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 (2)
  • Centoia (6)
  • Farinaio (4)
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  • 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)

1 / 24

Villa Fonte - 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 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 £410 / night

£2864 - £4445 / week

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from £410 / night

1 / 12

Province of Arezzo / Cortona

1 2 2 nights min stay

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

from £60 / night

£385 / week

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from £60 / 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

(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 / 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

(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

Cortona / Montanare

1 3 Min stay varies

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

from £60 / night

£385 / week

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from £60 / night

1 / 24

"Il Palazzolo" casa vacanze Mercatale di Cortona - Mercatale di Cortona farmhouse sleeps 10

Cortona / Mercatale di Cortona

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
“Il Palazzolo” is beautifully situated on the border between Tuscany and Umbria, on the road that connects Cortona to Perugia.Originally An ancient monastry, at the end of the 16th century under the Laurenzi family it became a manor house and around about 1750 after  …see more

from £232 / night

£1624 / week

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from £232 / 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) Very Good 

1 / 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
Key info: 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

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1 / 16

Le Casine - Girasole Apartment - Fratta Santa Caterina apartment sleeps 4

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £59 / night

£409 - £552 / week

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from £59 / night

(1) Excellent 

1 / 24

Newly restored two bedroom apartment in beautiful - Capezzine apartment sleeps 7

Cortona / Capezzine

2 7 1 night min stay

  • 2 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Nearest beach 129 km; 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 £116 / night

£812 / week

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from £116 / night

(5) Very Good 

1 / 51

Casa la Bozza, IL Bozzino - Montalla apartment sleeps 6

Cortona / Montalla

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 200 km; Swimming pool; Child friendly ;
THE HOUSE IS SPLIT IN 2 INDEPENDENT APARTMENT OF THE SAME SIZE, BOT WITH A PRIVATE GARDEN, ENTRANCE AND PARKING, WE CAN RENT ONE OF THEM FOR 6+1 OR THE ENTIRE HOUSE FOR 12+2. THE DESCRIPTION BELOW REFERS TO Il Bozzino, the ground floor oneBUT APPLY TO BOTH. PLEASE READ  …see more

from £131 / night

£706 - £1177 / week

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from £131 / 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 / 101

Province of Arezzo / Cortona

10 20 7 nights min stay

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 17 km; Swimming pool;
 …see more

from £513 / night

£3590 - £5642 / week

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from £513 / night

1 / 15

Le Casine - Papavero Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £54 / night

£371 - £495 / week

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from £54 / night

1 / 16

Casina Vereno - Bagnolo villa sleeps 4

Cortona / Bagnolo

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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. The property, with privat  …see more

from £149 / night

£1039 - £1406 / week

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from £149 / night

(1) Excellent 

1 / 17

Villa San Martino - Cortona villa sleeps 10

Province of Arezzo / Cortona

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
A luxury villa with private pool, Villa San Martino is set on a hill, high above the beautiful Niccone Valley on a quiet road, just 3 minutes from local village shops, restaurants and cafes. The position is a typically Tuscan, offering spectacular views from the house,  …see more

from £315 / night

£2200 - £3200 / week

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from £315 / 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 / 4

Villa Sonia, Cortona Tuscany - 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 15 km; Swimming pool; Child friendly ;
Villa Sonia is for sure, a really special property tucked away on the sleepy hillside of Cortona and, just a short distance form the enchanting franciscan monastery of Le Celle. Villa Sonia is perfect for four to 12 guests.This ancient stone farmhouse dates back to the  …see more

from £207 / night

£1445 - £2471 / week

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from £207 / night

(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

(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) Excellent 

1 / 16

Palazzuolo Due - La Limonaia - Capezzine apartment sleeps 6

Cortona / Capezzine

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: 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 £103 / night

£727 / week

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from £103 / night

(5) Very Good 

1 / 44

La Mimosa at La Lombarda - Centoia apartment sleeps 3

Cortona / Centoia

1 3 4 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 118 km; Swimming pool;
La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes i  …see more

from £65 / night

£428 - £471 / week

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from £65 / night

(1) Excellent 

1 / 25

Fonte al Vento:the Villa - Cortona villa sleeps 10

Province of Arezzo / Cortona

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
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 £427 / night

