Long term rentals Cortona | Holiday Lettings

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Cortona

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817 Holiday homes

35

Cortona / Bagnolo

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £257 / night

£983 - £2180 / week

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from £257 / night

(25) Excellent 

16

Province of Arezzo / Cortona

2 4 Min stay varies

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

 …see more

from £60 / night

£359 - £684 / week

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from £60 / night

(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 £147 / night

£1026 - £1667 / week

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from £147 / night

(33) 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 £201 / night

£1411 - £2522 / week

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from £201 / 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 £112 / night

£389 - £569 / week

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from £112 / night

(1) Excellent 

19

Holiday apartment with shared pool 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 arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £59 / night

£409 - £552 / week

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from £59 / night

(4) Excellent 

13

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £65 / night

£419 - £479 / week

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from £65 / 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 £86 / night

£599 - £1048 / week

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from £86 / night

12

Holiday cottage with swimming pool in Cortona

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Col di Leccio is a beautiful property made up of two stone cottages which enjoy a wonderful hilly position, a few minutes from the medieval town Cortona. Each house consists of two floors which host a cosy siting room with sofa and tv, dining area, fully fitted kitchen,  …see more

from £184 / night

£1283 - £2137 / week

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from £184 / night

(1) Excellent 

20

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can also arrange special days or tours for;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £50 / night

£390 - £523 / week

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from £50 / night

(2) Excellent 

14

Province of Arezzo / Cortona

1 2 Min stay varies

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

 …see more

from £69 / night

£257 - £389 / week

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from £69 / night

14

Holiday apartment in Cortona

Province of Arezzo / Cortona

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
Apartments in historical center - Ville: La Piccionaia  …see more

from £342 / night

£2394 / week

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from £342 / night

(2) Excellent 

11

Holiday villa in Cortona

Province of Arezzo / Cortona

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Dardano is a deceptively large house, full of atmosphere. It is a simple country home, basic even, but with an elemental charm. You drive up to the house with its ancient stone well and to one side there's a little vine-covered area for shady outdoor eating. The garde  …see more

from £165 / night

£1150 / week

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from £165 / night

(1) Excellent 

12

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. It is perfect for wheel-chairs users. The kitchen is fully equipped and there is a dishwasher and a fireplace.La Stalla has also a tipical  …see more

from £86 / night

£513 - £770 / week

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from £86 / night

(2) Excellent 

19

Holiday apartment with shared 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
The Ciliego is situated on a Tuscan hill in a very peaceful spot that enjoys a breathtaking view of the Chiana Valley. It is an 18th century sand stone farmhouse built on two floors. Ground floor: comfortably furnished sitting room , fully equipped kitchen and dining ro  …see more

from £92 / night

£642 - £941 / week

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from £92 / night

19

Cortona holiday apartment let

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
The apartment Sant'Angelo is located just below the Etruscan City of Cortona in a beautiful residential complex which has been tastefully restored, maintaining the traditional characteristics of the antique oil mill that it once was. Video footage of apartment on Y  …see more

from £120 / night

£770 - £1018 / week

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from £120 / night

(5) Excellent 

20

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £43 / night

£257 - £411 / week

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from £43 / 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 £175 / night

£1223 - £1590 / week

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from £175 / 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 £65 / night

£436 - £496 / week

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from £65 / 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 Quintani, Is  …see more

from £65 / night

£411 / week

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from £65 / night

(1) Excellent 

27

Province of Arezzo / Cortona

3 6 Min stay varies

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

 …see more

from £85 / night

£556 - £812 / week

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from £85 / night

53

Holiday villa in Cegliolo

Cortona / Cegliolo

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa is located 2,5 km from Cortona. Recently renovated and nicely furnished, it is an 18th century Tuscan stone house. Surrounded by olive trees and facing south with lovely views across the valley below, Villa San Pietro is very private and quiet  …see more

from £294 / night

£2052 - £3505 / week

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from £294 / night

6

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

17

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Only 15 minutes from the villa you can easily access the Etruscan town of Cortona.  …see more

from £315 / night

£2200 - £3200 / week

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from £315 / night

(9) Excellent 

32

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
“Fabulous, breathtaking and relaxing - just the right place for a getaway.” The holiday was easy to arrange with good communication on location, directions etc. The villa was lovely and comfortable for our stay. You had the ability to dine inside or  …see more

