List your home
Apply filters
£ to

138 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)
  • Cegliolo (1)
  • Centoia (1)
  • Cignano (1)
  • Farinaio (1)
  • Fratta Sant'Agata (1)
  • Fratticciola (4)
  • Mercatale di Cortona (14)
  • Montanare (1)
  • Montecchio, San Lorenzo (2)
  • Poggioni (2)
  • Ruffignano (2)
  • San Pietro a Cegliolo (4)

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
2,403 properties
Florence
1,000 properties
Venice, Veneto
512 properties
Trapani
474 properties
Amalfi Coast
462 properties
Lucca
441 properties
Palermo
418 properties
Cortona
388 properties
Sorrento, Campania
388 properties
Cefalu
315 properties
Taormina
273 properties
San Gimignano
270 properties
Massa Lubrense
254 properties
Greve in Chianti
239 properties

Filters applied: Private pool (138)

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
138 Results  |  
15 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £259 /night

£1808 - £3408 / week

View

Key info:

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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £122 /night

£854 - £1495 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

Add to shortlist

from £132 /night

£924 - £1730 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
The property is situated on the hills which surround Cortona. It's a characteristic villa in rustic style which develops on two independent levels, each equipped with kitchen and comforts.  …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
  • 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 | 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
  • 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 8

7 Nights min stay

Add to shortlist

from £335 /night

£2339 - £3065 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Located in Cortona, this fabulous villa offers a fabulous swimming pool, a fully equipped kitchen and a special surprise in each room to help guests relax and enjoy the best of holidays.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £179 /night

£1250 - £2661 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This traditional villa in Cortona for 14 people is perfect for a large group of friends. The accommodation offers a swimming pool and a pet-friendly space.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 15

7 Nights min stay

Add to shortlist

from £169 /night

£1177 - £2452 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This secluded Cortona farmhouse for 15 people is perfect for families and friends. Situated in the Tuscan province of Arezzo, this villa boasts a magnificent swimming pool.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £412 /night

£2884 / week

View

Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This lovely villa near Cortona can accommodate up to 10 people. It has a swimming pool and 3 bedrooms with en-suite bathrooms.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £215 /night

£1500 - £2077 / week

View

Key info:

  • Nearest beach 170 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
A large and traditional villa for 8, with four bedrooms, a fully equipped kitchen, private garden with swimming pool, BBQ area and playground, and stunning views of the surroundings.  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £132 /night

£923 - £2077 / week

View

Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
The spacious bedrooms and common areas in this villa make it perfect for families or large groups of friends. It boasts its own garden with outdoor furniture and swimming pool, a full kitchen and all modern comforts.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £122 /night

£854 - £1495 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This property is a pleasant villa set in Tuscany Italy. It has 3 bedrooms and 2 bathrooms, and it is ideal for those who are looking for an unforgettable experiencie. This property features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly s...  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £209 /night

£1459 - £2838 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This property is a beautiful villa set in Tuscany Italy. It has 5 bedrooms and 4 bathrooms, and it is ideal for those who are looking for an unforgettable experiencie. This property features: a swimming Pool, air Conditioning .  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £127 /night

£887 - £1912 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This charming accommodation located in Tuscany, Italy, has a maximum capacity of 8 people. This property comes with a swimming pool and is ideal for families and friends.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £434 /night

£3033 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Villa 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. The main villa can host up to 6 guests, while two annexes increase the c  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £396 /night

£2771 / week

View

Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This cozy villa in Cortona can accommodate up to 6 people. It has a swimming pool, a living room, 5 bedrooms and 5 bathrooms.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £579 /night

£4053 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Set in Tuscany Italy, this charming accommodation is the perfect place for your holidays. The accommodation offers: a swimming Pool, air Conditioning, an internet Connection .  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £396 /night

£2771 / week

View

Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This villa with pool near Cortona in Tuscany can accommodate up to 8 people and features a kitchen, a dining room and two living rooms, 4 bedrooms and 4 bathrooms and breathtaking views over the Valdichiana.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 11

3 Nights min stay

Add to shortlist

from £139 /night

£968 - £1936 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Farmhouse near Cortona, in the Chiana Valley with wonderful panoramic view. Ideal solution for relaxing holidays in the Tuscan countryside. Swimming pool, barbecue, Internet connection, table-tennis table, mountain bikes. Tennis club and riding stable nearby.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

3 Nights min stay

Add to shortlist

from £275 /night

£1924 - £3078 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Ideal for families with children of all ages - Extreme silence and peace - Maximum privacy - Healthy enviromnment - Beautiful and spacious landscape - Maximum hygiene - Comfortable furnishings - Air Conditioning - COmplete with all the amenities - Heated pool and secure  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £62 /night

£428 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
agriturismo cortona teccognano beppe toscana cucina tipica Wi fi piscina  …see more

