Watersports holiday villas and apartments Cortona | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Bagnolo (1)
  • Capezzine (1)
  • Centoia (4)
  • Farinaio (1)
  • Fratta Santa Caterina (7)
  • Mercatale di Cortona (3)
  • Montanare (3)
  • Montecchio (1)
  • Montecchio, San Lorenzo (1)

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73 Holiday homes

Filters applied: Water sports (73)

(2) Excellent 

21

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

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
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 £150 / night

£1044 - £1305 / week

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from £150 / night

(5) Very Good 

44

La Mimosa at La Lombarda - Centoia apartment sleeps 3

Cortona / Centoia

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • 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 £66 / night

£435 - £479 / week

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from £66 / night

(1) Very Good 

15

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 25 km
  • Child friendly
  • Car not necessary

 …see more

from £87 / night

£522 - £696 / week

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from £87 / night

(4) Very Good 

23

Casa La Quercia County apt with views and pool - Cortona villa sleeps 6

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £87 / night

£740 - £1131 / week

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from £87 / night

(9) Excellent 

38

Tuscan Dream|Private|Pool|Walk to Cortona|FreeWiFi - Cortona cottage 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
A dream home just for you. We created our home in Cortona with all the essential mod cons. Music, Kitchen, comfy beds, and of course with the essential pool and (FREE) Wi-Fi. Villa Rosa is nestled into the Cortona (Tuscan) hillside with only a few minutes drive to  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

22

Cortona / Bagnolo

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £261 / night

£1000 - £2218 / week

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from £261 / night

(9) Excellent 

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
  • 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 £235 / night

£1645 - £2023 / week

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from £235 / night

(9) Excellent 

33

Villa Rosa - Heaven in Tuscany|Pool|WiFi|Cortona - Cortona villa 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
With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant Cortona. Couples love it, families love it. It is heaven. A two bedroom, two bathrooms, fully furnished beautiful  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(32) Excellent 

24

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

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 £205 / night

£1435 - £2566 / week

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from £205 / night

18

GLI ARCHI - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
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 £70 / night

£870 - £1218 / week

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from £70 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £66 / night

£444 - £505 / week

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from £66 / night

(3) Excellent 

23

Tuscan holiday farmhouse villa features stunning grounds and pool, sleeps 4 - Cortona villa 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
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £87 / night

£609 - £696 / week

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from £87 / 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 £87 / night

£522 - £853 / week

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from £87 / night

(12) Excellent 

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

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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 £215 / night

£1505 - £3305 / week

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from £215 / night

(2) Very Good 

59

Charming 2 bedroom apartment in restored Tuscan farmhouse with pool located in historic Cortona - Centoia apartment sleeps 5

Cortona / Centoia

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
La Lombarda is our charmingly restored traditional 18th century Tuscan farmhouse. La Stufa is a charming two bedroom apartment with wood-beamed ceilings and terracotta floors. There is a comfortable sofa and two armchairs in the lounge, TV, DVD, books, games and videos  …see more

from £96 / night

£657 - £761 / week

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from £96 / night

35

Casa Fontelunga, ancient tuscan villa with pool - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Casa Fontelunga is a lovely country house placed in an enchanted location hillside, between our olive plantation and just a few minutes from the beautiful art city of Cortona, made famous worldwide from the book and movie 'Under the Tuscan Sun'.Privacy and qui  …see more

from £201 / night

£1174 - £1957 / week

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from £201 / night

16

Province of Arezzo / Cortona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £57 / night

£374 - £435 / week

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from £57 / night

(1) Excellent 

19

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

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
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

(8) Excellent 

55

Il Bocciolo at La Lombarda - Centoia apartment sleeps 3

Cortona / Centoia

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • 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 £70 / night

£457 - £500 / week

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from £70 / night

(1) Excellent 

80

Province of Arezzo / Cortona

2 6 1 night min

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

 …see more

from £105 / night

£696 - £1035 / week

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from £105 / night

(2) Very Good 

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
  • 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) Excellent 

20

Le Casine - Lavanda Apartment - Fratta Santa Caterina apartment sleeps 3

Cortona / Fratta Santa Caterina

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • 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 £50 / night

£390 - £523 / week

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from £50 / night

29

Villa Le Contesse - Cortona villa sleeps 20

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Le Contesse is a beautiful independent villa lying on a hillside, a few minutes from the Etruscan town of Cortona. A large park with holm-oaks and secular trees surrounds the villa, which commands a stunning view over the Valdichiana. Le Contesse has been furnishe  …see more

from £560 / night

£3914 - £4348 / week

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from £560 / night

(4) Excellent 

30

Tuscany, Cortona - Villa Under The Sun - Gorgeous - 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
A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool and Wi-Fi connection, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vib  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(2) Excellent 

22

House in Central Cortona with Private Garden - Cortona cottage sleeps 6

Province of Arezzo / Cortona

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Our house is spacious and full of light - a perfect cool retreat after a warm summer day's exploration in Tuscany. Great for two love birds or a couple with a child, this accommodation in Cortona even has its own little walled garden, where you can sit and chat in  …see more

from £70 / night

£487 / week

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from £70 / night

(11) Excellent 

35

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

Province of Arezzo / Cortona

7 24 3 nights min

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min
  • 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 £66 / night

£479 / week

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from £66 / night

(3) Very Good 

24

The Cypress apt in view CASA COUNTY swimming pool - Cortona farmhouse sleeps 6

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £114 / night

£740 - £957 / week

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from £114 / night

(1) Excellent 

17

Villa San Martino - Cortona villa sleeps 10

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 / week

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from £315 / night

(1) Excellent 

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
  • 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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Pricing unknown

(3) Excellent 

21

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

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • 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 £466 / night

£3256 - £4409 / week

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from £466 / night

(1) Excellent 

31

ANTICO PALLAIO - Cortona villa sleeps 9

Province of Arezzo / Cortona

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. beatiful wiew over the chiana valley. all the old charme of tuscany. 4bedroom, 4 bathroomLocated in the village of Ossaia ( 3 km from Cortona), the property  …see more

from £261 / night

£1740 / week

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from £261 / night

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
  • 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

19

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

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
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

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
  • 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

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
  • 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

7

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

Province of Arezzo / Cortona

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £87 / night

£609 / week

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from £87 / night

(8) Excellent 

30

Fantastic 5 bedroom Tuscan farmhouse with panoramic views and swimming pool - Cortona farmhouse sleeps 16

Province of Arezzo / Cortona

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £348 / night

£2609 - £3479 / week

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from £348 / 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

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

£137 - £957 / week

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from £20 / night

(5) Excellent 

24

Villa Giarradea - Cortona villa sleeps 14

Province of Arezzo / Cortona

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 150 km
  • Child friendly
  • Pet friendly
The Agriturismo Villa Giarradea is a magnificent mansion builded at the end of 600. Completely renovated keeping the original external appearance (the villa is protected by the "Italian fine arts"), the structure is immersed in the green countryside of Cortona. Giarrade  …see more

from £58 / night

£402 / week

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from £58 / night

Top Destination reviews

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
Charming Cottage Near Cortona, Garden, AC,WiFI
A Gem in Tuscany

The information provided by Cesare at the time of booking was the best we've ever had! On arrival, we were greeted with a very helpful introduction to "our home for the week". It was great having a welcome gift of wine, some delicious home grown plum … see more
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

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