Cycling holiday villas and apartments Cortona

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Bagnolo (2)
  • Capezzine (2)
  • Cegliolo (3)
  • Centoia (6)
  • Farinaio (4)
  • Fratta Santa Caterina (9)
  • Fratticciola (1)
  • Mercatale di Cortona (5)
  • Montalla (4)
  • Montanare (5)
  • Montecchio (10)
  • Montecchio, San Lorenzo (1)
  • Pietraia (1)
  • Poggioni (1)
  • Ruffignano (1)
  • Teverina (2)

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193 Holiday homes

Filters applied: Cycling holidays (193)

20

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

 …see more

from £173 / night

£1121 - £2294 / week

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from £173 / night

19

Agriturismo Pilari - Mercatale di Cortona farmhouse sleeps 4

Cortona / Mercatale di Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
Pilari Farm is located in 'Val di Pierle', a small valley between Tuscany and Umbria, not far from Cortona. Pilari Farm is surrounded by beautiful countryside, offering peace and tranquility. You can rediscover the rhythms of nature, immersed in natural surrou  …see more

from £130 / night

£733 / week

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from £130 / night

(1) Very Good 

36

VILLA FRANCESCA Cortona - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Property DescriptionVilla Francesca is a beautiful villa located in the countryside in the green hills on the border between Tuscany and Umbria, a few kilometers from Cortona, a quaint town rich in history and offers shops and services of all kinds. At about 1 km you wi  …see more

from £140 / night

£975 - £1656 / week

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from £140 / night

(1) Excellent 

16

Palazzuolo Due - La Limonaia - Capezzine apartment sleeps 6

Cortona / Capezzine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Capezzine at Palazzuolo Due is the last restoration we started and will be ready to welcome our Guests next May 2013. It has been declared "Historical Monument" Villa Capezzine is situated in the famous community of Cortona (“Under the Tuscan Sun”: h  …see more

from £104 / night

£733 / week

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from £104 / night

65

Garden of Eden : Mulino - nr Cortona & Trasimeno - Cortona cottage sleeps 5

Province of Arezzo / Cortona

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 7 km
  • Swimming pool
  • Child friendly
Mulino Cottage is a detached cottage, set on its own private plot, in the middle of the village. It has a large garden at the back of the cottage, with fantastic views overlooking the hills and the dales, the meadows, the vineyards, the olive groves, peppered with ever  …see more

from £93 / night

£647 - £949 / week

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from £93 / night

89

Querce/luxury. Private village. Sleeps 5 - Montecchio house sleeps 5

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

£136 - £949 / week

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from £20 / night

101

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 17 km
  • Swimming pool

 …see more

from £518 / night

£3621 - £5690 / week

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from £518 / night

42

Province of Arezzo / Cortona

3 6 Min stay varies

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

 …see more

from £69 / night

£475 - £604 / week

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from £69 / night

84

Fienile/luxury. Private village. Sleeps 5 - Montecchio house sleeps 5

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 £117 / night

£819 - £949 / week

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from £117 / night

(16) Excellent 

46

Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views - Cortona house sleeps 10

Province of Arezzo / Cortona

6 10 3 nights min

  • 6 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
I Mandorli is an original Tuscan farmhouse. It has been refurbished using traditional materials and techniques to maintain it's rustic character and help stay cool through the long summer days. In autumn and winter you can relax in the spacious living room, in fr  …see more

from £216 / night

£1294 / week

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from £216 / night

(1) Very Good 

10

One bedroom apartment in classic Tuscan farmhouse, access to shared swimming pool, gardens and lake fishing - Cortona farmhouse sleeps 4

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This apartment has own outside space and very well fitted out with garden furniture, all equipped with every thing necessary to be efficient and functional. 1 bedroom, living room with kitchenette and sofa bed, bathroom with shower.For the people that are fond of fishin  …see more

Pricing unknown

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Pricing unknown

34

Cortona / Montanare

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£388 / week

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from £61 / night

11

Cortona / Montanare

1 3 Min stay varies

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

 …see more

from £61 / night

£388 / week

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from £61 / night

(20) Excellent 

58

Charming Cottage Near Cortona, Garden, AC,WiFI - Cortona house sleeps 4

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Charming small villa in pretty medieval village about 25 minutes from Cortona. The house is set in large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. Very comfortable and really fully equipped. Mint condition. Lovely Garde  …see more

from £95 / night

£604 - £794 / week

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from £95 / night

9

Il Borgo Agritourism - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
The il Borgo Agritourism Complex is near the historic Etruscan city of Cortona. It is in a beautiful country setting amongst olive trees, cypresses and sunflowers in the Chiana Valley. There is a spacious garden and a communal swimming pool. The agritourism complex is e  …see more

from £173 / night

£1035 / week

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from £173 / night

(7) Excellent 

13

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary

 …see more

from £95 / night

£664 / week

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from £95 / night

(3) Very Good 

20

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from £95 / night

£664 / week

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from £95 / night

17

Home Tuscany suite number 2 - Cortona villa sleeps 2

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
72 sq. Meters (775 sq. Ft) This charming 1 bedroom ground floor apartment rentals in Tuscany, has an open living area leading to a covered private terrace with great views of Chiana Valley and Cortona. It has a fully equipped kitchen leading to a double bedroom and a ba  …see more

from £113 / night

£781 - £888 / week

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from £113 / night

15

Casa Le Celle - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Old 13th century farmhouse furnished in style and surrounded by the Tuscan hills at just Km from Cortona and Lake Trasimeno. The property is divided in 4 bedrooms, 2 bathrooms, 2 living rooms, kitchen, and pantry. There is a swimming pool with panoramic terrace, riding  …see more

