Villas with a pool Cortona | Apartments to rent with swimming facilities

Close

View larger map

Price per night

to

Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
  • All locations
  • Bagnolo (3)
  • Capezzine (2)
  • Cegliolo (5)
  • Centoia (7)
  • Farinaio (3)
  • Fratta Santa Caterina (9)
  • Fratticciola (10)
  • Localita Mucchia (2)
  • Mercatale (4)
  • Mercatale di Cortona (16)
  • Montalla (18)
  • Montanare (7)
  • Montecchio (14)
  • Montecchio, San Lorenzo (2)
  • Pietraia (8)
  • Poggioni (4)
  • Ruffignano (1)
  • Teverina (8)

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
Montalla
21 properties
Montecchio
18 properties
Mercatale di Cortona
17 properties
Fratticciola
11 properties
Fratta Santa Caterina
10 properties
Montanare
10 properties
Teverina
10 properties
Pietraia
9 properties
Centoia
8 properties
Mercatale
7 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

517 Holiday homes

Filters applied: Swimming pool (517)

1 / 53

Villa San Pietro - Cegliolo villa sleeps 10

Cortona / Cegliolo

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
This stunning villa is located 5 km from Cortona. Recently renovated and nicely furnished, it is an 18th century Tuscan stone house. Surrounded by olive trees and facing south with lovely views across the valley below, Villa San Pietro is very private and quiet with tra  …see more

from £299 / night

£2087 - £3566 / week

Book Book View

from £299 / night

1 / 22

Cortona / Bagnolo

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £261 / night

£1000 - £2653 / week

Book Book View

from £261 / night

1 / 33

La Certosa - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Description: A spacious farmhouse located in a spectacular, private and tranquil hillside setting that includes 15 acres of terraced olive groves and fruit trees (pears, plums, cherry and apple.) Cortona, with its shops, restaurants and open air market is a 20-minute wa  …see more

from £497 / night

£3479 - £4392 / week

Book Book View

from £497 / night

(1) Excellent 

1 / 25

Fonte al Vento:the Villa - Cortona villa sleeps 10

Province of Arezzo / Cortona

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Fonte al Vento is a detached villa 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 respect the privacy of  …see more

from £434 / night

£2522 - £3696 / week

Book Book View

from £434 / night

1 / 24

Fattoria Borgonuovo - Rosa - Cortona lodge sleeps 4

Province of Arezzo / Cortona

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
The "Fattoria Borgonuovo" is located in an agricultural and hilly area of the Val di Chiana, very close to the beautiful and old town of Cortona, and a short distance from the most important historical and wine centers of the southern part of Tuscany, as, Mont  …see more

from £57 / night

£392 - £479 / week

Book Book View

from £57 / night

(1) Excellent 

1 / 13

LE MURA ETRUSCHE - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
THE CHARM OF THE MIDDLE AGES-Etruscan walls, a wonderful and relaxing view over the Chiana Valley from the beautiful terrace, above the Etruscan walls.A building of 1200 decorated with love between ancient and modern, a garden that is based on the Etruscan walls, after  …see more

from £57 / night

£392 - £566 / week

Book Book View

from £57 / night

(10) Excellent 

1 / 24

Home-from-home comfort in the Tuscan hills

Cortona / Ruffignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
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 £114 / night

£761 - £1800 / week

Book Book View

from £114 / night

(1) Excellent 

1 / 24

Villa Primula - Cortona villa sleeps 9

Province of Arezzo / Cortona

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 30 km; Swimming pool;
Dating back to the 19th century, the welcoming Villa Primula is the perfect choice for all those who want to live the real charme of Tuscany without the need of relying constantly on a car while on holiday. Sleeping up to 9 guests in 5 bedrooms and benefitting from a be  …see more

from £85 / night

£514 - £1470 / week

Book Book View

from £85 / night

1 / 101

Province of Arezzo / Cortona

10 20 7 nights min stay

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 17 km; Swimming pool;
 …see more

from £491 / night

£3435 - £4348 / week

Book Book View

from £491 / night

(1) Very Good 

1 / 24

Il Cipresso apt in farmhouse with swimming pool

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
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 £114 / night

