Cycling holiday villas and apartments Cortona | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Bagnolo (2)
  • Capezzine (2)
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  • Centoia (6)
  • Farinaio (4)
  • Fratta Santa Caterina (8)
  • Fratticciola (1)
  • Mercatale di Cortona (6)
  • Montalla (4)
  • Montanare (5)
  • Montecchio (6)
  • Poggioni (1)
  • Ruffignano (1)
  • Teverina (2)

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166 Holiday homes

Filters applied: Cycling holidays (166)

(2) Excellent 

1 / 20

Ca de Muito, a peaceful Tuscan cottage with breathtaking views and a private outdoor pool - Mercatale di Cortona cottage sleeps 6

Cortona / Mercatale di Cortona

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 20 km; Swimming pool; Child friendly ;
Charming Ca de Muito has an idyllic position on the Tuscany side of the Niccone Valley. The views of the stunning countryside are breath-taking, they stretch over the Niccone Valley including 2 picturesque castles, to the village of Preggio on the opposite hillside. W  …see more

from £146 / night

£1021 / week

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from £146 / night

1 / 84

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

Cortona / Montecchio

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: 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 £116 / night

£812 - £941 / week

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from £116 / night

(1) Very Good 

1 / 22

Villino Laura - Montecchio villa sleeps 4

Cortona / Montecchio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: 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 £134 / night

£778 - £1112 / week

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from £134 / night

1 / 89

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

Cortona / Montecchio

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: 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

£135 - £941 / week

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from £20 / night

1 / 18

Rustic two bedroom Tuscan apartment close to Cortona's main square, wifi and parking available - Cortona apartment sleeps 2

Province of Arezzo / Cortona

2 2 1 night min stay

  • 2 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Ask owner if suitable for children;
Quintani Sole - central apartmentApartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square a  …see more

from £69 / night

£428 / week

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from £69 / night

(2) Very Good 

1 / 24

Idyllic Tuscan villa with annexes, outdoor pool an - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 140 km; Swimming pool; Child friendly ;
Villa Le Contesse sleeps 6+2 people in three bedrooms with three bathrooms and another four people in two annexes (Serenella & Limonaia), each with it's own living room, kitchenette bathroom and bedroom. It nestles in the immediate out skirts of Cortona, one of the many  …see more

from £231 / night

£1616 - £1958 / week

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from £231 / night

1 / 17

Province of Arezzo / Cortona

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
 …see more

from £65 / night

£436 - £496 / week

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from £65 / night

1 / 21

Peschino - Teverina villa sleeps 12

Cortona / Teverina

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Casa Peschino sits on the lower slopes of a quiet side valley, with stunning and extensive views over the green countryside of woods, vineyards, olive groves and farmland. It is reached by a short track through fields of sunflowers, wild flowers, maize and tobacco plant  …see more

from £246 / night

£1720 - £2708 / week

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from £246 / night

1 / 7

LA TESA Olivo - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: 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

£471 / week

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from £35 / night

1 / 16

Province of Arezzo / Cortona

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
 …see more

from £56 / night

£368 - £428 / week

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from £56 / night

1 / 30

1 bedroom sleeps 4, beautiful view - Cortona house sleeps 4

Province of Arezzo / Cortona

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 15 km; Suitable for children age 5+; Car advised;
A beautiful and comfortable typical Cortona country farmhouse. This nice accommodation is situated 5 minutes by car far from the historic hill town of Cortona. The house is over a hundred years old and constructed of local river rock, the walls are up to a meter thick.  …see more

from £65 / night

£342 / week

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from £65 / night

(8) Excellent 

1 / 35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

Province of Arezzo / Cortona

7 24 3 nights min stay

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min stay
Key info: Nearest beach 250 km; Swimming pool; Child friendly ;
Villa Nobile is a stunning 19th Century classical style villa recently restored authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land. A private avenue of young cypresses bringing you to our doorstep. Tran  …see more

from £65 / night

£471 / week

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from £65 / night

1 / 8

La Tesa Girasole - Farinaio apartment sleeps 4

Cortona / Farinaio

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
The apartment Girasole is situated on the ground floor and it has a separate entrance. It consists of: a living room, a kitchen, two bedrooms, two bathrooms with shower and independent heating.Apartment cleaning, detergents and waste:We use non-toxic cleaning products a  …see more

from £35 / night

£684 / week

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from £35 / night

1 / 10

Grecale - PI2012_226 - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 3 7 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: 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

