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

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Cortona

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575 Holiday homes

Filters applied: Swimming pool (605)

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

(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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(1) Excellent 

16

Capezzine holiday apartment rental

Cortona / Capezzine

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
The Villa is very well situated: in the middle of the most beautiful countryside of Tuscany and Umbria (scenic road), overlooking some of the most famous wineries of the “Vino Nobile of Montepulciano” (Avignonesi) and just minutes away from the most importan  …see more

from £106 / night

£746 / week

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from £106 / night

25

Province of Arezzo / Cortona

20 30 2 nights min

  • 20 bedrooms
  • Sleeps 30
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £136 / night

£851 / week

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from £136 / night

101

Apartment rental in Cortona with shared pool

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
These apartments near Cortona offer living area with sofa bed and kitchen corner, double and twin bedrooms with bathroom with shower. They host up to 6 or 7 people.  …see more

Pricing unknown

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Pricing unknown

(8) Very Good 

20

Holiday villa in Mercatale di Cortona

Cortona / Mercatale di Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 23 km
  • Swimming pool
  • Child friendly
Beautiful 800 year-old hilltop villa with stunning views , 4 bedrooms (sleeps 10) and private 12m x 6m pool. On border of Tuscany and Umbria, perfect for exploring local area. Fully restored, the house exudes character. ideal for large groups and families.  …see more

from £122 / night

£849 - £1999 / week

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from £122 / night

78

Holiday home with shared pool in Montecchio

Cortona / Montecchio

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stalla Cottage is an incredibly romantic, detached cottage with one bedroom + 1 bathroom. It opens onto a private garden with ecstatically beautiful views across the valleys that undulate into a depthless abyss of olive groves, orchards, honey fields of yellows, reds an  …see more

from £13 / night

£88 - £615 / week

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from £13 / night

24

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £207 / night

£1448 / week

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from £207 / 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 £752 / night

£5264 - £7018 / week

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from £752 / night

14

Cortona / Montecchio

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £53 / night

£268 - £343 / week

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from £53 / night

11

Cortona / Montanare

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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(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

24

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa Vaglie is a quaint cottage that is set in a charming and panoramic position, with completely authentic surroundings. Villa Vaglie is located next to the farmhouse where the owner and his family reside.  …see more

from £439 / night

£2018 / week

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from £439 / night

(3) Excellent 

25

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £188 / night

£1316 - £1755 / week

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from £188 / night

95

Montecchio holiday home rental

Cortona / Montecchio

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cerro + Castagna Cottage make up one extremely large apartment with a covered terrace/verandah - seats 6. Not only are there 2 double bedrooms + 2 bathrooms, there are also 2 sitting/dining rooms, each with a fully fitted kitchen, one of which is very large with a firep  …see more

from £113 / night

£790 - £965 / week

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from £113 / night

19

Province of Arezzo / Cortona

15 30 Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £746 / night

£4211 - £9343 / week

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from £746 / 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 £239 / night

£1667 / week

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from £239 / 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 £132 / night

£746 / week

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from £132 / 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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(11) Excellent 

35

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

7 24 3 nights min

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min
  • Nearest beach 250 km
  • Swimming pool
  • Child friendly
Villa Nobile is a stunning 19th Century classical villa recently restored farmhouse 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 doors  …see more

from £571 / night

£3992 / week

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from £571 / night

16

Holiday home with swimming pool in Cortona

Province of Arezzo / Cortona

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Family friendly villa Villas in Tuscany for groups  …see more

from £308 / night

£2150 - £3071 / week

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from £308 / 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 £44 / night

£308 - £5299 / week

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from £44 / 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

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

26

Holiday villa rental

Cortona / Montecchio

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in a beautiful hilly position, Il Giardino di Diana is a genuine stone and brick farmhouse surrounded by the characteristic Tuscan hills with olive groves and vineyards. Both the pool and the attic, boast spectacular panoramic views of the countryside with Corto  …see more

from £251 / night

£1755 - £3071 / week

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from £251 / night

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

42

Villa accommodation in Cortona with swimming pool

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa di Costantino is a typical Tuscan stone built manor, surrounded by a large garden and located in a beautiful spot at the bottom of the hill of the Etruscan old town of Cortona that offers outstanding views over the Valdichiana. The house is spacious and welcoming,  …see more

from £195 / night

£1360 - £2457 / week

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from £195 / night

33

Cortona holiday villa rental

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
the innovative techniques for sustainable constructions intended to protect the environment.  …see more

from £276 / night

£1930 - £2588 / week

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from £276 / night

23

Villa rental in Pietraia with swimming pool

Cortona / Pietraia

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 155 km
  • Swimming pool
  • Child friendly
In the verdant countryside in the heart of Tuscany close to Cortona, is located Villa Capezzine, which is a cosy retreat for your holidays in complete quiet and relaxation. The villa is bright and luminous furnished in keeping with the typical Tuscan style but with mod  …see more

from £113 / night

£790 - £1404 / week

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from £113 / night

(16) Excellent 

46

Home rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 10 3 nights min

  • 6 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“heaven on hearth” I stayed with a group of friends in this beautiful Tuscan farmhouse. We had such a great time. The house is full of charm and character and soo cool during hot summer afternoons, just heaven. The sourrounding areas are just stunni  …see more

from £158 / night

£965 - £1316 / week

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from £158 / night

28

Holiday home with shared pool in Cortona

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cottage I Frati lies at the foot of the Cortona hill, just a few minutes drive from the famous Etrsucan town praised by Frances Mayes in her “Under the Tuscan Sun”. The estate is made up of a main house and Cottage I Frati. The owner, a famous pediatrician,  …see more

from £161 / night

£1123 - £1737 / week

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from £161 / night

16

Cortona holiday apartment rental

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in Cortona with 1 bedrooms sleeps 2  …see more

from £48 / night

£277 - £395 / week

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from £48 / night

19

Holiday apartment in Cortona

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Cortona with 3 bedrooms sleeps 6  …see more

from £116 / night

£684 - £1141 / week

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from £116 / 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

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

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

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

25

Holiday home with swimming pool in Cortona

Province of Arezzo / Cortona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Nestled deep within the hills of Tuscany yet only 500 metres from all the attractions of Cortona, this comfortable house is an ideal retreat for 4 nature-loving or wine-loving holidaymakers. Inside the house, the lounge is perfect for unwinding after a day of explorat  …see more

from £84 / night

£454 - £793 / week

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from £84 / night

52

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 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 £274 / night

£1917 - £3171 / week

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from £274 / night