Cortona Villas, Holiday rentals and apartments

Close

View larger map

Price per night

Price per night

to

Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona

Location

  • All locations
  • Bagnolo (4)
  • Cantalena (1)
  • Capezzine (3)
  • Cegliolo (5)
  • Centoia (8)
  • Farinaio (5)
  • Fratta Santa Caterina (10)
  • Fratticciola (12)
  • Localita Mucchia (2)
  • Mercatale (7)
  • Mercatale di Cortona (17)
  • Montalla (11)
  • Montanare (10)
  • Montecchio (12)
  • Montecchio, San Lorenzo (2)
  • Pietraia (8)
  • Poggioni (4)
  • Ruffignano (1)
  • Teverina (6)

More

Less

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Mercatale di Cortona
17 properties
Fratticciola
12 properties
Montalla
12 properties
Montecchio
12 properties
Fratta Santa Caterina
10 properties
Montanare
10 properties
Centoia
8 properties
Pietraia
8 properties
Mercatale
7 properties
Teverina
6 properties
Cegliolo
5 properties
Farinaio
5 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

723 Holiday homes

Travellers going to Cortona are booking August dates now. Secure your holiday home today and have the perfect trip.

(1) Excellent 

1 / 30

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 97 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £369 / night

£2578 - £4397 / week

Enquire Enquire View

from £369 / night

1 / 15

Villa Suardi - Teverina villa sleeps 20

Tuscany / Province of Arezzo / Cortona / Teverina

10 bedroomsSleeps 207 nights min stay

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
This magnificent country house is perfect for a family reunion or a group trip as it has 14 bedrooms. The complex has a large garden with a private swimming pool (12x6 m. Deep from 1.20 to 2.00 m), garden furniture, sunbeds and umbrellas. The main villa is divided in  …see more

from £334 / night

£2334 - £3500 / week

Book Book View

from £334 / night

1 / 20

Tuscany / Province of Arezzo / Cortona

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £370 / night

£2584 - £3413 / week

Enquire Enquire View

from £370 / night

Featured properties

1 / 18

GLI ARCHI - Cortona villa sleeps 4

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 43 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 £67 / night

£834 - £1167 / week

Book Book View

from £67 / night

1 / 19

Agriturismo Poggio del Fabbro - Poggioni villa sleeps 7

Tuscany / Province of Arezzo / Cortona / Poggioni

4 bedroomsSleeps 7Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
L'agriturismo Poggio del Fabbro è situato in località San Pietro a Dame, frazione del comune di Cortona nella montagna cortonese, a 20km dalla città, in una posizione tranquilla e isolata tra le verdi montagne ad un'altezza di 700m slm al confine tra Toscana e Umbria  …see more

from £107 / night

£0 / week

Book Book View

from £107 / night

1 / 16

Palazzo Cinotti Suite Giulio - Cantalena apartment sleeps 2

Tuscany / Province of Arezzo / Cortona / Cantalena

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
Suite Giulio is a beautiful apartment right in the city centre of Siena, between the Cathedral and Piazza Il Campo. Renewed in 2013 offer all the modern comfort, tv sat, wi fi, air conditioned, new bed etc. The aparment is full of light, has frescoes, a big living room  …see more

from £159 / night

£950 / week

Book Book View

from £159 / night

(1) Very Good 

1 / 36

VILLA FRANCESCA Cortona - Cortona villa sleeps 6

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Property DescriptionVilla Francesca is a beautiful villa located in the countryside in the green hills on the border between Tuscany and Umbria, a few kilometers from Cortona, a quaint town rich in history and offers shops and services of all kinds. At about 1 km you wi  …see more

from £135 / night

£942 - £1600 / week

Book Book View

from £135 / night

1 / 44

Tuscany / Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £177 / night

£1238 - £2200 / week

Enquire Enquire View

from £177 / night

1 / 78

Tuscany / Province of Arezzo / Cortona / Centoia

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 16 km; Swimming pool;
 …see more

from £92 / night

£584 - £667 / week

Book Book View

from £92 / night

(4) Very Good 

1 / 23

Renovated Tuscan villa rental with wonderful views and pool

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
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 £84 / night

£917 - £1084 / week

Book Book View

from £84 / night

1 / 14

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £146 / night

£859 - £1034 / week

Book Book View

from £146 / night

1 / 34

Tuscany / Province of Arezzo / Cortona

7 bedroomsSleeps 137 nights min stay

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
 …see more

from £239 / night

£1667 - £3575 / week

Book Book View

from £239 / night

1 / 29

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £159 / night

£1109 - £1209 / week

Book Book View

from £159 / night

1 / 15

Tuscany / Province of Arezzo / Cortona

9 bedroomsSleeps 16Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £239 / night