£385 - £677 / week

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from £55 / night

1 / 13

Cortona / Montecchio

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Child friendly ; Pet friendly;
 …see more

from £127 / night

£889 - £1556 / week

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from £127 / night

1 / 7

Appartamento in Sant' Angelo di Cortona - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Apartment Sant' Angelo in Cortona is a bright and spacious one bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in typical Tuscan style, full of character, offering guests a warm vacation home.The ap  …see more

from £86 / night

£599 / week

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from £86 / night

1 / 12

Quintani Luna - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Ask owner if suitable for children;
QUINTANI LUNAApartment for 2 person, compose by one bedroom + kitchen + 1 bathroom with shower. WIFI, TV, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square and grocery.THE HISTORICAL BUILD  …see more

from £69 / night

£428 / week

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from £69 / night

(1) Excellent 

1 / 10

ETRUSCA - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
Dopo il positivo riscontro per le Mura Etrusche, Gian Luca e Lucia hanno il piacere di proporvi una nuova struttura, Etrusca.La casa, situata nel centro storico di Cortona, lungo Via Nazionale detta "Ruga Piana", strada principale, che unisce Piazza della  …see more

from £79 / night

£556 / week

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from £79 / night

(31) Excellent 

1 / 21

Tuscan Villa. Borgo Valecchie. Cortona - Montanare villa sleeps 10

Cortona / Montanare

4 10 5 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min stay
Key info: 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 £201 / night

£1411 - £2522 / week

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from £201 / night

1 / 11

Beautiful four bedroom Tuscan villa with private pool and garden - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Fonte Vecchia is a beautifully restored, spacious luxury Tuscany villa for rent with a dramatic watch tower, lying among gentle hills enjoying views unchanged for centuries. Centuries ago, when the church was the significant power in this area, most of the local nobili  …see more

from £328 / night

£2295 - £4195 / week

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from £328 / night

(1) Excellent 

1 / 24

Il Moro Novo - Montalla apartment sleeps 3

Cortona / Montalla

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
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 village, so i  …see more

from £60 / night

£314 - £593 / week

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from £60 / night

(2) Excellent 

1 / 21

Villa Cicaleta within walking distance to Cortona - Cortona farmhouse sleeps 7

Province of Arezzo / Cortona

3 7 7 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 8 km; Swimming pool;
Surrounded by olive groves and a 3000sqm private garden, the fenced-in holiday villa offers absolute peace and quiet at only 1,5 kilometres from the Etruscan Cortona, which can be easily reached on foot. The Trasimeno lake with its nice beaches and islands is at 8km and  …see more

from £147 / night

£1026 - £1667 / week

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from £147 / night

1 / 16

Tuscan hideaway: charming rural villa with pool and spectacular views, sleeps 4 - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
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 spectacular  …see more

from £93 / night

£648 - £977 / week

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from £93 / night

(3) Excellent 

1 / 21

Tuscan Family Villa Castiglioni, Pool easy access - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 26 km; Swimming pool; Child friendly ;
This exceptional, luxurious and impeccable private estate in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Extraordinary views of both the famed Montechio Castle and, the Eternal Tuscan hill town of Castiglion Fiorentino can be easily  …see more

from £458 / night

£3200 - £4334 / week

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from £458 / night

1 / 23

Ville Alto: peaceful Tuscan villa in the Cortona countryside - Montanare villa sleeps 8

Cortona / Montanare

4 8 3 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Suitable for children age 5+; Car advised; Ask about pets;
We restored this house 25 years ago. Is a lovely and peaceful house to stay in contact with the nature. You also have at close distance so many places to visit, the Trasimeno lake, Florence, Perugia, Pienza, Montefiascone, Città della Pieve, Gubbio, Assisi, Siena (one  …see more

from £154 / night

£812 - £1180 / week

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from £154 / night

(2) Excellent 

1 / 10

Province of Arezzo / Cortona

2 5 4 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min stay
Key info: Child friendly ; No pets allowed; Private garden;
 …see more

from £86 / night

£599 - £1048 / week

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from £86 / night

(3) Excellent 

1 / 30

Poggiobello - Cortona cottage sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
The cottage is immersed in the splendid countryside with breathtaking views all around. It is surrounded by the lovelyundulating hills covered with sunflowers, olive groves and cypresses, you will find yourself totally immersed in an enchanted atmosphere frozen in time.  …see more