from £259 / night

£1552 / week

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from £259 / night

25

Casetta i Ciliegi Cortona - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Casetta I Ciliegi is the ideal place for those who wish to spend a vacation far from the busy city life, in close contact with nature. Green woods, rugged hills and cultivated countryside frame this beautiful, small house which is also endowed with a wide, completely fe  …see more

from £72 / night

£500 - £932 / week

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from £72 / night

7

Casale del Gabbiano - large villa near Cortona - Centoia villa sleeps 18

Cortona / Centoia

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Large villa and guest house set in one of the Tuscany's most sought after areas. Wake up each morning to some truly stunning views across Tuscany - some of the best in the region. Relax by the pool with a cool drink, looking over the valley to Montepulciano. Set am  …see more

from £700 / night

£4900 / week

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from £700 / night

24

Cortona / Farinaio

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Private garden

 …see more

from £308 / night

£2156 / week

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from £308 / night

8

La Tesa Grano - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees.Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating e  …see more

from £35 / night

£500 - £742 / week

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from £35 / night

27

Podere Cantalena Cortona - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere Cantalena is an ancient, stone farmhouse recently and wisely restored placed just outside the small hamlet of Cantalena. The old village is set around 15 km far from Cortona and Castiglion Fiorentino, prosperous towns in the lower Valdichiana rich in art and hist  …see more

from £88 / night

£613 - £888 / week

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from £88 / night

4

Province of Arezzo / Cortona

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£388 / week

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from £61 / night

24

Cortona / Montanare

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly

 …see more

from £69 / night

£475 - £518 / week

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from £69 / night

6

Province of Arezzo / Cortona

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £61 / night

£388 / week

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from £61 / night

19

IL CERRO Cortona - Cortona cottage sleeps 8

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Restored carefully to its old splendour this country cottage is composed of the manor house and two dependences one of which is about 70 m. far from the main house. The three houses are comfortably furnished with traditional country antiques. Hidden amongst the wooded s  …see more

from £101 / night

£707 - £992 / week

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from £101 / night

15

Dardano - Montalla house sleeps 8

Cortona / Montalla

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
It's a characteristic middle age tower, it's origins can be leaded up around the year 1000 A.C. (The building is rises nearby the Etruscan town of Cortona). We wanted to give it the name of Dardano by the way the legend tells that this mythological character w  …see more

from £234 / night

£1638 / week

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from £234 / night

29

Fattoria Le Chianacce - La Manna. Cortona - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Set in the verdant hills of the Valdichiana on the border between the Provinces of Arezzo and Siena the Fattoria delle Chianacce is a typical farmhouse built in the last century. These farms produced some of the very best beef and pork in the area and many continue to d  …see more

from £43 / night

£294 - £544 / week

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from £43 / night

8

Province of Arezzo / Cortona

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£388 / week

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from £61 / night

13

Province of Arezzo / Cortona

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from £57 / night

£393 / week

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from £57 / night

31

Fattoria Le Chianacce - Il Balzo. Cortona - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Set in the verdant hills of the Valdichiana on the border between the Provinces of Arezzo and Siena the Fattoria delle Chianacce is a typical farmhouse built in the last century. These farms produced some of the very best beef and pork in the area and many continue to d  …see more

from £39 / night

£268 - £423 / week

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from £39 / night

(1) Excellent 

83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 18 km
  • Swimming pool

 …see more

from £87 / night

£518 - £845 / week

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from £87 / night

17

Cortona Apartment - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
Dive in the pool of our rental house in Tuscany. A villa for your luxury vacation. Beautiful medieval stone hamlet situated in quiet and panoramic position between olive trees and woods of ancient chestnut trees, typical of Tuscany. The rental villa has been recently re  …see more

from £130 / night

£733 / week

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from £130 / night

15

Province of Arezzo / Cortona

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £99 / night

£604 / week

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from £99 / night

95

Cerro-Castagna/luxury. Private village. Sleeps 6 - Montecchio house sleeps 6

Cortona / Montecchio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cerro + Castagna Cottage make up one extremely large apartment with a covered terrace/verandah - seats 6. Not only are there 2 double bedrooms + 2 bathrooms, there are also 2 sitting/dining rooms, each with a fully fitted kitchen, one of which is very large with a firep  …see more

from £111 / night

£776 - £949 / week

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from £111 / night

78

Stalla/luxury, private village, sleeps 2 - Montecchio house sleeps 2

Cortona / Montecchio

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stalla Cottage is an incredibly romantic, detached cottage with one bedroom + 1 bathroom. It opens onto a private garden with ecstatically beautiful views across the valleys that undulate into a depthless abyss of olive groves, orchards, honey fields of yellows, reds an  …see more

from £13 / night

£87 - £604 / week

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from £13 / night

(3) Excellent 

43

Tuscany Private Home In Cortona, WiFi, Pool, Views - Cortona house sleeps 5

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
Villa Rosa is a private home nestled in the hillside of the historic and vibrant hill top town of Cortona. A few minutes drive or a leisurely stroll into the City of Cortona, with expansive views over the valley to the distance shores of Lake Trasimeno Villa Rosa is  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

31

Villa Barbara - Cortona villa sleeps 6

Province of Arezzo / Cortona

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
Villa Barbara is situated on the top of a hill kissed by the sun and caressed by the stars. Skilfully restored to keep its ancient charm untouched, it attracts with its solemn dignity and with its remarkable environmental landscaping. Completely furnished following the  …see more

from £222 / night

£1552 - £1983 / week

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from £222 / night

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