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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona

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  • Bagnolo (3)
  • Cantalena (1)
  • Capezzine (3)
  • Cegliolo (3)
  • Centoia (7)
  • Farinaio (4)
  • Fratticciola (7)
  • Localita Mucchia (2)
  • Mercatale (2)
  • Mercatale di Cortona (14)
  • Montalla (5)
  • Montanare (9)
  • Montecchio (9)
  • Montecchio, San Lorenzo (2)
  • Poggioni (2)
  • Ruffignano (1)
  • Teverina (4)

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378 Holiday homes

Filters applied: Non-Smoking property (378)

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

(1) Excellent 

1 / 31

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £197 / night

£1375 - £2338 / week

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from £197 / night

(22) Excellent 

1 / 16

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Pets welcome;
 …see more

from £75 / night

£384 - £642 / week

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from £75 / night

1 / 24

35753-Holiday house Lake Trasi - Mercatale villa sleeps 15

Tuscany / Province of Arezzo / Cortona / Mercatale

7 bedroomsSleeps 157 nights min stay

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Farmhouse surrouned by the green Umbria countryside,<br>bordering on Tuscany. The farmhouse is divided in 3, intereconnected,<br>apartments, accommodating in total 15 persons, with 3 bathrooms of which one<br>with bath tub, 6 double bedrooms, 1 bedroom  …see more

from £161 / night

£1123 - £2099 / week

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from £161 / night

Featured properties

(4) Excellent 

1 / 47

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 47 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £115 / night

£805 - £1462 / week

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from £115 / night

(1) Excellent 

1 / 14

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 32 km; Ask owner if suitable for children;
 …see more

from £59 / night

£417 / week

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from £59 / night

(7) Excellent 

1 / 13

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Car not necessary; No pets allowed;
 …see more

from £80 / night

£0 / week

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from £80 / night

1 / 100

Residence Valdichiana - 3 pax - Cortona apartment sleeps 3

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
3 pax Guests at this apartment for rent in Tuscany afford the use of their own private garden. This apartment affords a living room with dining area, a fully fitted kitchen corner. Its accommodation capacity is for 3 people as it has a double bedded room and a sing  …see more

from £75 / night

£525 - £659 / week

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from £75 / night

(5) Very Good 

1 / 44

La Mimosa at La Lombarda - Centoia apartment sleeps 3

Tuscany / Province of Arezzo / Cortona / Centoia

1 bedroomSleeps 34 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 118 km; Swimming pool;
La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes i  …see more

from £63 / night

£417 - £542 / week

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from £63 / night

(17) Excellent 

1 / 24

Tuscany / Province of Arezzo / Cortona / Montecchio, San Lorenzo

2 bedroomsSleeps 71 night min stay

  • 2 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £38 / night

£0 / week

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from £38 / night

1 / 20

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; No pets allowed;
 …see more

from £99 / night

£689 - £928 / week

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from £99 / night

1 / 18

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Ask owner if suitable for children; Pets welcome;
 …see more

from £85 / night

£596 - £954 / week

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from £85 / night

1 / 24

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £272 / night

£1902 - £3532 / week

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from £272 / night

1 / 100

Curtum - Three-Room - Cortona apartment sleeps 4

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
These 2 three-roomed apartments can sleep up to 4 people each; and they both boast their own private bathroom with shower and full kitchenette. They also afford one double bedroom and one twin bedroom.Both apartments have their own private outdoor area, and they are equ  …see more

from £183 / night

£716 - £950 / week

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from £183 / night

(1) Excellent 

1 / 13

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £63 / night

£409 - £467 / week

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from £63 / night

1 / 69

Tuscany / Province of Arezzo / Cortona

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £405 / night

£2834 - £4959 / week

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from £405 / night

1 / 27

Sopra di Brena - Teverina farmhouse sleeps 8

Tuscany / Province of Arezzo / Cortona / Teverina

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 £171 / night

£1192 - £1550 / week

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from £171 / night

1 / 33

La Certosa - Cortona villa sleeps 10

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Description: A spacious farmhouse located in a spectacular, private and tranquil hillside setting that includes 15 acres of terraced olive groves and fruit trees (pears, plums, cherry and apple.) Cortona, with its shops, restaurants and open air market is a 20-minute wa  …see more

