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Filters applied: Cycling holidays (146)

32 of 146 Results

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from £328 / night

£2295 - £4195 / week

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1 / 11

Cortona holiday villa rental

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

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from £328 / night

£2295 - £4195 / week

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Fonte Vecchia is Situated Deep in the Heart of Piero della Francesca Country in the Niccone Valley and is rated one of the top 15 villas to stay in Italy  …see more

from £68 / night

£475 - £792 / week

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1 / 22

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 6

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

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from £68 / night

£475 - £792 / week

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The villa "Meridiana" is very easy to reach, is settled in the quiet Brolio Tuscany village Villa with private garden and private swimming pool Tennis table in garden. Fenced private garden. Ground floor 2-3 days a week stays the owner in order to take care to the garden and swimming pool.  …see more

from £88 / night

£612 - £900 / week

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1 / 22

Holiday villa rental

Province of Arezzo / Cortona

Villa / 2 Bedrooms / sleeps 4

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner

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from £88 / night

£612 - £900 / week

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The Orangery, charming villa with private swimming pool is placed in the magnificent Tuscan countryside, surrounded by olive trees and vineyard: the perfect setting in an atmosphere of complete relaxation and comfort but also only 400 mt far from the stunning Cortona  …see more

Featured properties

from £124 / night

£864 - £1713 / week

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1 / 19

Cortona holiday villa rental

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

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Not on the map

from £124 / night

£864 - £1713 / week

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it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

from £299 / night

£2087 - £3058 / week

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1 / 25

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

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from £299 / night

£2087 - £3058 / week

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The Villa is placed in the beautiful and striking Tuscan countryside, surrounded by olive trees and vineyard:the perfect setting to indulge in the colours and scents of our valley for a complete relaxation and comfort with breathtaking views, only 400mt far from Cortona  …see more

from £257 / night

£1799 - £2518 / week

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1 / 20

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 5 Bedrooms / sleeps 15

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

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from £257 / night

£1799 - £2518 / week

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Luxurious detached villa with private pool in southern Tuscany near Cortona. Panoramic and quiet location. 5 bedrooms, 11 bed places + 2 double sofa beds. Air conditioning and Wi-fi internet connection.  …see more

from £96 / night

£670 - £1184 / week

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(1) Excellent 5/5 

1 / 18

Cortona holiday villa rental

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 16

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £96 / night

£670 - £1184 / week

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Casale Ginezzo is beautiful independent Villa, located 15 km from Cortona, in the heart of the cortonese mountains, immersed into the green woods of oak and chestnut trees. From the big garden you can enjoy the charming and unspoilt natural environment  …see more

from £300 / night

£2100 - £3700 / week

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(1) Excellent 5/5 

1 / 20

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 16

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

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Not on the map

from £300 / night

£2100 - £3700 / week

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Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

from £50 / night

£350 / week

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(8) Very Good 4.5/5 

1 / 16

Cortona holiday apartment rental

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 2

  • Nearest beach 7 km
  • Not suitable for children
  • Car essential
  • No pets allowed

Very Good 4.5/5 

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from £50 / night

£350 / week

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Fifteen minutes walk to Cortona on a private path with exceptional views, the stone-house is secluded, and restored and furnished with taste. Surrounded by garden terraces on various levels, and well provided with garden furniture for outdoor meals and relaxation. SEPTEMBER OFFER: £250 for 5 or 7 nights. Gourmet-meals under request.  …see more

from £175 / night

£1224 - £1648 / week

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(2) Very Good 4.5/5 

1 / 23

Holiday villa in Cortona

Province of Arezzo / Cortona

Villa / 3 Bedrooms / sleeps 6

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £175 / night

£1224 - £1648 / week

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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.  …see more

from £48 / night

£331 - £2875 / week

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(3) Excellent 5/5 

1 / 14

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 7 Bedrooms / sleeps 24

  • Nearest beach 250 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning

Excellent 5/5 

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from £48 / night

£331 - £2875 / week

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Villa Nobile is a stunning 19th Century classical villa recently restored farmhouse 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. Private, Tranquil, Perfect for large get togethers or for small families. Perfect for Children of all ages  …see more

from £100 / night

£699 - £2199 / week

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(4) Excellent 5/5 

1 / 20

Holiday villa in Mercatale di Cortona

Cortona / Mercatale di Cortona

Villa / 4 Bedrooms / sleeps 10

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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from £100 / night

