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

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Cortona

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555 Holiday homes

Filters applied: Swimming pool

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

41

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Liliana is perfectly situated to enjoy the spectacular views of our beautiful valley. Villa Liliana sleeps up to 10 people.  …see more

from £295 / night

£2060 - £3513 / week

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from £295 / night

(1) Excellent 

13

Province of Arezzo / Cortona

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £85 / night

£594 / week

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from £85 / night

36

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Family friendly villa Luxury villas  …see more

from £327 / night

£2289 / week

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from £327 / night

(11) Excellent 

20

Apartment rental in Ruffignano with swimming pool

Cortona / Ruffignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“An Unforgettable Vacation” We stayed at the Tuscan Idyll in Cortona from mid-May to mid-June of 2014. Kate and Andrew’s home is truly an escape to days gone by. The home is located in the center of Cortona only steps away from all the action. It is be  …see more

from £111 / night

£742 - £1474 / week

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from £111 / night

16

Cortona holiday farmhouse rental

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 6  …see more

from £66 / night

£382 - £668 / week

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from £66 / night

14

Holiday apartment in Mercatale di Cortona

Cortona / Mercatale di Cortona

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
Apartment for a couple or a family with one or two children in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area. The kitchen is fully equipped and big and lighting bedroom have en-suite bathroom.  …see more

Pricing unknown

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Pricing unknown

25

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Walking distance to the town Family friendly villa  …see more

from £347 / night

£2424 - £3458 / week

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from £347 / night

(1) Very Good 

22

Holiday villa rental

Cortona / Montecchio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 155 km
  • Swimming pool
  • Child friendly
Villino Laura is an old mill immersed in the picturesque green Tuscan countryside only few kilometres from Cortona and has been completely restored maintaining its original charm. The furnishing of this property makes it one of a kind for its class, due to its precious  …see more

from £133 / night

£772 - £1102 / week

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from £133 / night

18

Province of Arezzo / Cortona

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £509 / night

£3390 / week

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from £509 / night

(6) Very Good 

51

Apartment accommodation in Montalla with shared pool

Cortona / Montalla

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
Azienda Fontelunga has some of the most appealing villas of the Cortona area available for rental.  …see more

from £130 / night

£700 - £1167 / week

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from £130 / night

19

Holiday apartment in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can also arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkWeddings  …see more

from £52 / night

£361 - £466 / week

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from £52 / night

15

Holiday cottage with swimming pool in Montecchio, San Lorenzo

Cortona / Montecchio, San Lorenzo

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
Character detached chestnut beamed cottage just below Cortona with terracotta tiles to sleep two with shared pool.  …see more

Pricing unknown

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Pricing unknown

(3) Excellent 

34

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £318 / night

£2221 - £3306 / week

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from £318 / night

(1) Excellent 

6

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

21

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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  …see more

from £110 / night

£763 - £1695 / week

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from £110 / night

19

Mercatale di Cortona holiday farmhouse rental

Cortona / Mercatale di Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
This apartment is on two floors: at the first there are the sitting room with fireplace, one double bedroom with bathroom, the kitchen, other bathroom and a terrace and at the second level the other double bedroom. There is independed heating and in the kitchen there is  …see more

from £128 / night

£721 / week

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from £128 / night

(1) Average 

37

Cortona holiday apartment rental

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Set in the verdant hills of the Valdichiana on the border between the Provinces of Arezzo and Siena the Fattoria delle Chianacce is a typical farmhouse built in the last century. These farms produced some of the very best beef and pork in the area and many continue to d  …see more

from £77 / night

£534 - £848 / week

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from £77 / night

23

Cortona / Fratta Santa Caterina

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £170 / night

£1272 / week

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from £170 / night

101

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
These apartments offer luxury and comfort in a very tranquil and refined atmosphere. They share a fantastic garden and swimming pool, and they’re located in a very strategic location.  …see more

Pricing unknown

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Pricing unknown

100

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Reggia Etruria is a wonderful complex of 4 apartments in Tuscany, all fitted with modern amenities and extremely comfortable, surrounded by a splendid panoramic garden with swimming, pool, and located nearby Arezzo, Pienza, Siena, and Cortona.  …see more