from £477 / night

£3334 - £4209 / week

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from £477 / night

(8) Excellent 

1 / 55

Il Bocciolo at La Lombarda - Centoia apartment sleeps 3

Tuscany / Province of Arezzo / Cortona / Centoia

1 bedroomSleeps 34 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 118 km; Swimming pool;
La Lombarda, our beautifully restored traditional 18th century Tuscan farmhouse is ideally placed within easy reach of Tuscany and Umbria's wealth of art and cultural centres. Cortona, nestling in its hillside just 20 minutes away, with its medieval cobbled lanes i  …see more

from £67 / night

£438 - £563 / week

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from £67 / night

1 / 100

Curtum - Two-Room - Cortona apartment sleeps 3

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 31 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
These 2 two-roomed apartments sleep up to 3 people each; and they both boast their own private bathroom with shower and full kitchenette. They also afford a double bedroom and another space to sleep another person.Both apartments have their own private outdoor area, and  …see more

from £141 / night

£525 - £600 / week

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from £141 / night

(8) Excellent 

1 / 29

Villa Rosa: Tuscan dream home in the hills with private pool, terrace and garden

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: 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 in beautiful Tuscany. Within a few minutes drive or a leisurely stroll into the City of Cortona and coupled with expansive views over the valley to the distance  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

1 / 30

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £422 / night

£2950 - £4700 / week

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from £422 / night

1 / 29

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Not suitable for children; Car essential; Some pets are welcome - please contact the owner;
 …see more

from £95 / night

£659 - £880 / week

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from £95 / night

1 / 53

Villa San Pietro - Cegliolo villa sleeps 10

Tuscany / Province of Arezzo / Cortona / Cegliolo

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
This stunning villa is located 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 with tra  …see more

from £286 / night

£2000 - £3417 / week

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from £286 / night

1 / 24

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £122 / night

£850 - £1849 / week

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from £122 / night

1 / 100

Nina - Cortona villa sleeps 4

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Great for children of all ages ;
ExteriorsThis beautiful and secluded villa lies in Cortona's countryside, with spectacular views over the valley, Cortona and Trasimeno Lake. Located only a couple of minutes from the town center, it is also very close to the most famous art cities in the world, wh  …see more

from £215 / night

£1500 / week

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from £215 / night

1 / 31

Il Castagno, splendid tuscan villa among vineyards

Tuscany / Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
Villa Il Castagno is the heart of the wine estate of the same name, which is located in enchanting hilly position among vineyards and olive groves and from which one can catch sights of the evoking shape of the near town of Cortona. Guests will have the chance to stay i  …see more

from £342 / night

£2375 - £3750 / week

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from £342 / night

1 / 101

I Girasoli - 4+2 pax - Cortona apartment sleeps 6

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Nearest beach 130 km; Swimming pool; Great for children of all ages ;
This 90sq-m apartment hosting 4+2 (6 guests) near Cortona is perfect to absorb Tuscan lure. It concentrates Tuscan style in its terracotta floor, its wooden ceiling which kept its structure like in the old times. The first thing guests find as they are entering  …see more

from £67 / night

£417 - £459 / week

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from £67 / night

1 / 100

Cortona 62608 - Cortona villa sleeps 4

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Beautiful country house in stone which has recently been restored, in a very peaceful and quiet location with scenic views, ca. 20km from Cortona and Lake Trasimeno. The house has been transformed into a welcoming and comfortable country residence, maintaining the typic  …see more

from £157 / night

£1095 - £1847 / week

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from £157 / night

1 / 35

Casa Fontelunga, ancient tuscan villa with pool

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Casa Fontelunga is a lovely country house placed in an enchanted location hillside, between our olive plantation and just a few minutes from the beautiful art city of Cortona, made famous worldwide from the book and movie 'Under the Tuscan Sun'.Privacy and qui  …see more

from £193 / night

£1125 - £1875 / week

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from £193 / night

1 / 12

Col di leccio, beautiful panoramic stone cottage

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Car essential;
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 £180 / night

£1250 - £2084 / week

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from £180 / night

1 / 25

Tuscany / Province of Arezzo / Cortona

4 bedroomsSleeps 97 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £226 / night