£699 - £2199 / week

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Beautiful 800 year-old hilltop villa with stunning views , 4 bedrooms (sleeps 10) and private 12m x 6m pool. On border of Tuscany and Umbria, perfect for exploring local area. Fully restored, the house exudes character. ideal for large groups and families.  …see more

from £88 / night

£612 - £1259 / week

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(8) Excellent 5/5 

1 / 21

Apartment rental in Ruffignano with swimming pool

Cortona / Ruffignano

Apartment / 2 Bedrooms / sleeps 5

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

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Not on the map

from £88 / night

£612 - £1259 / week

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A tranquil haven in which to recharge the batteries. Poolside relaxation with cultural visits. Great hill walking at the summit of one of Tuscany's toughest cycling hill climbs. Comfort of our family-friendly cottage-style apartment, set high above the Tiber valley. Good sightseeing and great restaurants at nearby Cortona.  …see more

from £76 / night

£529 - £1123 / week

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(19) Excellent 5/5 

1 / 16

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 2 Bedrooms / sleeps 4

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner

Excellent 5/5 

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from £76 / night

£529 - £1123 / week

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"Perfect for half terms holidays - without any increase in the general rate" . 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.  …see more

from £175 / night

£1224 - £2483 / week

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(11) Excellent 5/5 

1 / 21

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

Farmhouse / 5 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £175 / night

£1224 - £2483 / week

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This charming Tuscan Farmhouse with a new salt water pool is ideal for family holidays as it is tucked away in a large garden in lovely, unspoilt Southern Tuscany near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields.  …see more

from £190 / night

£1328 - £1770 / week

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(5) Excellent 5/5 

1 / 21

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 7

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £190 / night

£1328 - £1770 / week

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This is a place to enjoy an authentic Tuscan experience. Close to the historic town of Cortona and set in acres of olives and pastures - this beautiful 17th century newly renovated Mill House with private pool has been painstakingly restored.  …see more

from £370 / night

£2590 - £3508 / week

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(3) Excellent 5/5 

1 / 19

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 12

  • Nearest beach 26 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £370 / night

£2590 - £3508 / week

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The Villa is set along a sun soaked hill where the garden extends into pretty olive groves. The property is in a quiet location and yet so easy to explore the Tuscan and Umbria treasures  …see more

from £180 / night

£1259 - £2015 / week

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(15) Excellent 5/5 

1 / 20

Holiday home rental

Cortona / Montanare

House / 4 Bedrooms / sleeps 10

  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

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from £180 / night

£1259 - £2015 / week

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Tuscany property in a old village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome. 30 minutes from the highway and 10 from the train station.  …see more

from £57 / night

£396 - £554 / week

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(7) Excellent 5/5 

1 / 24

Home rental in Montecchio, San Lorenzo with swimming pool

Cortona / Montecchio, San Lorenzo

House / 2 Bedrooms / sleeps 4

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £57 / night

£396 - £554 / week

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"Il Villino di Cortona", is a cozy house nestled in the heart of val di chiana: in an area rich in history and cultural attractions. Tuscany holiday house. (exclusive use property, house, pool, garden). The veranda is ideal to enjoy a rich and tasty breakfast, or to immerse yourself in the reading a good book.  …see more

