Cortona Villas, Holiday rentals and apartments

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Bagnolo (3)
  • Cantalena (1)
  • Capezzine (2)
  • Cegliolo (5)
  • Centoia (8)
  • Farinaio (5)
  • Fratta Santa Caterina (10)
  • Fratticciola (11)
  • Localita Mucchia (2)
  • Mercatale (7)
  • Mercatale di Cortona (17)
  • Montalla (20)
  • Montanare (10)
  • Montecchio (18)
  • Montecchio, San Lorenzo (1)
  • Pietraia (14)
  • Poggioni (4)
  • Ruffignano (1)
  • Teverina (8)

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732 Holiday homes

1 / 18

Tuscany traditional 3 bedroom farmhouse - Cortona farmhouse sleeps 9

Province of Arezzo / Cortona

3 9 7 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
is a simple but charming 3 bedroom farmhouse sleeping up to 9 people. Outside guests enjoy a private garden and private swimming pool (open from mid May to the end of September each year). Inside it is furnished simply but tastefully in a traditional Tuscan style. It is  …see more

from £157 / night

£1095 - £1495 / week

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from £157 / night

1 / 23

Cortona / Fratta Santa Caterina

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
 …see more

from £171 / night

£1283 / week

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from £171 / night

1 / 16

Province of Arezzo / Cortona

2 4 2 nights min stay

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

from £56 / night

£368 - £428 / week

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from £56 / night

(1) 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

(2) Excellent 

1 / 24

Charming Tuscan Villa with private pool and garden, stunning valley views! - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
A charming cottage situated in dominant position with view of the surrounding hills covered with silver olive groves and the Valdichiana valley. The house lies in a relaxing, peaceful area and is surrounded by a large fenced garden and aromatic plants. In the garden you  …see more

from £89 / night

£616 - £1453 / week

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from £89 / night

(1) Excellent 

1 / 10

ETRUSCA - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 3 1 night min stay

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

from £79 / night

£556 / week

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from £79 / night

1 / 22

Tuscany villa, private pool, for family & group - Mercatale di Cortona farmhouse sleeps 24

Cortona / Mercatale di Cortona

12 24 Min stay varies

  • 12 bedrooms
  • Sleeps 24
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 12 km; Swimming pool;
If you take the road which follows the Tuscan-Umbrian border you come to Pierle, a medieval hamlet in the hills between Cortona and Lake Trasimeno, its castle dominating the verdant valley below.Here surrounded by olive groves and woodland of oaks and chestnuts, you wil  …see more

from £449 / night

£3120 - £5508 / week

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from £449 / night

(1) Excellent 

1 / 14

Province of Arezzo / Cortona

2 4 Min stay varies

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

from £112 / night

£389 - £569 / week

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from £112 / 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 / 7

Casale del Gabbiano - large villa near Cortona - Centoia villa sleeps 18

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 / week

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from £700 / night

(30) 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 / 19

Wonderful traditional Tuscan a - Cortona apartment sleeps 6

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car not necessary;
'Vecchio Frantoio' is a bright and spacious air-conditioned two-bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in the Tuscan manner add to the character of this comfortable and beautiful apart  …see more

from £120 / night

£770 - £1018 / week

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from £120 / night

(3) Very Good 

1 / 11

Splendid flat in Tuscany, pool & breathtaking view - Mercatale di Cortona apartment sleeps 6

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 12 km; Swimming pool; Suitable for children age 5+;
If you take the road which follows the Tuscan-Umbrian border you come to Pierle, a medieval hamlet in the hills between Cortona and Lake Trasimeno, its castle dominating the verdant valley below.Here surrounded by olive groves and woodland of oaks and chestnuts, you wil  …see more

from £107 / night

£642 - £941 / week

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from £107 / night

1 / 14

La Piccionaia - Cortona apartment sleeps 5

Province of Arezzo / Cortona

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
“Le Gelosie apartments” are the natural and inviting alternative to our hospitality and combine good taste and attention for details.The materials, the colours and the spaces were studied to satisfy the esthetical pleasure along with the natural need for comfort. Th  …see more

from £171 / night

£1197 / week

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from £171 / 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 / 12

