List your home
Apply filters
£ to

338 Holiday homes in Cortona

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Arezzo Province Clear
  • Cortona Clear
  • All locations
  • Bagnolo (5)
  • Capezzine (1)
  • Cegliolo (3)
  • Centoia (6)
  • Cignano (31)
  • Farinaio (1)
  • Fratta Sant'Agata (1)
  • Fratta Santa Caterina (9)
  • Fratticciola (21)
  • Localita Mucchia (4)
  • Mercatale di Cortona (19)
  • Montalla (5)
  • Montanare (2)
  • Montecchio, San Lorenzo (4)
  • Poggioni (4)
  • Ruffignano (2)
  • San Pietro a Cegliolo (38)

more +

less -

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,500 properties
Florence
980 properties
Venice, Veneto
488 properties
Trapani
476 properties
Amalfi Coast
453 properties
Lucca
438 properties
Palermo
412 properties
Cortona
411 properties
Sorrento, Campania
351 properties
Cefalu
315 properties
San Gimignano
288 properties
Taormina
275 properties
Greve in Chianti
262 properties
Massa Lubrense
245 properties

Filters applied: Swimming pool (338)

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
338 Results  |  
9 Photos

Villa | 6 Bedrooms | sleeps 15

7 Nights min stay

Add to shortlist

from £420 /night

£2936 - £4421 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This incredible structure offers to its guests two different accommodations completely independent : the Villa and the cottage.  …see more

14 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £160 /night

£1120 - £1600 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Pets welcome
  • Private garden

Tucked away in the blissful rolling countryside on the edge of Cortona, this stone cottage with its private pool is a delightful hideaway for a couple seeking to experience the best of Tuscany and Umbria.

 …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £248 /night

£1730 - £2771 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 8  …see more

Featured properties

16 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £100 /night

£694 - £928 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £80 /night

£557 - £871 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 4  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

Add to shortlist

from £108 /night

£750 - £1734 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
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

8 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £87 /night

£605 - £904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Fratticciola with 2 bedrooms sleeps 4  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £58 /night

£406 - £603 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 3 persons, with swimming pool , in Cortona  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £54 /night

£377 - £564 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £70 /night

£484 - £888 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 4  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £231 /night

£1613 - £2307 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Amidst the olive trees that surround the walls of the ancient city of Cortona, lies Villa Olea, a delightful recently restored property, ideal for all who search privacy and tranquility.  …see more

12 Photos

Farmhouse | 7 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £271 /night

£1896 - £2533 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 7 bedrooms sleeps 16  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 14

4 Nights min stay

Add to shortlist

from £165 /night

£1154 - £2017 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
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

11 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £87 /night

£605 - £904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Fratticciola with 2 bedrooms sleeps 4  …see more

10 Photos

Farmhouse | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £52 /night

£363 - £636 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 6  …see more

20 Photos

House | 3 Bedrooms | sleeps 9

1 night min stay

Add to shortlist

from £118 /night

£820 - £1230 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Fastia Grande is a splendid apartment that covers the entire top floor of a villa. It sleeps nine people. From Villa Fastia Grande you will enjoy a pleasant view of the Tuscan hills and of the greenery  …see more

19 Photos

Villa | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £93 /night

£649 - £1089 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 4 persons, with swimming pool , in Cortona  …see more

10 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £87 /night

£605 - £904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Fratticciola with 2 bedrooms sleeps 4  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £58 /night

£406 - £603 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 2 persons, with swimming pool , in Cortona  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £289 /night

£2017 - £3025 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
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

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £51 /night

£351 - £726 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Livio A is a graceful apartment surrounded by the vegetation. It sleeps six people. It is appoximately 80 square meters (860 square feet). It features a shared swimming pool, a private terrace, a shared garden and winter heating. You will be roughly 3.5 km (2  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £74 /night

£516 - £767 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £139 /night

£968 - £1210 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £61 /night

£423 - £626 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Cortona  …see more

12 Photos

Farmhouse | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £340 /night

£2380 - £2742 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 9 bedrooms sleeps 18  …see more

8 Photos

Farmhouse | 3 Bedrooms | sleeps 7

3 Nights min stay

Add to shortlist

from £64 /night

£444 - £686 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 7  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £61 /night

£424 - £904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Fratticciola with 1 bedrooms sleeps 4  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £52 /night

£359 - £608 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
Apartment for 4 persons, with swimming pool , in Cortona  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £134 /night

£933 - £1681 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Holiday house for 9 persons, with swimming pool , in Cortona  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £133 /night

£928 - £2073 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
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

9 Photos

Farmhouse | 3 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £97 /night

£675 - £886 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Montalla with 3 bedrooms sleeps 5  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £58 /night

£400 - £605 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £49 /night

£337 - £566 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

15 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £231 /night

£1612 - £1761 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
Holiday house for 6 persons, with swimming pool , in Cortona  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £65 /night

£455 - £874 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 8  …see more

8 Photos

Farmhouse | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £57 /night

£394 - £585 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £203 /night

£1416 - £2371 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 6 bedrooms sleeps 12  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £181 /night

£1265 - £2530 / week

View

Key info:

  • Nearest beach 190 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Attractive holiday house for 10 persons, with swimming pool , in Arezzo  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £60 /night

£416 - £625 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 6  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £58 /night

£406 - £603 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 3 persons, with swimming pool , in Cortona  …see more

20 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £73 /night

£509 - £863 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 2  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £47 /night

£325 - £539 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
Apartment for 2 persons, with swimming pool , in Cortona  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £58 /night

£400 - £767 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Casa Livio D is a graceful two-story apartment surrounded by meadows and by green hills. It sleeps six people. It is appoximately 90 square meters (970 square feet). It features a shared swimming pool, a shared garden, a reserved outdoor area and winter heating  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £53 /night

£371 - £627 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £223 /night

£1559 - £3031 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Holiday house for 12 persons, with swimming pool , in Cortona  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £77 /night

£534 - £643 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
  • Private garden
Apartment for 2 persons, with swimming pool , in Cortona  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £118 /night

£823 - £1372 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 10  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £108 /night

£750 - £1593 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
La Farnetina is a charming independent Villa, part of a big property dating back to the first years of the 20th century, located in a beautiful position in the countryside around Cortona, at only 14 Km from the historical centre.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

Add to shortlist

from £133 /night

£928 - £2017 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Villa Berta is a spacious three-story villa surrounded by the vegetation. It sleeps 12 people. From Villa Berta you will have a pleasant view of the Tuscan countryside. Villa Berta is 170 square meters (1830 square feet)  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £56 /night

£388 - £684 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Holiday house for 6 persons in Cortona  …see more