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

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Cortona

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571 Holiday homes

Filters applied: Swimming pool (601)

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

8

Holiday apartment with swimming pool in Cortona

Province of Arezzo / Cortona

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Le Gelosie apartments” are the natural and inviting alternative to our hospitality and combine good taste and attention for details.  …see more

from £88 / night

£615 / week

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from £88 / night

16

Holiday apartment with shared pool in Fratticciola

Cortona / Fratticciola

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
In the surroundings of Cortona, one of the most wonderful cities of art in Tuscany, lies the Agriturismo Isolina, deep in the green hills of the valley Valdichiana.  …see more

from £151 / night

£1053 / week

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from £151 / night

23

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £62 / night

£395 - £527 / week

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from £62 / night

33

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Surrounded by the gentle hills which frame the medieval town of Cortona, Villa Eugenio will assure you a peaceful vacation in the heart of Tuscany. This beautiful 17th century Tuscan farmhouse has been painstakingly restored and turned into a warm and welcoming country  …see more

from £195 / night

£1360 - £2167 / week

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from £195 / night

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 £97 / night

£439 - £746 / week

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from £97 / night

(1) Excellent 

81

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 18 km
  • Swimming pool

 …see more

from £88 / night

£527 - £860 / week

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from £88 / night

29

Holiday apartment in Cortona

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • 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 £43 / night

£299 - £553 / week

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from £43 / night

100

Cortona holiday apartment rental

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
These apartments for rent in Tuscany housed in a farmhouse lie atop a hill with full view of the walls of Cortona.  …see more

from £79 / night

£544 - £790 / week

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from £79 / night

100

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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

27

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Surrounded by the gentle rolling hills surrounding the ancient city of Cortona, Eugenio Villa offers an unforgettable holiday of privacy and tranquility. Careful restoration has transformed this typical Tuscan farmhouse of the XVII century in a house warm and cozy count  …see more

from £195 / night

£1360 - £2794 / week

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from £195 / night

20

Holiday villa rental

Province of Arezzo / Cortona

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Beautiful farmhouse at the foot of Cortona,surrounded by 7000sqm of land cultivated with olive and fruit trees. Located in the village of Pergo, famous for its prestigious villas and farmhouses of which is scattered and of which it is part.  …see more

Pricing unknown

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Pricing unknown

100

Holiday apartment in Cignano

Cortona / Cignano

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
This agriturismo features a large outdoor pool and has seven apartments that can accommodate between 2 and 8 people.  …see more

from £71 / night

£400 - £615 / week

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from £71 / night

100

Holiday apartment in Cignano

Cortona / Cignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
This agriturismo features a large outdoor pool and has seven apartments that can accommodate between 2 and 8 people.  …see more

from £110 / night

£676 - £1167 / week

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from £110 / night

19

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
Casa Patrizia is a typical holiday house. The villa has a completely independent apartment on the ground floor with two entrances, with private garden, veranda with table and chairs, elegantly furnished and decorated in typical Tuscan style.  …see more

from £126 / night

£878 - £1316 / week

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from £126 / night

12

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
An elegant, 17th Century Tuscan Farmhouse in a glorious location among Tuscan and Umbrian hills, only minutes from the beautiful Etruscan walled town of Cortona. Perfect all year round: walk or cycle in the hills, soak at the Thermal Spa, shop in fresh produce markets,  …see more

from £189 / night

£1136 - £1400 / week

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from £189 / night

14

Farmhouse letting in Localita Mucchia with shared pool

Cortona / Localita Mucchia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sleeps: 2+1 – 72sq. Meters (775 sq. Ft) This charming 1 bedroom first floor apartment rentals in Tuscany, has an open living area leading to a covered private terrace with great views of Chiana Valley and Cortona. It has a fully equipped kitchen leading to a doub  …see more

from £115 / night

£794 / week

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from £115 / night

5

Province of Arezzo / Cortona

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £69 / night

£479 / week

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from £69 / night

(3) Excellent 

43

Holiday home in Cortona

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
Villa Rosa is a private home nestled in the hillside of the historic and vibrant hill top town of Cortona. A few minutes drive or a leisurely stroll into the City of Cortona, with expansive views over the valley to the distance shores of Lake Trasimeno Villa Rosa is  …see more

from £245 / night

£1645 - £2023 / week

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from £245 / night

31

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • 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 £40 / night