from £245 / night

£1645 - £2028 / week

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from £245 / night

(1) Excellent 

53

Cortona holiday apartment rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Freshly renovated 2 bedroom/2 bathroom apartment with a private terrace overlooking the valley. It sleeps 6 people. We also have 4 more apartments right next door, if you see that this one won't be available on the calendar.  …see more

from £150 / night

£830 - £1069 / week

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from £150 / night

35

Cortona holiday villa rental

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
3 bedrooms Tuscan country villa in panoramic location with private swimming pool , private garden and parking . Five minutes away from the beautiful medieval city of Cortona and the famous cooking school I Gustasapori  …see more

from £198 / night

£1154 - £1924 / week

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from £198 / night

22

Holiday villa in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Villas in Cortona - Ville: PICCOLA BRAMASOLE  …see more

from £286 / night

£2000 - £3112 / week

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from £286 / night

10

Cortona holiday apartment rental

Province of Arezzo / Cortona

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Grecale is a part of the beautiful apartment complex, Poggio al Vento. The apartments are located in the same farmstead, which has been tastefully renovated to retain much of the original character and features. Ideal for a couple or a family, the apartments retain a wa  …see more

from £55 / night

£385 - £677 / week

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from £55 / 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 completely r  …see more

from £167 / night

£727 - £1278 / week

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from £167 / night

(9) Excellent 

38

Holiday cottage with swimming pool 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
“Tuscan Dream” I cannot say enough good things about this wonderful Tuscan Dream Villa. The owner Christine was on another continent went out of her way to make us feel at home and cater to our every need through email exchanges and her wonderful hou  …see more

from £245 / night

£1645 - £2023 / week

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from £245 / 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 £513 / night

£3419 / week

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from £513 / 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 £86 / night

£1112 / week

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from £86 / night

(2) Excellent 

20

Holiday apartment in Cortona

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Piero's organic vegetable garden delights guests' palate with seasonal produce: fruit, tomatoes, courgettes, green beans, lettuce, aromatic herbs. On request a skilled mountain-bike guide can accompany guests to discover stunning paths and trails, but even on  …see more

from £60 / night

£342 / week

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from £60 / night

(8) Excellent 

55

Holiday apartment in Centoia

Cortona / Centoia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
“Great base for discovering Tuscany.” Peter and Nina's apartments are in an ideal situation for exploring Tuscany with the added bonus of a pool to relax by when you return from trips to the surrounding hilltop villages. Il Boccolio is spacious and  …see more

from £69 / night

£479 / week

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from £69 / night

18

Holiday cottage in Cortona

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Acero is a cosy apartment that belongs to a beautiful hillside property, Col di Leccio, an authentic farmhouse where nature and silence dominate. Acero is made up of a double bedroom, a bedroom with twin beds, a bathroom with a shower, a kitchen and a living room. There  …see more

from £68 / night

£471 - £727 / week

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from £68 / night

(2) Very Good 

19

Holiday apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
We can arrange special days or tours such as;Wine TastingCookingCyclingPaintingWalkingWeddings  …see more

from £63 / night

£438 - £600 / week

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from £63 / night

30

Province of Arezzo / Cortona

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £573 / night

£2351 - £3291 / week

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from £573 / night

24

Holiday villa with swimming pool in Cortona

Province of Arezzo / Cortona

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Il Casone lies in the open countryside, a few minutes from Cortona. Immersed in a large garden, among the green olive trees and the delicate scent of the roses, this ancient farmhouse has been painstakingly restored and converted into 4 comfortable apartments, character  …see more

from £294 / night

£2052 - £2693 / week

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from £294 / night

(2) Excellent 

25

Mercatale di Cortona holiday home rental

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 22 km
  • Swimming pool
  • Child friendly
Charming stone farmhouse with original features. Perfect for family holidays. Private fenced pool, table tennis and Wifi Beautiful countryside views. Only 2 kilometres from a village with shops and restaurant. Sought after location on the Tuscany-Umbria border.  …see more

from £150 / night

£884 - £1550 / week

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from £150 / night

Top Destination reviews

Charming Cottage Near Cortona, Garden, 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

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