Short city breaks Cortona | Holiday Lettings UK

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Cortona

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113 Holiday homes

Filters applied: City breaks (113)

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

(2) Excellent 

21

Holiday farmhouse with swimming pool in Cortona

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
“Stunning views, lovely house, helpful owner.” Cortona is a very picturesque medieval town and this villa is a longish walk from the town itself up a very windy road. The house is only a few years old but built in the style of the old houses. It has la  …see more

from £151 / night

£1053 - £1711 / week

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from £151 / night

(34) Excellent 

25

Holiday villa rental

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £207 / night

£1448 - £2588 / week

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from £207 / night

16

Cortona holiday villa accommodation

Province of Arezzo / Cortona

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely small villa is located at 400 m from the charming town of Cortona It is situated in a wonderful panoramic position, surrounded by the typical Tuscan countryside and olive groves, in a perfect location for a lovely and relaxing holiday, yet with the advanta  …see more

from £101 / night

£702 - £1053 / week

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from £101 / night

(1) Average 

37

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Garibaldi is a finely furnished and welcoming apartment, located on the first floor of a historic building having the same name of the Piazza that leads into the promenade in the centre of Cortona. The architecture of each area is enhanced by the choice of tones and fur  …see more

from £88 / night

£658 - £878 / week

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from £88 / night

17

Province of Arezzo / Cortona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £71 / night

£264 - £400 / week

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from £71 / night

(9) Excellent 

18

Province of Arezzo / Cortona

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary

 …see more

from £62 / night

£404 - £439 / week

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from £62 / night

(1) Excellent 

83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £88 / night

£527 - £860 / week

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from £88 / night

(1) Very Good 

15

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 25 km
  • Child friendly
  • Car not necessary

 …see more

from £88 / night

£527 - £615 / week

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from £88 / 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 £106 / night

£702 - £1044 / week

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from £106 / night

(1) Excellent 

80

Province of Arezzo / Cortona

2 6 1 night min

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

 …see more

from £106 / night

£702 - £1044 / week

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from £106 / night

(19) Excellent 

24

Cortona / Montecchio, San Lorenzo

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £40 / night

£277 / week

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from £40 / night

29

Cottage rental in Pietraia with swimming pool

Cortona / Pietraia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, Il Nido is a lovely small villa recently restored and finely appointed with a contemporary country-chic style. The skillful ability in matching the soft tones and the tasteful reca  …see more

from £107 / night

£746 - £1755 / week

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from £107 / 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 £527 / night

£3509 / week

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from £527 / night

(2) Excellent 

27

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 135 km
  • Swimming pool
  • Child friendly
“Wonderful, true Italian experience"” Have stayed in many hotels and apartments all over the world and this was truly a 'stand-out.' From the moment our group of 8 arrived we were made to feel welcome by Manuela. Little, extra touches such as bruschett  …see more

from £396 / night

£2772 - £3579 / week

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from £396 / night

(5) Excellent 

42

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £66 / night

£461 / week

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from £66 / night

(1) Excellent 

14

Province of Arezzo / Cortona

2 4 Min stay varies

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

 …see more

from £115 / night

£400 - £584 / week

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from £115 / night

(1) Excellent 

27

Cortona / Farinaio

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £115 / night

£922 - £1097 / week

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from £115 / night

(2) Excellent 

88

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £106 / night

£615 - £1044 / week

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from £106 / night

(1) Excellent 

24

Apartment rental in Montalla with shared pool

Cortona / Montalla

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Equipped with chairs, shades, and beach beds.It has been restored with respect for the original stile and all the furniture are antique, you will have a warm and relaxing feeling when you enter Il Moro Novo.The house is located just outside a small country villa  …see more

from £62 / night

£322 - £608 / week

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from £62 / night

27

Teverina holiday farmhouse rental

Cortona / Teverina

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Sopra di Brena is located in San Pietro a Dame, about 20 kms from Cortona. The villa is an old restored farmhouse which enjoys stunning, panoramic views. It is surrounded by vinyards (around 1,350 Pinot Nero vines), which have been producing a highly-prized wine since  …see more

from £180 / night

£1255 - £1632 / week

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from £180 / night

(3) Very Good 

24

Holiday farmhouse with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 £158 / night