£740 - £1131 / week

Book Book View

from £114 / night

(34) Excellent 

1 / 25

Il Villino di Cortona (Property at exclusive use)

Province of Arezzo / Cortona

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 150 km; Swimming pool; Child friendly ;
"Il Villino di Cortona", cosy holiday home nestled in the green heart of the Chiana Valley in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in contact with nature ... "Il Villino di Cortona”, is a small holiday home, nestled in the Va  …see more

from £83 / night

£531 - £748 / week

Book Book View

from £83 / night

1 / 11

Province of Arezzo / Cortona

2 9 Min stay varies

  • 2 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £114 / night

£492 - £670 / week

Book Book View

from £114 / night

(2) Very Good 

1 / 24

Fattoria Borgonuovo - Geranio - Cortona lodge sleeps 4

Province of Arezzo / Cortona

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
The "Fattoria Borgonuovo" is located in an agricultural and hilly area of the Val di Chiana, very close to the beautiful and old town of Cortona, and a short distance from the most important historical and wine centers of the southern part of Tuscany, as, Mont  …see more

from £57 / night

£392 - £479 / week

Book Book View

from £57 / night

1 / 19

Agriturismo Poggio del Fabbro - Poggioni villa sleeps 7

Cortona / Poggioni

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Child friendly ; 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 £112 / night

£780 / week

Book Book View

from £112 / night

1 / 21

Villa Neri - Cortona villa sleeps 12

Province of Arezzo / Cortona

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Villa Neri is situated in San Lorenzo in close driving proximity to Cortona. Cortona is an antique Etruscan town which lies in the heart of the Chiana valley. You can even see the town perched on the hill in front of you. The position is isolated and it will offer you c  …see more

from £113 / night

£783 - £1740 / week

Book Book View

from £113 / night

(1) Excellent 

1 / 44

Il Ciliegio - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Wonderful and elegant villa situated in a quiet position on the green hills which surround Cortona.The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.The house is tastefully furnished and is equipped with a  …see more

from £152 / night

£1058 - £1740 / week

Book Book View

from £152 / night

1 / 34

Cortona / Montanare

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £61 / night

£392 - £522 / week

Book Book View

from £61 / night

1 / 30

Province of Arezzo / Cortona

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 13 km; Swimming pool; Child friendly ;
 …see more

from £64 / night

£374 - £392 / week

Book Book View

from £64 / night

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 - £1595 / week

Book Book View

from £157 / night

1 / 100

Panorama - Cortona villa sleeps 8

Province of Arezzo / Cortona

5 8 7 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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 Chian  …see more

from £394 / night

£2757 - £3270 / week

Enquire Enquire View

from £394 / night

1 / 36

Villa Il Nido - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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 £187 / night

£1305 - £2174 / week

Book Book View

from £187 / night

(1) Excellent 

1 / 28

Giusi e Dario - Montanare villa sleeps 12

Cortona / Montanare

5 12 7 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
main HouseA charming Tuscan villa designed, decorated and furnished by 'Giusi', the Italian cook who often helps friend Frances Mayes prepare splendid luncheons and dinner parties at Villa Bramasole, near Cortona. Giusi is mentioned and photographed in Frances  …see more

from £342 / night

£2392 - £5609 / week

Book Book View

from £342 / night

1 / 31

Luxury villa in Cortona - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
This magnificent villa is located at 400 m from the lovely 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. This elegant vill  …see more

from £410 / night

£2870 - £4522 / week

Book Book View

from £410 / night

(3) Excellent 

1 / 20

Casale Ruffignano - Cortona villa sleeps 16

Province of Arezzo / Cortona

6 16 7 nights min stay

  • 6 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.Villa Ruffigano dates back to the 16th century and was the centre of an antique farm on which 30 people worked.Guests ca  …see more

from £584 / night

£4087 - £6000 / week

Book Book View

from £584 / night

(1) Very Good 

1 / 31

IL CASALE DI CARMINA - Mercatale di Cortona villa sleeps 10

Cortona / Mercatale di Cortona

5 10 4 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Located 800 meteres above sea level, overlooking the Val di Pierle, which is the most eastern area of the town of Cortona, in the tranquillity of the verdant Hills of Tuscany, IL CASALE DI CARMINA is an old mansion completely restored and furnished in a rustic style wit  …see more

