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

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona

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  • Bagnolo (3)
  • Capezzine (2)
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  • Mercatale di Cortona (16)
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  • Teverina (6)

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479 Holiday homes

Filters applied: Swimming pool (479)

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

(1) Excellent 

1 / 28

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 £181 / night

£1261 - £2233 / week

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from £181 / night

1 / 27

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 £135 / night

£718 - £1196 / week

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from £135 / night

1 / 19

Province of Arezzo / Cortona

15 bedroomsSleeps 30Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £774 / night

£5463 - £8404 / week

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from £774 / night

Featured properties

(4) Excellent 

1 / 4

Family Tuscan Villa Private Pool, Lovely Views

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 ; Some pets are welcome - please contact the owner;
For those who enjoy privacy, this beautifully restored traditional Tuscan farm house and Private Pool, offers the opportunity experience real Tuscan living. The house has 3- 4 bedrooms ( 2 double bedrooms, 1 twin bedroom and an option of a further bed in the study), t  …see more

from £211 / night

£1471 - £2093 / week

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from £211 / night

1 / 20

Province of Arezzo / Cortona

9 bedroomsSleeps 18Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Some pets are welcome - please contact the owner;
 …see more

from £253 / night

£1765 - £3572 / week

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from £253 / night

1 / 19

Castiglion Fiorentino - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Car essential;
This generous and luxurious apartment is settled on the ground floor and each bedroom has it's own outside space. The different levels of a few steps gives it a charming feeling of a house without the weight of it. It is comfortable and tastefully furnished with all mod  …see more

from £148 / night

£837 - £1135 / week

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from £148 / night

(2) Excellent 

1 / 34

Luxury Villa in Cortona 8 - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £343 / night

£2395 - £3530 / week

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from £343 / night

1 / 21

Peschino - Teverina villa sleeps 12

Cortona / Teverina

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Casa Peschino sits on the lower slopes of a quiet side valley, with stunning and extensive views over the green countryside of woods, vineyards, olive groves and farmland. It is reached by a short track through fields of sunflowers, wild flowers, maize and tobacco plant  …see more

from £246 / night

£1720 - £2710 / week

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from £246 / night

1 / 17

Province of Arezzo / Cortona

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £186 / night

£1085 - £1891 / week

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from £186 / night

(1) Excellent 

1 / 31

ANTICO PALLAIO - Cortona villa sleeps 9

Province of Arezzo / Cortona

3 bedroomsSleeps 93 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. beatiful wiew over the chiana valley. all the old charme of tuscany. 4bedroom, 4 bathroomLocated in the village of Ossaia ( 3 km from Cortona), the property  …see more

from £253 / night

£1681 / week

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from £253 / night

(1) Excellent 

1 / 14

Province of Arezzo / Cortona

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £55 / night

£240 - £370 / week

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from £55 / night

1 / 24

Province of Arezzo / Cortona

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £202 / night

£1261 - £1681 / week

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from £202 / night

(7) Very Good 

1 / 33

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 £679 / night

£4750 - £6182 / week

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from £679 / night

1 / 24

Fattoria Borgonuovo - Rosa - Cortona lodge sleeps 4

Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
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 £55 / night

£379 - £580 / week

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from £55 / night

1 / 30

Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 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 £275 / night

£1924 - £2993 / week

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from £275 / night

1 / 36

Villa Orlando - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £277 / night

£1933 - £3484 / week

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from £277 / night

1 / 31

Luxury villa in Cortona - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £397 / night

£2774 - £4370 / week

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from £397 / night

1 / 31

Villa Nello - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Above the wood oven is engraved 1781. Villa Nello was restored in 2001. It develops on three floors, sleeping 8 people, plus a small independent single bedroom with bathroom. The ground floor includes an entrance foyer, adjoining dining room and kitchen leading to a lar  …see more

from £601 / night

£4202 / week

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from £601 / night

(1) Excellent 

1 / 12

Large Tuscan farmhouse apartment in beautiful Cortona countryside, four bedrooms, pool access

Province of Arezzo / Cortona

4 bedroomsSleeps 6Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
The apartment is independent, and has beautiful piece of ancient furniture own heating system, some of them has a fire-place. This has a own outside space and very well fitted out with garden furniture, all equipped with every thing necessary to be efficient and functi  …see more