24 Photos

B&B | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

Add to shortlist

from £110 /night

£770 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Casa Bellavista è nel cuore della campagna in poco tempo si possono raggiungere importanti centri come Cortona, Arezzo, Pienza, Montepulciano, Siena, Montalcino, Chianti, Assisi. Simonetta è a vostra disposizione per suggerirvi i migliori percorsi per una toscana slow. I corsi di cucina vengono svolti nella cucina di Casa Bellavista, assaporando i veri sapori di cibi semplici  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 11

4 Nights min stay

Add to shortlist

from £184 /night

£1283 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children over
  • Car advised
  • Pets welcome
  • Private garden
A traditional stone house set in the restful landscape of the tuscan hills, provided with all comforts, very close to the main touristic destinations of central Italy. Art, culture, wine and food, Umbria jazz festival, the wonderful Trasimeno beaches, and much more...  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £159 /night

£1112 - £1625 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa indipendente in mezzo ad una secolare oliveta, ad 1 chilometro circa dalla città di Cortona, set del famoso film Under Tuscan Sun girato a circa 300 metri dalla nostra casa. 8 posti letto, ampio giardino attrezzato, piscina esclusiva, parcheggio all'interno. Possibilità di aria condizionata a richiesta  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £140 /night

£979 - £1834 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Vivete un'esperienza a contatto con la natura ma con tutti i confort della vita moderna.  …see more

15 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £80 /night

£556 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Agriturismo Cortona Teccognano S. Angelo Beppe Cucina tipica Toscana Wi-Fi piscina  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £306 /night

£2138 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
La posizione è ideale per chi desidera visitare, con brevi spostamenti, le due regioni dell'Italia centrale Toscana ed Umbria trovandosi Cortona sulla linea principale delle strade a scorrimento veloce come l'Autostrada A1 e la superstrada Siena-Perugia. tranquillità e pace sono le principali prerogative di una vacanza nella nostra casa  …see more

13 Photos

Finca | 11 Bedrooms | sleeps 24

Min stay varies

Add to shortlist

from £367 /night

£2565 - £3420 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Casale toscano con piscina. Ampi appartamenti di lusso con aria condizionata . Viene affittato in esclusiva . Vicino all'autostrada ma immerso nella pace e silenzio della campagna toscana .  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 16

Excellent 5/5 

Min stay varies

Add to shortlist

from £300 /night

£2100 - £2900 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

7 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £742 /night

£5194 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Private Villa in Cortona Area, Near Montepulciano, Tuscany, Italy. Private Swimming Pool, sleeps 18. Beautiful gardens, green grass all year. Multiple family accommodation. Broadband, TV, DVD, iPod docks, table-tennis, bikes.  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

from £153 /night

£1069 - £1283 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Family- friendly 3 bedroom restored Farmhouse with private pool, just below Cortona  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 12

Min stay varies

Add to shortlist

from £354 /night

£2475 - £2835 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Torre degli Elci is set in the greens of the Tuscan countryside, midst olives and cypress trees and just 4 km from Cortona. The name of the Villa derives from the old sighting tower which has testimonials from 13th and 14th century and which became a monastery  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

from £307 /night

£2145 - £3145 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Lovingly restored in 2004 Villa Orlando sleeps 8 people comfortably with four bedrooms, all with en-suite bathrooms with showers. This villa is perfect for families or groups that like to spend time enjoying the outdoors.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Min stay varies

Add to shortlist

from £287 /night

£2003 - £2940 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This charming old villa inserted in the enchanting setting of the typical chiana valley Tuscan landscape, Villa Salcotto lies at the foot of the hill of Cortona, a delightful town whose Etruscan origins left it with a still very conspicuous archaeological heritage  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

Good 3/5 

Min stay varies

Add to shortlist

from £132 /night

£924 - £1730 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Gloria is a quaint cottage that is set in a charming and panoramic position, with completely authentic surroundings. Immersed in the lush mountains of Cortona, near the border between Tuscany and Umbria  …see more

19 Photos

Villa | 9 Bedrooms | sleeps 18

Min stay varies

Add to shortlist

from £340 /night

£2380 - £3549 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
A holiday farm for a different holiday experience in untouched nature and relaxation. The Palazzo is an enchanting late 19th century country building recently fully renovated and restored, returning to its ancient splendour through accurate work, divided in 6 apartments  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

  • Nearest beach 136 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Villa Lucente is the perfect villa for those wanting an idyllic holiday in Tuscany. The villa is located in the heart of the Val di Chiana in Tuscany, near the enchanting town of Cortona, you'll enjoy breathtaking views of the surrounding countrysid  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This villa in Cortona's countryside sleeps up to 4 people. It is fully equipped and it even boasts its own garden and swimming pool. It is close to the famous art cities in the region so it works as an ideal starting point for a holiday in Tuscany.  …see more