£1097 / week

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from £158 / night

(4) Very Good 

23

Holiday villa with shared pool in Cortona

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“The perfect base camp to travel around Tuscany” We stayed there for two weeks during the summer with our kids (6 and 2). The property is beautiful and very quiet, the view is amazing. The house was very old (about 400 years) but has just been renova  …see more

from £106 / night

£1141 / week

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from £106 / night

19

Holiday apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden
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 al  …see more

from £176 / night

£1185 / week

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from £176 / night

(12) Excellent 

35

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
“Our stay in this beautiful, fully equipped villa was amazing and the hospitality of the owners far exceeded expectations” The villa is beautifully decorated and the surrounding property and views are breathtaking. The owners live in the villa next do  …see more

from £226 / night

£1579 - £2544 / week

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from £226 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden

 …see more

from £88 / night

£615 - £1075 / week

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from £88 / night

(2) Excellent 

43

Holiday villa in Cortona

Province of Arezzo / Cortona

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Suitable for children age 5+
  • Private garden
Tuscany Cortona Ossaia Villa  …see more

from £53 / night

£351 - £720 / week

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from £53 / 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 £135 / night

£725 - £1208 / week

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from £135 / night

18

Apartment rental in Cortona

Province of Arezzo / Cortona

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Ask owner if suitable for children
Central apartment in the heart of Cortona, Tuscany, ideal for two person, cosy and quiet, near the best restaurant and grocery, shops and free parking. A perfect place to visiting Cortona and Tuscany tow like Arezzo, Siena, Firenze, Pienza, valdorcia, San Gimignano.<  …see more

from £71 / night

£439 / week

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from £71 / night

42

Province of Arezzo / Cortona

3 6 3 nights min

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

 …see more

from £70 / night

£483 / week

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from £70 / night

(1) Excellent 

15

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
"Luna" Apartment for 2 person, compose by one bedroom + kitchen + 1 bathroom with shower. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square and grocery. Palazzo Qui  …see more

from £66 / night

£422 / week

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from £66 / night

(1) Excellent 

24

Holiday studio in Cortona

Province of Arezzo / Cortona

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Child friendly
Welcome to Casale Il Granaio, a magic place in the heart of Valdichiana.In the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno lake and in the middle between the cities of Arezzo and Perugia. From here is easy also to reach Montepulciano, Sien  …see more

from £65 / night

£359 - £447 / week

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from £65 / night

(1) Excellent 

14

Home rental in Cortona with shared pool

Province of Arezzo / Cortona

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
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 marke  …see more

from £220 / night

£1312 - £1663 / week

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from £220 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £66 / night

£448 - £509 / week

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from £66 / night

(4) Excellent 

24

Holiday apartment in Cortona

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Child friendly
Welcome to “Casale il Granaio”, a magic place in the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno lake and in the middle between the cities of Arezzo and Perugia. From here is easy also to reach Montepulciano, Siena, Pienza, Rapolano an  …see more

from £72 / night

£439 - £558 / week

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from £72 / night

35

Cortona / Bagnolo

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £189 / night

£1321 / week

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from £189 / night

12

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden

 …see more

from £62 / night

£395 / week

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from £62 / night

(2) Excellent 

25

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £438 / night

£2544 - £4158 / week

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from £438 / night

(1) Excellent 

10

Holiday apartment in Cortona

Province of Arezzo / Cortona

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly
L'Etrusca e' un alloggio perfetto per chi vuole trascorrere le sue vacanze nel cuore della citta' e vivere direttamente la nostra tradizione<br />Near of the most important Tuscany and umbria Town like: Firenze, Arezzo, Montepulciano, Pienza, Monta  …see more

from £58 / night

£395 - £571 / week

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from £58 / night

(1) Excellent 

89

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 18 km
  • Swimming pool

 …see more

from £106 / night

£632 - £1044 / week

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from £106 / night

20

Province of Arezzo / Cortona

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £176 / night

£1141 - £2509 / week

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from £176 / night

Top Destination reviews

CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI
A Gem in Tuscany

The information provided by Cesare at the time of booking was the best we've ever had! On arrival, we were greeted with a very helpful introduction to "our home for the week". It was great having a welcome gift of wine, some delicious home grown plum … see more