£1667 - £2917 / week

Book Book View

from £239 / night

(1) Excellent 

1 / 23

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 51 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
 …see more

from £55 / night

£0 / week

Book Book View

from £55 / night

1 / 28

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £182 / night

£1273 - £2069 / week

Enquire Enquire View

from £182 / night

1 / 31

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Pets welcome;
 …see more

from £155 / night

£1084 - £1542 / week

Book Book View

from £155 / night

1 / 27

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £134 / night

£712 - £1186 / week

Book Book View

from £134 / night

1 / 19

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £50 / night

£0 / week

Book Book View

from £50 / night

(1) Excellent 

1 / 24

Stunning Tuscan villa with five bedrooms, private

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 125 km; Swimming pool; Great for children of all ages ;
This imposing two-storey villa is set in stunning grounds, which have the quality of a park. Here you can feel sheltered and secluded in each separate area, including that of the pool. The spaciousness of both the exterior and interior easily accommodates a large group.  …see more

from £124 / night

£863 - £2125 / week

Enquire Enquire View

from £124 / night

1 / 100

Panorama - Cortona villa sleeps 8

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 87 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
ExteriorVilla Panorama is a 17th century farmhouse immersed in an oasis of peace and silence, yet near important and lively cultural centres such as Cortona, Arezzo, Siena and Perugia. From the large panoramic terrace you can admire the beautiful landscape of the Chiana  …see more

from £378 / night

£2642 - £3134 / week

Enquire Enquire View

from £378 / night

1 / 17

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Not suitable for children; No pets allowed;
 …see more

Pricing unknown

Enquire Enquire View

Pricing unknown

(1) Excellent 

1 / 37

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
 …see more

from £167 / night

£959 - £2542 / week

Book Book View

from £167 / night

1 / 20

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
 …see more

from £120 / night

£834 - £1659 / week

Book Book View

from £120 / night

(7) Very Good 

1 / 33

Tuscany / Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £674 / night

£4714 - £6135 / week

Enquire Enquire View

from £674 / night

(2) Excellent 

1 / 24

Six bedroom traditional Tuscan villa in Cortona, a

Tuscany / Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 135 km; Swimming pool; Great for children of all ages ;
With a history dating back to the 17th century, this recently renovated villa distinguishes itself not only by its traditional architectural features and elegant antique furnishings, but above all by its unequalled setting. Perched on the terraced slopes of olive groves  …see more

from £377 / night

£2634 - £3400 / week

Enquire Enquire View

from £377 / night

(5) Excellent 

1 / 20

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car advised;
 …see more

from £42 / night

£250 - £400 / week

Book Book View

from £42 / night

1 / 22

Casa Danielle, Tuscan Retreat - Cortona villa sleeps 4

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 28 km; Swimming pool; Great for children of all ages ;
A lovely home from Home in Tuscany with Private Pool with amazing views A relaxed and comfortable vacation home in the heart of the Tuscan countryside.Just outside the enchanting town of Castiglion Fiorentino near Cortona, Arezzo, Florence, Siena and Perugia is Casa Dan  …see more

from £137 / night

£959 / week

Enquire Enquire View

from £137 / night

(1) Excellent 

1 / 87

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 18 km; Swimming pool; Great for children of all ages ;
 …see more

from £92 / night

£584 - £650 / week

Book Book View

from £92 / night

(1) Excellent 

1 / 24

The Old Tavern of Casale Il Granaio - Cortona studio sleeps 2

Tuscany / Province of Arezzo / Cortona

StudioSleeps 2Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Great for children of all ages ;
Welcome to Casale Il Granaio, a magic place in the heart of Valdichiana.In the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno lake and in the middle between the cities of Arezzo and Perugia. From here is easy also to reach Montepulciano, Siena, Pienz  …see more

from £61 / night

£341 - £425 / week

Book Book View

from £61 / night

(1) Excellent 

1 / 14

Tuscany / Province of Arezzo / Cortona / Montanare

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Not suitable for children; Car advised; No pets allowed;
 …see more

from £417 / night

£584 - £1292 / week

Book Book View

from £417 / night

1 / 15

Cortona walking distance villa - Cortona villa sleeps 5

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
This lovely small villa is located at 400 m from the charming town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. The villa, 65  …see more

from £143 / night

£1000 - £1334 / week

Book Book View

from £143 / night

1 / 19

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car essential; No pets allowed;
 …see more

from £167 / night

£1167 - £1417 / week

Book Book View

from £167 / night

1 / 13

Tuscany / Province of Arezzo / Cortona / Cegliolo

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car advised;
 …see more

from £108 / night

£750 / week

Book Book View

from £108 / night

1 / 24

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £122 / night

£850 - £1849 / week

Enquire Enquire View

from £122 / night

1 / 11

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 9Min stay varies

  • 2 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £109 / night

£471 - £642 / week

Book Book View

from £109 / night

1 / 36

Villa Il Nido - Cortona villa sleeps 4

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
DescriptionIn one of the most beautiful scenery around Cortona, overlooking the Val di Chiana valley, you find Villa Il Nido.The Villa is isolated and immersed in a complete privacy and tranquility. All around the property you can admire a magnificent olive grove of 5 a  …see more

from £179 / night

£1250 - £2084 / week

Book Book View

from £179 / night

1 / 22

The Orangery: Cortona holiday villa with private pool and garden

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
“The Orangery” is a charming and cosy detached house wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely r  …see more

from £163 / night

£709 - £1246 / week

Book Book View

from £163 / night

(1) Excellent 

1 / 32

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £178 / night

£1246 - £2240 / week

Enquire Enquire View

from £178 / night

(10) Excellent 

1 / 24

Home-from-home comfort in the Tuscan hills

Tuscany / Province of Arezzo / Cortona / Ruffignano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
Get above and beyond the rat race in our cottage-style retreat! Here we offer self catering holidays in spacious, well presented accommodation that spans two levels of our secluded farm cottage, with its beautifully landscaped pool, located in tranquil hills 12 km (plu  …see more

from £109 / night

£730 - £1725 / week

Book Book View

from £109 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page