Pricing unknown

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Pricing unknown

46

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This wonderful stone house lying at the foot to an age old wood is surrounded by wild woods and olive trees. Nestled in the large well-kept garden full of plants a flowers, you will find the beautiful pool. The owners' love and care have turned the former farm hous  …see more

from £339 / night

£2373 - £3051 / week

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from £339 / night

29

Cortona holiday villa rental

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Le Contesse is a beautiful independent villa lying on a hillside, a few minutes from the Etruscan town of Cortona. A large park with holm-oaks and secular trees surrounds the villa, which commands a stunning view over the Valdichiana. Le Contesse has been furnishe  …see more

from £545 / night

£3814 / week

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from £545 / night

79

Cortona / Centoia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 16 km
  • Swimming pool

 …see more

from £102 / night

£678 - £1009 / week

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from £102 / night

7

Holiday apartment rental

Province of Arezzo / Cortona

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Apartment Sant' Angelo in Cortona is a bright and spacious one bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in typical Tuscan style, full of character, offering guests a warm vacation home.  …see more

from £85 / night

£594 / week

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from £85 / night

16

Holiday apartment with swimming pool in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
Flat for 4 people with outdoor patio in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area.The flat is perfect for 4 adults or for a family with 2 children. The kitchen is fully equipped and both bedrooms have en-suite bathroom.<  …see more

Pricing unknown

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Pricing unknown

15

Province of Arezzo / Cortona

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £162 / night

£1128 / week

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from £162 / night

5

Cortona / Mercatale di Cortona

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £30 / night

£509 / week

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from £30 / night

100

Apartment rental in Cortona with shared pool

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
These apartments offer luxury and comfort in a very tranquil and refined atmosphere. They share a fantastic garden and swimming pool, and they’re located in a very strategic location.  …see more

Pricing unknown

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Pricing unknown

(1) Very Good 

30

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 13 km
  • Swimming pool
  • Child friendly

 …see more

from £60 / night

£348 - £484 / week

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from £60 / night

(1) Excellent 

39

Cortona / Farinaio

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £243 / night

£1695 - £2543 / week

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from £243 / night

(3) Excellent 

30

Holiday cottage in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“PEACEFUL” Everything you could want from a holiday home in Tuscany. Very clean accommodation. Plenty of kitchen accessories. Air conditioning. Clean pool. Great food prepared by the owner upon request. Pizzas from heaven!  …see more

Pricing unknown

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Pricing unknown

16

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
A special hide-away in Tuscany ! Casa Serena is a really charming little house/villa is set in the middle of olive grove and surrounded Tuscan woodland, and provides privacy and serenity for a truly relaxing vacation. During Autumn and winter, there are the spec  …see more

from £99 / night

£691 - £1123 / week

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from £99 / night

101

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 17 km
  • Swimming pool

 …see more

from £509 / night

£3560 - £5594 / week

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from £509 / night

22

Holiday villa rental

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • 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 comp  …see more

from £166 / night

£721 - £1267 / week

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from £166 / night

15

Montalla holiday home let

Cortona / Montalla

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Independent stone house close to Cortona, a former middle age tower with terracotta floors and gothic windows. 8 sleeps, swimming pool  …see more

from £231 / night

£1611 / week

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from £231 / night

(11) Very Good 

28

Province of Arezzo / Cortona

11 24 Min stay varies

  • 11 bedrooms
  • Sleeps 24
  • Min stay varies
  • Nearest beach 8 km
  • Swimming pool
  • Child friendly

 …see more

from £43 / night

£297 - £5119 / week

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from £43 / night

100

Cortona holiday villa rental

Province of Arezzo / Cortona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly
Villa Corona is the best place for families and friends looking to spend their holidays relaxing in the stunning Val di Chiana.  …see more

from £260 / night

£1818 - £2712 / week

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from £260 / night

(2) Very Good 

12

Province of Arezzo / Cortona

6 6 Min stay varies

  • 6 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

25

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
At the foot of Cortona in a beautiful residential complex, antique oil mill, skilfully restored Sant'Angelo is a complete reconstructed Apartment respecting the characteristics of the epoch maintaining the original structure equipping it with every comfort of moder  …see more

from £94 / night

£424 - £721 / week

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from £94 / night

(4) Excellent 

20

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

6 16 7 nights min

  • 6 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

from £727 / night

£5085 - £6780 / week

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from £727 / night