Pricing unknown

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1 / 19

Agriturismo Pilari - Mercatale di Cortona farmhouse sleeps 4

Cortona / Mercatale di Cortona

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: 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 £129 / night

£727 / week

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from £129 / night

1 / 55

Casa dei Colori - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; No pets allowed;
The apartment consists of living room with a convertible sofa-bed, kitchen, bathroom with shower, bidet, sink and toilette connected to a separate room with washer machine. Bedroom with queen size bed and wardrobe/closet. The house has been completely renovated in 2011,  …see more

from £71 / night

£428 - £753 / week

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from £71 / night

1 / 12

appartment in old court yard in Cortona, Arezzo - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
nice apartment made of hall with sofa bed, kitchen with dishwasher micro wave and electric oven, washing machine, one bed-room and bathroom with shower and air conditioning system. The apartment is part of an ancient court yard among Tuscany's hills. The property i  …see more

from £52 / night

£342 / week

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from £52 / night

(2) Excellent 

1 / 12

Charming Cortona villa with private pool (Dardano) - Cortona villa sleeps 6

Province of Arezzo / Cortona

4 6 7 nights min stay

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Dardano is a deceptively large house, full of atmosphere. It is a simple country home, basic even, but with an elemental charm. You drive up to the house with its ancient stone well and to one side there's a little vine-covered area for shady outdoor eating. The garde  …see more

from £165 / night

£1150 / week

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from £165 / night

(1) Excellent 

1 / 12

Large Tuscan farmhouse apartment in beautiful Cortona countryside, four bedrooms, pool access - Cortona farmhouse sleeps 6

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
The apartment is independent, and has beautiful piece of ancient furniture own heating system, some of them has a fire-place. This has a own outside space and very well fitted out with garden furniture, all equipped with every thing necessary to be efficient and functi  …see more

Pricing unknown

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(12) Excellent 

1 / 21

Rustic Tuscan farmhouse in the town of Cortona with gorgeous views, swimming pool, private garden and barbecue - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

5 8 7 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Swimming pool;
This charming Tuscan Farmhouse is set in a lovely, unspoilt region near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields. Casa Al Campo has 2 acres of unfenced land including its own private vineyard, two terraces and plenty of shaded seating  …see more

from £212 / night

£1479 - £3248 / week

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from £212 / night

1 / 27

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £85 / night

£556 - £812 / week

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from £85 / night

(2) Excellent 

1 / 38

Province of Arezzo / Cortona

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Child friendly ; Car advised; Air conditioning;
 …see more

from £60 / night

£419 / week

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from £60 / night

(5) Excellent 

1 / 24

Gorgeous five bedroom villa, game room, outdoor p - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
The Cortonese hillside, La Fortezza and the ancient wall which encloses the town, dominate the view of the surrounding hillside.Guests have exclusive use of the delightful 12x6 swimming pool, with Roman steps, which lies in an extremely panoramic position and from where  …see more

from £143 / night

£1000 - £3112 / week

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from £143 / night

1 / 9

Il Borgo Agritourism - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: 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 £171 / night

£1026 / week

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from £171 / night

(1) Excellent 

1 / 83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 18 km; Swimming pool; Child friendly ;
 …see more

from £86 / night

£513 - £838 / week

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from £86 / night

(1) Excellent 

1 / 24

The Old Tavern of Casale Il Granaio - Cortona studio sleeps 2

Province of Arezzo / Cortona

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Child friendly ;
Welcome to Casale Il Granaio, a magic place in the heart of Valdichiana.In the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno lake and in the middle between the cities of Arezzo and Perugia. From here is easy also to reach Montepulciano, Siena, Pienz  …see more

from £63 / night

£350 - £436 / week

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from £63 / night

1 / 20

Province of Arezzo / Cortona

6 12 1 night min stay

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £56 / night

£385 / week

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from £56 / night

Top Destination reviews

To Stones
Amazing Home Away From Home

The best first impression was to be greeted late at night by Ester and her partner in the dark and in poor weather just so we could find a parking spot and get situated in the property. Ester was amazing and has gone to great lengths to ensure her ho … see more
villa ai cedri
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 really friendly and helpful any time you need somethin … see more
Stunning Tuscan villa with five bedrooms, private
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 character making this place a unforgettable experience. The garden … see more

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