£2479 - £3633 / week

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from £427 / night

(2) Excellent 

1 / 21

Cortona / Cegliolo

9 25 Min stay varies

  • 9 bedrooms
  • Sleeps 25
  • Min stay varies
Key info: Nearest beach 150 km; Swimming pool; Child friendly ;
 …see more

from £86 / night

£428 / week

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from £86 / 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

(34) Excellent 

1 / 25

Il Villino di Cortona (Property at exclusive use) - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 150 km; Swimming pool; Child friendly ;
"Il Villino di Cortona", cosy holiday home nestled in the green heart of the Chiana Valley in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in contact with nature ... "Il Villino di Cortona”, is a small holiday home, nestled in the Va  …see more

from £82 / night

£522 - £736 / week

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from £82 / night

(9) Excellent 

1 / 32

Cortona, Tuscan Retreat, Serene, WiFi, Pool, Bliss - Cortona house sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Swimming pool;
Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close to the amenities but far enough away for privacy, seclusion and relaxation. We would love to welcome you to Villa Rosa w  …see more

from £135 / night

£1645 - £2023 / week

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from £135 / 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

(2) Excellent 

1 / 43

Casabianca Ossaia Cortona Tuscany - Cortona villa sleeps 10

Province of Arezzo / Cortona

4 10 3 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Suitable for children age 5+; Car advised; No pets allowed;
peaceful village in Ossaia, just 5.5 km from Cortona (5-minute drive). The position is strategic, far from main roads and noise of the city - a perfect family-friendly holiday stay home. The villa has been recently restored so it is modern and fully equipped, with free  …see more

from £52 / night

£342 - £701 / week

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from £52 / night

1 / 41

Villa Liliana - 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;
Villa Liliana is perfectly situated to enjoy the spectacular views of our beautiful valley. Villa Liliana sleeps up to 10 people.On the ground floor, a spacious hallway entry foyer leads into a living room and one bedroom with en-suite bathroom. The spacious kitchen, on  …see more

from £297 / night

£2077 - £3543 / week

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from £297 / night

(2) Very Good 

1 / 19

Le Casine - Limone Apartment - Fratta Santa Caterina apartment sleeps 4

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £63 / night

£438 - £600 / week

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from £63 / night

1 / 14

Le Casine - Bugia Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £51 / night

£352 - £466 / week

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from £51 / night

1 / 19

Castiglion Fiorentino - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Car essential;
This generous and luxurious apartment is settled on the ground floor and each bedroom has it's own outside space. The different levels of a few steps gives it a charming feeling of a house without the weight of it. It is comfortable and tastefully furnished with all mod  …see more

from £150 / night

£851 - £1154 / week

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from £150 / 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

1 / 18

GLI ARCHI - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
It 'a beautiful cottage completely restored, was once a barn and a tobacco warehouse. now has 2 bedrooms, a lounge, a kitchen, 2 bathrooms and a dining room that can become an extraordinary study. It has a swimming pool, a large garden, a bocce court, private parki  …see more

from £69 / night

£855 - £1197 / week

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from £69 / night

1 / 18

Villa San Martino - Cortona villa sleeps 7

Province of Arezzo / Cortona

4 7 7 nights min stay

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: 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 £146 / night

£1016 - £2009 / week

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from £146 / night

(1) Excellent 

1 / 24

Beautiful villa with pool and amazing Tuscan view - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: 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, with two lar  …see more

from £416 / night

£2906 - £4616 / week

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from £416 / night

(3) Excellent 

1 / 20

Casale Ruffignano - Cortona villa sleeps 16

Province of Arezzo / Cortona

6 16 7 nights min stay

  • 6 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.Villa Ruffigano dates back to the 16th century and was the centre of an antique farm on which 30 people worked.Guests ca  …see more

from £574 / night

£4018 - £5898 / week

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from £574 / night

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