£2042 - £2917 / week

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from £226 / night

(1) Excellent 

1 / 32

Tuscany / Province of Arezzo / Cortona

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £178 / night

£1246 - £2240 / week

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from £178 / night

(5) Excellent 

1 / 24

Gorgeous five bedroom villa, game room, outdoor p

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
The Cortonese hillside, La Fortezza and the ancient wall which encloses the town, dominate the view of the surrounding hillside.Guests have exclusive use of the delightful 12x6 swimming pool, with Roman steps, which lies in an extremely panoramic position and from where  …see more

from £140 / night

£975 - £3034 / week

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from £140 / night

(27) Excellent 

1 / 31

Holiday apartment under the Tuscan sun, sleeps 4

Tuscany / Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
This charming apartment, made of stones, consists of bedroom with queen size bed and a big wardrobe/closet, living room with a convertible sofa-bed and a breath taking view of the Val di Chiana Valley, full kitchen with dish washer, breakfast table and the same beautifu  …see more

from £88 / night

£492 - £650 / week

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from £88 / night

1 / 30

Tuscany / Province of Arezzo / Cortona

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £328 / night

£2292 - £3209 / week

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from £328 / night

1 / 22

Piccola Bramasole - Cortona villa sleeps 4

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Great for children of all ages ; No pets allowed;
Name: PICCOLA BRAMASOLEAccommodation: VilleLocation: CORTONA Sleep: 4 Bedrooms: 2 Bathrooms: 2Booking Condition:rentals go from saturday to saturday Arrivals from 4 to 7 pm Departure within 10 amExtra costs:Final cleaning is included. Air conditioning is included Intern  …see more

from £279 / night

£1950 - £3034 / week

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from £279 / night

1 / 19

Wonderful traditional Tuscan a - Cortona apartment sleeps 6

Tuscany / Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
'Vecchio Frantoio' is a bright and spacious air-conditioned two-bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in the Tuscan manner add to the character of this comfortable and beautiful apart  …see more

from £117 / night

£750 - £992 / week

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from £117 / night

(5) Excellent 

1 / 4

Tranquil villa in Tuscan town of Cortona with private pool, terrace and nearby golf course

Tuscany / Province of Arezzo / Cortona

4 bedroomsSleeps 77 nights min stay

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This is a place to enjoy an authentic Tuscan experience. Close to the historic town of Cortona and set in acres of olives and pastures - this beautiful 17th century newly renovated Mill House with private pool has been painstakingly restored and provides an authentic t  …see more

from £229 / night

£1600 - £2140 / week

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from £229 / night

(2) Excellent 

1 / 25

Casa Gorgacce - Mercatale di Cortona house sleeps 6

Tuscany / Province of Arezzo / Cortona / Mercatale di Cortona

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 22 km; Swimming pool; Great for children of all ages ;
Casa Gorgacce is an old stone farmhouse with lots of character beautifully converted with all modern comforts. It has a private garden and pool, complete privacy yet with great access and only a few kilometres from 2 lively villages; Meratale di Cortona and Lisciano Nic  …see more

from £130 / night

£822 - £1488 / week

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from £130 / night

1 / 32

Tuscany / Province of Arezzo / Cortona

5 bedroomsSleeps 97 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £236 / night

£1650 - £2482 / week

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from £236 / night

Top Destination reviews

Villa Sonia, Cortona Tuscany
Good large home and easy for Cortona and other Tuscany places

For our extended family vacation -,this was more than perfect! The main villa with its three bedrooms and then the private annex which our parents enjoyed - gave us complete flexibility as well as the large gardens, pool and large eating terrace. … see more
To Stones
Amazing Home Away From Home

The best first impression was to be greeted late at night by Ester and her partner in the dark and in poor weather just so we could find a parking spot and get situated in the property. Ester was amazing and has gone to great lengths to ensure her ho … see more
Stunning Tuscan villa with five bedrooms, private
A true TUSCAN experience. Better than words can describe.

It is quite a challenge to put into words a description of this place, the family and the amazing time we had at Vila Papale. The house and the entire property has so much history and character making this place a unforgettable experience. The garden … see more
villa ai cedri
A marvellous house with a beautiful panorama view

A beautiful house in a peaceful area with a wonderful view to the valley. There are lovely rooms with tasteful furniture. Although the owners live next door, they do not disturb at all, they are really friendly and helpful any time you need somethin … see more
Rustic Tuscan farmhouse in the town of Cortona with gorgeous views, swimming pool, private garden and barbecue
Perfect!

This place is special. Its almost like a time machine. You can easy picture life way back in the old days, but at the same time you have a modern kitchen, pool, nice bathrooms The house was clean and in good condition. We (family of 5 ) stayed i … see more
Six bedroom traditional Tuscan villa in Cortona, a
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 bruschetta served to us on the night of arriv … see more

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