£272 - £430 / week

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from £40 / night

27

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
it is the ideal place if you are looking to relax, private pool, and beautiful view.  …see more

from £89 / night

£623 - £904 / week

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from £89 / night

35

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £188 / night

£1316 - £2106 / week

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from £188 / night

(1)  

100

Cignano holiday apartment accommodation

Cortona / Cignano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
This agriturismo features a large outdoor pool and has seven apartments that can accommodate between 2 and 8 people.  …see more

from £79 / night

£553 - £829 / week

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from £79 / night

19

Holiday villa in Montalla

Cortona / Montalla

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Orlandicchio is a small villa built in stone, and completely restored in 2014. Located on top of a hill from which you can admire the stunning view of the “valle”, it has its own private entrance, parking, garden and swimming pool (4m x 8m). The hous  …see more

from £234 / night

£1632 - £2939 / week

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from £234 / night

100

Holiday apartment in Cignano

Cortona / Cignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
This agriturismo features a large outdoor pool and has seven apartments that can accommodate between 2 and 8 people.  …see more

from £101 / night

£584 - £860 / week

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from £101 / night

24

Cortona holiday home rental

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Independent stone house at the foot of Cortona with swimming pool, garden  …see more

from £157 / night

£1097 / week

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from £157 / 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 £269 / night

£1882 - £2808 / week

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from £269 / night

28

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

 …see more

from £84 / night

£536 - £755 / week

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from £84 / night

9

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Torre Suite is located on the first floor. Very large, light and airy bedroom with wonderful views of the garden and hills around; king size double bed and a sofa bed making it an ideal apartment for a couple or small family wishing to contain their costs. Large marble-  …see more

from £66 / night

£435 - £483 / week

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from £66 / night

100

Holiday apartment in Cignano

Cortona / Cignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
This agriturismo features a large outdoor pool and has seven apartments that can accommodate between 2 and 8 people.  …see more

from £66 / night

£369 - £584 / week

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from £66 / night

28

Cortona / Poggioni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £119 / night

£615 - £1036 / week

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from £119 / night

(1) Excellent 

34

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

6 15 Min stay varies

  • 6 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Old Farmhouse "Agriturismo Henni" of 1800th totally renovated with antiseismic criteria in 2016, with swimming pool 6mt x 12mt, hydromassage and sauna with panoramic view. The building is situated upper the hill, around the house there is and olive grove, vine  …see more

from £395 / night

£2632 - £3948 / week

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from £395 / night

31

Cortona / Montanare

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly

 …see more

from £62 / night

£351 - £527 / week

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from £62 / night

24

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Exquisite Tuscan holiday villa, originally built in the 15th Century but lovingly restored in the last 7 years, overlooking lush green rolling hills within a short distance of magical Cortona, the jewel in the Tuscan crown. Set in 30 acres of unspoilt National Park co  …see more

from £229 / night

£1600 - £2000 / week

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from £229 / night

8

Holiday home rental

Cortona / Montanare

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Argella is a little country village all built in sand-stone, part of an old agricultural area. In the property there are two independent apartments. Argella is close to Cortona , an etruscan city rich in monuments and cultural life  …see more

from £71 / night

£439 - £650 / week

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from £71 / night

13

Holiday farmhouse with shared pool in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
A lovely vacation home for 2 people or a family of 4. A charming and spacious sitting room converted from the Old Flour Mill with the original millstone. All the comforts of home in the fully fitted kitchen. Try out your Tuscan cooking skills or plan an evening barbecue  …see more

from £88 / night

£579 - £698 / week

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from £88 / night

100

Cortona holiday apartment rental

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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

7

Cortona / Pietraia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £108 / night

£662 - £2136 / week

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from £108 / night

100

Cignano holiday apartment let

Cortona / Cignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
This agriturismo features a large outdoor pool and has seven apartments that can accommodate between 2 and 8 people.  …see more

from £97 / night

£553 - £829 / week

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from £97 / night

13

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £71 / night

£492 / week

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from £71 / night

24

Cortona / Montanare

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly

 …see more

from £71 / night

£483 - £571 / week

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from £71 / night