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)
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  • Mercatale di Cortona (3)
  • Montanare (3)
  • Montecchio (1)
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69 Holiday homes

Filters applied: Water sports (69)

(8) Excellent 

1 / 35

Villa Nobile is a stunning 19th Century Villa

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

£475 / week

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from £65 / night

1 / 15

Casa Carina - Montecchio - San Lorenzo cottage sleeps 2

Cortona / Montecchio, San Lorenzo

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Car advised;
Casa Carina is a cozy detached cottage with chestnut beams, terracotta tiles, and views towards Cortona and the surrounding countryside, with shared swimming pool (open June to September). Set amongst working farmland, and in the Summer surrounded by fields of sunflowe  …see more

from £69 / night

£432 - £539 / week

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from £69 / night

1 / 89

Querce/luxury. Private village. 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

£136 - £949 / week

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from £20 / 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 / 12

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

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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(1) Excellent 

1 / 6

Province of Arezzo / Cortona

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car advised; Pet friendly;
 …see more

from £87 / night

£475 / week

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from £87 / 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

£432 - £561 / week

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from £65 / night

(2) Excellent 

1 / 23

Tuscan holiday farmhouse villa features stunning grounds and pool, 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 ;
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 £104 / night

£690 - £776 / week

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from £104 / night

1 / 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
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 / 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 £87 / night

£604 / week

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from £87 / 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 £61 / night

£388 / week

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from £61 / 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) Excellent 

1 / 24

Newly restored two bedroom apartment in beautiful

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 £117 / night

£819 / week

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from £117 / night

(8) Excellent 

1 / 55

Il Bocciolo 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 £69 / night

£453 - £582 / week

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from £69 / night

(2) Very Good 

1 / 59

Charming 2 bedroom apartment in restored Tuscan farmhouse with pool located in historic Cortona

Cortona / Centoia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: 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 £95 / night

£651 - £992 / week

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from £95 / 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

£345 / week

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from £65 / night

(1) Very Good 

1 / 10

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

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

Pricing unknown

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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

£863 - £1207 / week

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from £69 / night

1 / 7

Le Volpaie - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Child friendly ; Car essential; Pet friendly;
Our home is located 6 miles outside of Cortona, on the Tuscan/Umbrian border, near Lake Trasimeno. The house dates back to the 1700s and was originally a farmhouse. It is set a third of the way up the hill, below a forest and we have over a hundred acres in which you ca  …see more

from £243 / night

£1700 / week

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from £243 / night

1 / 12

appartment in old court yard in Cortona, Arezzo

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

£345 / week

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from £52 / night

(1) Excellent 

1 / 31

ANTICO PALLAIO - Cortona villa sleeps 9

Province of Arezzo / Cortona

3 9 3 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min stay
Key info: 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 £259 / night

£1725 / week

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from £259 / night

1 / 7

Casale del Gabbiano - large villa near Cortona

Cortona / Centoia

9 18 Min stay varies

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

from £700 / night

£4900 - £5880 / week

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from £700 / night

(8) Very Good 

1 / 20

Tuscan villa with private pool and garden and breathtaking countryside views

Cortona / Mercatale di Cortona

4 10 7 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 23 km; Swimming pool; Child friendly ;
Casaccia is a beautiful medieval house on a hilltop with a large private pool and gardens offering incredible views. Fully refurbished, the villa offers 4 large bedrooms (sleeping up to 10), and three bathrooms, including a delightful cottage in the garden with its own  …see more

from £122 / night

£849 - £1999 / week

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from £122 / 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 £203 / night

£1423 - £2544 / week

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from £203 / night

1 / 42

Casa Fiordaliso - Cortona house sleeps 4

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 9 km; Child friendly ; Car advised;
Casa indipendente, con uno stupefacente panorama. Potrete mangiare all'aperto gustando la bellezza della Valdichiana e di Cortona, sfondo su cui si staglia la figura del Palazzone, villa principesca del 1500 con la sua torre ed il suo muro merlato.In assoluta privacy,  …see more

from £80 / night

£561 - £733 / week

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from £80 / 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) 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 £87 / night

£518 - £845 / week

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from £87 / night

(12) Excellent 

1 / 21

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

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 £214 / night

£1492 - £3276 / week

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from £214 / night

(2) Excellent 

1 / 21

Villa Cicaleta within walking distance to Cortona

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 £148 / night

£1035 - £1682 / week

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from £148 / night

(1) Excellent 

1 / 22

House in Central Cortona with Private Garden

Province of Arezzo / Cortona

1 6 3 nights min stay

  • 1 bedroom
  • Sleeps 6
  • 3 nights min stay
Key info: 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 £69 / night

£483 / week

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from £69 / night

(1) Excellent 

1 / 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
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 / 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 £57 / night

£371 - £432 / week

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from £57 / night

1 / 24

Cortona / Mercatale di Cortona

5 11 4 nights min stay

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 12 km; Swimming pool;
 …see more

from £194 / night

£1294 / week

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from £194 / night

(8) Excellent 

1 / 38

Tuscan Dream|Private|Pool|Walk to Cortona|FreeWiFi

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;
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

(1) Excellent 

1 / 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
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 £50 / night

£390 - £523 / week

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from £50 / 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 £57 / night

£388 / week

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from £57 / night

(4) Excellent 

1 / 30

Tuscany, Cortona - Villa Under The Sun - Gorgeous

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;
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

1 / 15

Casa Le Celle - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

4 8 2 nights min stay

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

from £259 / night

£1552 / week

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from £259 / night

(9) Excellent 

1 / 33

Villa Rosa - Heaven in Tuscany|Pool|WiFi|Cortona

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;
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

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

Top Destination reviews

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
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
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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