from £174 / night

£1044 - £1305 / week

Book Book View

from £174 / night

1 / 100

Lucente - Cortona villa sleeps 8

Province of Arezzo / Cortona

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 136 km; Swimming pool; Child friendly ;
Exterior This idyllic villa is located in the east of Tuscany, in the heart of the Val di Chiana, near the enchanting town of Cortona. From the villa, you’ll enjoy breathtaking panoramic views of the Val di Chiana. The villa is surrounded by olive trees  …see more

from £671 / night

£4696 / week

Enquire Enquire View

from £671 / night

1 / 41

Villa Liliana - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Villa Liliana is perfectly situated to enjoy the spectacular views of our beautiful valley. Villa Liliana sleeps up to 10 people.On the ground floor, a spacious hallway entry foyer leads into a living room and one bedroom with en-suite bathroom. The spacious kitchen, on  …see more

from £302 / night

£2114 - £3605 / week

Book Book View

from £302 / 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 £151 / night

£1057 - £1431 / week

Book Book View

from £151 / night

1 / 42

Province of Arezzo / Cortona

3 6 Min stay varies

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

from £69 / night

£479 - £870 / week

Book Book View

from £69 / night

1 / 25

Casale della Torre - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Villa Casale Mulino is a property situated on about 10 acres of terraced land which has olive tree groves and vineyards. It's a perfect starting point for panoramic walks or biking. The spectacular panorama that this villa offers will be the missing ingredient for  …see more

from £356 / night

£2487 - £3548 / week

Book Book View

from £356 / night

1 / 35

Casa Fontelunga, ancient tuscan villa with pool

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car not necessary;
Casa Fontelunga is a lovely country house placed in an enchanted location hillside, between our olive plantation and just a few minutes from the beautiful art city of Cortona, made famous worldwide from the book and movie 'Under the Tuscan Sun'.Privacy and qui  …see more

from £201 / night

£1174 - £1957 / week

Book Book View

from £201 / night

(1) Very Good 

1 / 36

VILLA FRANCESCA Cortona - 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 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 £141 / night

£983 - £1670 / week

Book Book View

from £141 / night

1 / 24

Province of Arezzo / Cortona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
 …see more

from £109 / night

£740 - £783 / week

Book Book View

from £109 / night

1 / 36

Villa Orlando - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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.You will enjoy a spacious , fully equipped kitche  …see more

from £286 / night

£2000 - £3605 / week

Book Book View

from £286 / night

1 / 23

Biancospino - Poggioni villa sleeps 12

Cortona / Poggioni

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
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.These places evoke a charm with flavors of ancient times and represent the secret soul of the most profound Tuscan  …see more

from £116 / night

£809 - £2174 / week

Book Book View

from £116 / night

1 / 16

Le Casine - Girasole Apartment - Fratta Santa Caterina apartment sleeps 4

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £59 / night

£409 - £552 / week

Book Book View

from £59 / night

1 / 20

Cortona - 41349002 - Cortona farmhouse sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
Nice complex comprising 2 small independent stone villas which have been recently restored. This property is situated in panoramic location on the hills surrounding the beautiful medieval town of Cortona which is only 10 km away. Both villas offer comfortable interiors  …see more

from £62 / night

£434 - £922 / week

Enquire Enquire View

from £62 / night

1 / 34

Villa le Contesse - Cortona villa sleeps 14

Province of Arezzo / Cortona

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Villa Mariani is situated on the hillside leading up the eastern flank of Cortona, while the town is just 5 minutes away by car or 20 minutes on foot. A large park with holm-oaks and pine trees surrounds the villa, which commands a stunning view over the Valdichiana. T  …see more

from £560 / night

£3914 - £5590 / week

Book Book View

from £560 / night

(1) Good 

1 / 24

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car not necessary;
 …see more

from £57 / night

£627 - £792 / week

Book Book View

from £57 / night

(8) Excellent 

1 / 30

Fantastic 5 bedroom Tuscan farmhouse with panoramic views and swimming pool

Province of Arezzo / Cortona

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
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 £348 / night

£2609 - £3479 / week

Book Book View

from £348 / 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