List your home
Apply filters
£ to

154 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 suburbs
  • Bagnolo (5)
  • Cegliolo (1)
  • Centoia (1)
  • Cignano (2)
  • Farinaio (1)
  • Fratta Sant'Agata (1)
  • Fratta Santa Caterina (1)
  • Fratticciola (7)
  • Mercatale di Cortona (15)
  • Montalla (1)
  • Montecchio, San Lorenzo (2)
  • Poggioni (2)
  • Ruffignano (2)
  • San Pietro a Cegliolo (5)
  • Terontola (3)

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
2,429 properties
Florence
937 properties
Trapani
490 properties
Venice, Veneto
473 properties
Amalfi Coast
454 properties
Cortona
426 properties
Lucca
426 properties
Palermo
375 properties
Sorrento, Campania
371 properties
Cefalu
310 properties
San Gimignano
293 properties
Greve in Chianti
263 properties
Massa Lubrense
259 properties
Taormina
257 properties

Filters applied: Private pool (154)

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
154 Results  |  
16 Photos

Villa | 6 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £941 /night

£6584 - £9920 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
A stunning completely renovated Tuscan farmhouse. The central stone building of the property dates back to the beginning of 1600, while the following sections were developed towards the end of 1800. It enjoys spectacular views across the Tuscan countryside  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £89 /night

£620 - £1081 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £110 /night

£769 - £1633 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

Featured properties

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
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Holiday house for 9 persons, with swimming pool , in Cortona  …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
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Apartment for 2 persons, with swimming pool , in Cortona  …see more

10 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £178 /night

£1240 - £2067 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £323 /night

£2257 - £3149 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Centoia with 6 bedrooms sleeps 12  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £154 /night

£1076 - £1649 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 4  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £169 /night

£1182 - £1962 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
Holiday house for 8 persons, with swimming pool , in Cortona  …see more

9 Photos

Farmhouse | 3 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £99 /night

£692 - £1145 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Montalla with 3 bedrooms sleeps 5  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 9

3 Nights min stay

Add to shortlist

from £125 /night

£875 - £1662 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Camucia with 5 bedrooms sleeps 9  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £237 /night

£1653 - £2364 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

16 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £136 /night

£951 - £2124 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

16 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £144 /night

£1005 - £1653 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £248 /night

£1731 - £3268 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 12  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £214 /night

£1496 - £2908 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 5 bedrooms sleeps 12  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £343 /night

£2397 - £3141 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £208 /night

£1451 - £2430 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This property is a grand villa set in Tuscany Italy. It has 6 bedrooms and 4 bathrooms, and it is perfect for those who are looking for a charming holiday. This property features: a swimming Pool, air Conditioning .  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £254 /night

£1773 - £3191 / week

View

Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Suitable 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 | 8 Bedrooms | sleeps 15

7 Nights min stay

Add to shortlist

from £172 /night

£1199 - £2505 / week

View

Key info:

  • Swimming pool
  • Suitable 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

16 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £95 /night

£662 - £910 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This small yet charming villa is situated in Cortona and it is ideal for small families.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £178 /night

£1240 - £2067 / week

View

Key info:

  • Swimming pool
  • Suitable 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

24 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £186 /night

£1302 - £2955 / week

View

Key info:

  • Nearest beach 170 km
  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Villa Corona is the best place for families and friends looking to spend their holidays relaxing in the stunning Val di Chiana.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £248 /night

£1732 - £3306 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
This villa for rent in Tuscany offers three double bedrooms, two twin bedrooms, private bathrooms for each, living rooms, dining rooms, a fully fitted kitchen and kitchenette and pool in the outside.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £254 /night

£1773 - £3306 / week

View

Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Suitable 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

19 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £136 /night

£946 - £2128 / week

View

Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Suitable 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

20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £182 /night

£1273 - £2720 / week

View

Key info:

  • Swimming pool
  • Suitable 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 | 5 Bedrooms | sleeps 9

3 Nights min stay

Add to shortlist

from £125 /night

£875 - £1662 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This property is a elegant villa set in Tuscany Italy. It has 5 bedrooms and 2 bathrooms, and it is ideal for those who are looking for a relaxing holiday. This property features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £375 /night

£2620 - £3463 / week

View

Key info:

  • Swimming pool
  • Suitable 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 8

7 Nights min stay

Add to shortlist

from £254 /night

£1773 - £3191 / week

View

Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £220 /night

£1538 - £2600 / week

View

Key info:

  • Nearest beach 170 km
  • Swimming pool
  • Suitable 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £130 /night

£909 - £1951 / week

View

Key info:

  • Swimming pool
  • Suitable 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 | 6 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £594 /night

£4153 - £5815 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 £189 /night

£1323 - £2067 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
This is a large villa for six people wanting to relax in a house with private pool and comfortable, ample indoor spaces. It features A/C and heating, kitchen, 4 bedrooms and parking space.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £125 /night

£875 - £1532 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

15 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £119 /night

£827 - £1633 / week

View

Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
This villa mixes the unique Tuscan style with elegant and modern comforts, and it is the perfect getaway for a family. It affords its own kitchen, 2 bedrooms and 2 bathrooms and a garden with swimming pool, BBQ area and spectacular views.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £154 /night

£1076 - £1649 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Set in Tuscany Italy, this charming villa is the perfect place for your holidays. The villa offers: a swimming Pool, an internet Connection .  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £1 /night

£1 - £3505 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
This house in Tuscany Italy with pool provides guests with accommodation for 12 guests in two different buildings with living-room, kitchen, and bedrooms with private bathrooms.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £638 /night

£4463 - £5455 / week

View

Key info:

  • Nearest beach 136 km
  • Swimming pool
  • Suitable 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 | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £214 /night

£1496 - £2908 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

20 Photos

Villa | 5 Bedrooms | sleeps 11

3 Nights min stay

Add to shortlist

from £142 /night

£992 - £1984 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable 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 £266 /night

£1860 - £2976 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Farmhouse | 5 Bedrooms | sleeps 11

4 Nights min stay

Add to shortlist

from £178 /night

£1240 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for over 5s only
  • 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

13 Photos

Villa | 5 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £136 /night

£947 - £2244 / week

View

Key info:

  • Swimming pool
  • Suitable 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

24 Photos

B&B | 4 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £107 /night

£744 / 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

13 Photos

Finca | 11 Bedrooms | sleeps 24

7 Nights min stay

Add to shortlist

from £473 /night

£3306 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • 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

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £296 /night

£2067 - £2480 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • 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

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

Min stay varies

Add to shortlist

from £130 /night

£910 - £1488 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Nestled in the foothills of Cortona, overlooking the Val di Chiana and Mount Amiata. The perfect base for exploring the beautiful regions of Tuscany and Umbria or simply relaxing, surrounded by nature.  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 16

Min stay varies

Add to shortlist

from £586 /night

£4100 - £6943 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Restored to high standard. Accommodation split in two private buildings. Ideal location between South Tuscany and Umbria. Private tennis court.  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 12

Min stay varies

Add to shortlist

from £354 /night

£2475 - £3765 / week

View

Key info:

  • Swimming pool
  • Suitable 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