 / night

(2) Excellent 

21

Stia holiday apartment rental

Province of Arezzo / Stia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Appartamento GIRASOLELa Fagiana Holiday Rental is in an optimal position. You will be able to fully enjoy the peace and the quietness of the region as well as being in a good position for numerous outdoor activities, such as horse riding, golf, tennis, mountain  …see more

from £97 / night

£676 - £1229 / week

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from £97 / night

20

Castle rental in Stia

Province of Arezzo / Stia

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about pets
  • Private garden
Medieval Little Guard Tower situated in a beautiful and undiscovered corner of Tuscany, the Casentino Valley, between Arezzo and Florence. Enjoy the beauty and peace of the ancient hamlet of Porciano with its stone paved walkways, centuries old church and breathtaking v  …see more

from £47 / night

£329 - £351 / week

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from £47 / night

21

Apartment rental in Stia with swimming pool

Province of Arezzo / Stia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Appartamento ORCHIDEALa Fagiana Holiday Rental is in an optimal position. You will be able to fully enjoy the peace and the quietness of the region as well as being in a good position for numerous outdoor activities, such as horse riding, golf, tennis, mountain biking,  …see more

from £84 / night

£579 - £1106 / week

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from £84 / 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 £153 / night

£1066 - £1443 / week

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from £153 / 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

(13) Excellent 

12

Holiday cottage in Moncioni

Montevarchi / Moncioni

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning
  • Private garden
If you love walking, peaceful rusticity, organically grown olive oil and all the joys of glorious Tuscany then this cottage is for you! Podere La Rota is a delightful cottage set among peaceful olive groves, barely a ten minute stroll from the village of Moncioni, whic  …see more

from £87 / night

£606 / week

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from £87 / night

17

Apartment rental in Foiano Della Chiana with shared pool

Province of Arezzo / Foiano Della Chiana

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Beautiful country estate situated in the vicinity of Cortona, a charming medieval town in the south of Tuscany, close to the well-known cities full of art of Siena, Arezzo and Perugia. Surrounded by picturesque Tuscan countryside, this property comprises three typical s  …see more

from £70 / night

£485 - £908 / week

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from £70 / night

59

Province of Arezzo / Monte San Savino

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £150 / night

£1404 / week

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from £150 / night

(1) Excellent 

83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £88 / night

£527 - £860 / week

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from £88 / night

(1) Excellent 

27

Holiday villa in Anghiari

Province of Arezzo / Anghiari

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Monterosi has been renovated using traditional Tuscan and ecological material and yet has all the modern comforts. Outside you will find an original pizza oven, two furnished terraces with pergolas for eating al fresco, a private swimming pool and gorgeous garden.  …see more

from £220 / night

£1579 / week

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from £220 / night

79

Cortona / Centoia

2 6 1 night min

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

 …see more

from £106 / night

£702 - £1044 / week

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from £106 / night

Top Destination reviews

Sansepolcro Garden apartment
Revisiting the magic of Sansepolcro

Though this was our first stay at Louise and Franco's wonderful house, it was our third visit to Sansepolcro. The garden apartment was spacious,comfortable and quintessentially Italian and though the March weather didn't lend itself to our using the … see more
Tuscany cottage with Private Pool, BBQ, &amp; Parking
The Trip of a Lifetime!!

This was a beautiful experience! The house was out in the country but not too far away from all of the activities and conveniences. It was beautiful at night! A million stars and so very quiet! It was up on a hill so the view was lovely; vineyar … see more
B&amp;B Casa al Moro, romantic flat in a quaint hamlet
Beautiful tuscan countryside and fantastic family

Cannot rate our stay with Norma and her family highly enough, they looked after us so well, even giving us bread they had baked. The flat is perfect, modern (but keeping with tuscan tradition) and very clean and comfortable with a cooker and a fridge … see more
Grace Hayloft-Il Fienile di Grazia
Utterly Idyllic. We will return

I stayed at the Grace Hayloft - Il Fienile di Grazia with my partner in June and it was indescribably wonderful. The hayloft is basically the most adorable rustic cottage imaginable which was perfect for the 2 of us. There is room to sleep 3 more a … see more
Villa Nava
Fabulous house and pool and very friendly owner

A very large and comfortable house in a lovely location. A huge pool and pretty garden. The owner was very helpful and accommodating and made a stay very relaxing. All rooms have fans, anti mosquitio devices, anti insect curtains A couple of thing … see more
Villa Seccarille
My family and I don't generally go back to places, but this was our second stay at Villa Seccarille and yes, it's a wow.

My family and my parents stayed at Villa Secarille ten years ago and we all finally managed to get back there in August '16. It was even more beautiful than we remembered. We spent 70% of our time at the property as it was a joy, eating together on … see more