from £118 / night

£824 - £1544 / week

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(1) Good 3/5 

1 / 20

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Good 3/5 

Add to shortlist

from £118 / night

£824 - £1544 / week

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Villa Gloria is a quaint cottage that is set in a charming and panoramic position, with completely authentic surroundings. Immersed in the lush mountains of Cortona, near the border between Tuscany and Umbria  …see more

from £300 / night

£2100 - £3954 / week

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1 / 16

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 5 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Add to shortlist

from £300 / night

£2100 - £3954 / week

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Villa Torre degli Elci is set in the greens of the Tuscan countryside, midst olives and cypress trees and just 4 km from Cortona. The name of the Villa derives from the old sighting tower which has testimonials from 13th and 14th century and which became a monastery  …see more

from £136 / night

£947 - £1490 / week

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1 / 18

Cortona holiday villa rental

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 14

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £136 / night

£947 - £1490 / week

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Casa Delia is an antique villa which lies at the bottom of a green hill of Cortona in a quiet and panoramic position. The villa is surrounded by a big park, partly shaded by trees, and with its beautiful swimming pool looks onto the Chiana valley and Cortona  …see more

from £96 / night

£670 - £1799 / week

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1 / 14

Holiday villa with swimming pool in Poggioni

Cortona / Poggioni

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £96 / night

£670 - £1799 / week

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Il Biancospino is a gracious property ideal for families and small groups, immersed in the greens of the cortonese mountains between oak and chestnut trees.  …see more

from £119 / night

£828 - £1849 / week

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1 / 16

Cortona holiday villa rental

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £119 / night

£828 - £1849 / week

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Villa Maria Laura rises in panoramic position, dipped in the green and tranquility of the cortonesian hills, ideal for all of those who wish to enjoy the beauty and tranquility which this place can offer.  …see more

from £412 / night

£2878 - £3598 / week

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1 / 20

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 8 Bedrooms / sleeps 17

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Add to shortlist

from £412 / night

£2878 - £3598 / week

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The property Villa il Trebbio is an antique palace close to Cortona which dates back to the 16th century. The farmhouse in stone has been personally furnished by the owner with antique family pieces and reflects a simple and at the same time elegant atmosphere  …see more

from £93 / night

£648 - £1439 / week

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1 / 18

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome

Add to shortlist

from £93 / night

£648 - £1439 / week

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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 £96 / night

£670 - £1184 / week

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1 / 16

Bagnolo holiday villa rental

Cortona / Bagnolo

Villa / 2 Bedrooms / sleeps 4

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £96 / night

£670 - £1184 / week

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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 £162 / night

£1134 - £2572 / week

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1 / 20

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 9

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Add to shortlist

from £162 / night

£1134 - £2572 / week

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Villa le Corchie is a charming villa located in a quiet and panoramic position in one of the most scenic areas of the hills surrounding Cortona.  …see more

from £89 / night

£619 - £1259 / week

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1 / 16

Bagnolo holiday villa rental

Cortona / Bagnolo

Villa / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £89 / night

£619 - £1259 / week

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Nice property comprising several stone buildings situated in panoramic location on the hills around Cortona, at 750 m above-sea-level. This property is surrounded by beautiful woods and valleys and offers extensive views.  …see more

from £103 / night

£720 - £1439 / week

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1 / 16

Cortona holiday villa rental

Province of Arezzo / Cortona

Villa / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Add to shortlist

from £103 / night

£720 - £1439 / week

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The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.  …see more

from £237 / night

£1655 - £2983 / week

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1 / 18

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Add to shortlist

from £237 / night

£1655 - £2983 / week

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Lovingly restored in 2004 Villa Orlando sleeps 8 people comfortably with four bedrooms, all with en-suite bathrooms with showers. This villa is perfect for families or groups that like to spend time enjoying the outdoors.  …see more

from £47 / night

£324 - £570 / week

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1 / 10

Cortona holiday apartment rental

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 3

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Add to shortlist

from £47 / night

£324 - £570 / week

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Beautifulapartment with swimming pool situated in the vicinity of Cortona, Tuscany.  …see more

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