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

Province of Arezzo / Cortona

4 6 Min stay varies

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

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(2) Excellent 

1 / 10

Province of Arezzo / Cortona

2 5 Min stay varies

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

from £77 / night

£513 - £1048 / week

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from £77 / night

(3) Very Good 

1 / 42

La Bozza , country apartment with private garden - Montalla apartment sleeps 8

Cortona / Montalla

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 200 km; Swimming pool; Child friendly ;
Started officially as a busines in 1994 but with previous experience of property rental in the precedent 10 years, Agriturismo Fontelunga is now a reference poit for those searching for a true Tuscan experience.W own same of the nicest accommodation in the traditional  …see more

from £137 / night

£730 - £1393 / week

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from £137 / night

1 / 19

Cortona / Poggioni

2 4 1 night min stay

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

from £103 / night

£718 / week

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from £103 / 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

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(1) Excellent 

1 / 22

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

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

£479 / week

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from £69 / night

1 / 24

Province of Arezzo / Cortona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
Key info: Beach / lakeside relaxation; Not suitable for children; Car not necessary;
 …see more

from £785 / night

£5495 / week

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from £785 / night

1 / 100

Nina - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Child friendly ;
ExteriorsThis beautiful and secluded villa lies in Cortona’s countryside, with spectacular views over the valley, Cortona and Trasimeno Lake. Located only a couple of minutes from the town center, it is also very close to the most famous art cities in the world, w  …see more

from £220 / night

£1539 / week

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from £220 / night

(3) Excellent 

1 / 24

Cortona / Cegliolo

3 8 1 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £99 / night

£599 / week

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from £99 / 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

(2) Very Good 

1 / 12

Province of Arezzo / Cortona

6 6 Min stay varies

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

from £123 / night

£855 / week

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from £123 / night

1 / 24

Villa Margherita Tre - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
Located in a true oasis of peace and tranquillity, Villa Margherita Tre is a sweet indipendent villa with private pool offering breathtaking views over the hills surrounding the sought after town of Cortona as well as unbeatable value for money. With 2 bedrooms, 2 bathr  …see more

from £35 / night

£240 - £1036 / week

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from £35 / night

1 / 11

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

Province of Arezzo / Cortona

4 8 Min stay varies

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

from £328 / night

£2295 - £4195 / week

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from £328 / night

1 / 100

I Girasoli - 4+2 pax (sup) - Cortona apartment sleeps 6

Province of Arezzo / Cortona

2 6 2 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Nearest beach 130 km; Swimming pool; Child friendly ;
This apartment of 110sq-m hosts up to 6 people on holidays near Cortona. It keeps full Tuscan campigna fashion: wooden beams and terracotta floors. To enter the apartment guests go thorough a porticoed veranda prepared for meals alfresco. Downstairs it features a living  …see more

from £69 / night

£428 - £513 / week

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from £69 / 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 £257 / night

£1539 / week

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from £257 / night

1 / 27

Province of Arezzo / Cortona

3 6 Min stay varies

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

from £85 / night

£556 - £812 / week

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from £85 / night

1 / 101

I Girasoli - 4+2 pax - Cortona apartment sleeps 6

Province of Arezzo / Cortona

2 6 2 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Nearest beach 130 km; Swimming pool; Child friendly ;
This 90sq-m apartment hosting 4+2 (6 guests) near Cortona is perfect to absorb Tuscan lure. It concentrates Tuscan style in its terracotta floor, its wooden ceiling which kept its structure like in the old times. The first thing guests find as they are entering  …see more

from £69 / night

£428 - £471 / week

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from £69 / night

(5) Excellent 

1 / 4

Tranquil villa in Tuscan town of Cortona with private pool, terrace and nearby golf course - Cortona villa sleeps 7

Province of Arezzo / Cortona

4 7 7 nights min stay

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
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 and provides an authentic t  …see more

from £235 / night

£1641 - £2195 / week

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from £235 / night

(9) Excellent 

1 / 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
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 / 100

Residence Valdichiana - 4 pax - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
4 pax This apartment for rent in Tuscany boasts its own private garden. This apartment of the farmhouse can host up to 4 guest. The country style, the typical warmth of Tuscan hospitality make it a perfect place to experience the flavour of Tuscany. This apart  …see more

from £107 / night

£590 - £761 / week

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from £107 / 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 / 30

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

Province of Arezzo / Cortona

1 4 1 night min stay

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

from £65 / night

£342 / week

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from £65 / night

1 / 14

Province of Arezzo / Cortona

3 5 2 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £103 / night

£385 / week

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from £103 / 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

(4) Excellent 

1 / 13

Province of Arezzo / Cortona

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 15 km; Child friendly ; Car advised;
 …see more

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