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(4) Excellent 

1 / 17

Province of Arezzo / Cortona

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £269 / night

£1849 - £3278 / week

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from £269 / night

1 / 24

Province of Arezzo / Cortona

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
 …see more

from £106 / night

£715 - £757 / week

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from £106 / night

(2) Very Good 

1 / 12

Cortona villa in beautiful Tuscan countryside

Province of Arezzo / Cortona

3 bedroomsSleeps 57 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
The sitting room has an old open fireplace and impressive, ancient wooden beams. Two comfy sofas are a nice modern addition! The dining room is authentic Italian 1950s decor under more seriously ancient ceiling beams. The atmosphere at San Silvestro is one of homely cou  …see more

from £93 / night

£650 - £1090 / week

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from £93 / night

(1) Excellent 

1 / 25

Fonte al Vento:the Villa - Cortona villa sleeps 10

Province of Arezzo / Cortona

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £420 / night

£2437 - £3572 / week

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from £420 / night

1 / 34

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 £241 / night

£1681 - £3606 / week

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from £241 / night

1 / 34

Cortona / Montanare

1 bedroomSleeps 3Min stay varies

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

from £59 / night

£379 - £505 / week

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from £59 / night

1 / 37

Province of Arezzo / Cortona

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 145 km; Swimming pool; Great for children of all ages ;
 …see more

from £80 / night

£513 - £723 / week

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from £80 / night

1 / 100

Il Furioso - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 160 km; Swimming pool; Great for children of all ages ;
ExteriorsThis villa with pool near Cortona can accommodate up to 8 people and it is perfect for families or groups that like to spend their time enjoying the outdoors.It features a lovely outdoor terrace with a table seating 12 people and a small cooking nook with  …see more

from £277 / night

£1933 - £3110 / week

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from £277 / night

(2) Excellent 

1 / 20

Ca de Muito, a peaceful Tuscan cottage with breathtaking views and a private outdoor pool

Cortona / Mercatale di Cortona

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 20 km; Swimming pool; Great for children of all ages ;
Charming Ca de Muito has an idyllic position on the Tuscany side of the Niccone Valley. The views of the stunning countryside are breath-taking, they stretch over the Niccone Valley including 2 picturesque castles, to the village of Preggio on the opposite hillside. W  …see more

from £146 / night

£1021 - £1433 / week

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from £146 / night

(10) Excellent 

1 / 24

Home-from-home comfort in the Tuscan hills

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 £110 / night

£736 - £1740 / week

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from £110 / night

(17) Excellent 

1 / 34

Province of Arezzo / Cortona

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 16 km; Swimming pool;
 …see more

from £181 / night

£1261 - £2522 / week

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from £181 / night

(1) Excellent 

1 / 37

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 £169 / night

£967 - £2564 / week

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from £169 / night

1 / 14

Le Casine - Bugia Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • 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 £51 / night

£352 - £466 / week

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from £51 / night

1 / 42

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 ; Air conditioning;
 …see more

from £67 / night

£463 - £841 / week

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from £67 / night

(1) Excellent 

1 / 28

Giusi e Dario - Montanare villa sleeps 12

Cortona / Montanare

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £331 / night

£2311 - £5421 / week

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from £331 / night

(8) Excellent 

1 / 35

Villa Nobile is a stunning 19th Century Villa

Province of Arezzo / Cortona

7 bedroomsSleeps 243 nights min stay

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min stay
Key info: Nearest beach 250 km; Swimming pool; Great for children of all ages ;
Villa Nobile is a stunning 19th Century classical style villa recently restored authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land. A private avenue of young cypresses bringing you to our doorstep. Tran  …see more

from £64 / night

£463 / week

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from £64 / night

1 / 41

Villa Liliana - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £292 / night

£2043 - £3484 / week

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from £292 / night

1 / 19

Le Casine - Mela Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • 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 £51 / night

£352 - £466 / week

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from £51 / night

1 / 22

The Orangery: Cortona holiday villa with private pool and garden

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 £164 / night

£715 - £1257 / week

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from £164 / night

1 / 20

Province of Arezzo / Cortona

4 bedroomsSleeps 12Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Car advised;
 …see more

from £169 / night

£1093 - £2404 / week

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from £169 / night

1 / 30

Province of Arezzo / Cortona

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 13 km; Swimming pool; Great for children of all ages ;
 …see more

from £40 / night

£237 - £420 / week

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from £40 / night

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