Horse riding holiday villas and apartments Cortona | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Mercatale (1)
  • Mercatale di Cortona (9)
  • Montalla (4)
  • Montanare (6)
  • Montecchio (11)
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  • Teverina (1)

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222 Holiday homes

Filters applied: Horse riding (222)

(32) Excellent 

24

Tuscan Villa. Borgo Valecchie. Cortona - Montanare villa sleeps 10

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 £205 / night

£1435 - £2566 / week

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from £205 / night

(5) Excellent 

24

Gorgeous five bedroom villa, game room, outdoor p - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £146 / night

£1018 - £3166 / week

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from £146 / night

37

Garibaldi, splendid apt in the centre Cortona - Cortona apartment sleeps 6

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 £87 / night

£653 - £740 / week

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from £87 / night

(1) 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 £70 / night

£261 - £396 / week

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from £70 / night

(2) Excellent 

21

Villa Cicaleta within walking distance to Cortona - Cortona farmhouse sleeps 7

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
Surrounded by olive groves and a 3000sqm private garden, the fenced-in holiday villa offers absolute peace and quiet at only 1,5 kilometres from the Etruscan Cortona, which can be easily reached on foot. The Trasimeno lake with its nice beaches and islands is at 8km and  …see more

from £150 / night

£1044 - £1305 / week

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from £150 / night

16

Casina Vereno - Bagnolo villa sleeps 4

Cortona / Bagnolo

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This charming independent villa is situated in panoramic position in the Cortonese Mountains above the Etruscan hill town of Cortona. It's ideal location make it easy visit the most renowned historical and art cities of Tuscany and Umbria. The property, with privat  …see more

from £151 / night

£1057 - £1431 / week

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from £151 / night

10

Grecale - PI2012_226 - Cortona apartment sleeps 3

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 £56 / night

£392 - £688 / week

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from £56 / night

26

Cortona / Farinaio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £87 / night

£783 - £1044 / week

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from £87 / night

(12) Excellent 

21

Rustic Tuscan farmhouse in the town of Cortona with gorgeous views, swimming pool, private garden and barbecue - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
This charming Tuscan Farmhouse is set in a lovely, unspoilt region near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields. Casa Al Campo has 2 acres of unfenced land including its own private vineyard, two terraces and plenty of shaded seating  …see more

from £215 / night

£1505 - £3305 / week

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from £215 / night

(3) Very Good 

42

La Bozza , country apartment with private garden - Montalla apartment sleeps 8

Cortona / Montalla

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
Started officially as a busines in 1994 but with previous experience of property rental in the precedent 10 years, Agriturismo Fontelunga is now a reference poit for those searching for a true Tuscan experience.W own same of the nicest accommodation in the traditional  …see more

from £140 / night

£743 - £1417 / week

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from £140 / night

(8) Excellent 

55

Il Bocciolo at La Lombarda - Centoia apartment sleeps 3

Cortona / Centoia

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • 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 £70 / night

£457 - £500 / week

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from £70 / 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 £114 / night

£396 - £579 / week

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from £114 / night

(2) Excellent 

25

Casa Gorgacce - Mercatale di Cortona house sleeps 6

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 22 km
  • Swimming pool
  • Child friendly
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

£873 - £1550 / week

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from £130 / night

(2) Very Good 

53

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Ask about pets

 …see more

from £79 / night

£548 / week

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from £79 / night

(17) 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

£274 / week

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from £40 / night

(1) Excellent 

14

Luxury Tuscan Holiday Home , Stalla Rustica - Cortona house sleeps 8

Province of Arezzo / Cortona

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • 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 £250 / night

£1495 / week

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from £250 / night

(5) Very Good 

44

La Mimosa at La Lombarda - Centoia apartment sleeps 3

Cortona / Centoia

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • 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 £66 / night

£435 - £479 / week

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from £66 / night

(9) Excellent 

33

Villa Rosa - Heaven in Tuscany|Pool|WiFi|Cortona - Cortona villa sleeps 5

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
With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant Cortona. Couples love it, families love it. It is heaven. A two bedroom, two bathrooms, fully furnished beautiful  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(3) Excellent 

21

Tuscan Family Villa Castiglioni, Pool easy access - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 26 km
  • Swimming pool
  • Child friendly
This exceptional, luxurious and impeccable private estate in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Extraordinary views of both the famed Montechio Castle and, the Eternal Tuscan hill town of Castiglion Fiorentino can be easily  …see more

from £466 / night

£3256 - £4409 / week

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from £466 / night

(9) Excellent 

32

Cortona, Tuscan Retreat, Serene, WiFi, Pool, Bliss - Cortona house sleeps 5

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
Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close to the amenities but far enough away for privacy, seclusion and relaxation. We would love to welcome you to Villa Rosa w  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(1) Excellent 

24

Il Moro Novo - Montalla apartment sleeps 3

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 village, so i  …see more

from £61 / night

£320 - £603 / week

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from £61 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden

 …see more

from £79 / night

£522 - £1066 / week

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from £79 / night

(1) Excellent 

53

La Terrazza sulla Valle - Cortona apartment sleeps 6

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Beautifully freshly renovated 2 bedroom/2 bathroom apartment with a private terrace overlooking the Valley. Master bedroom with a big mirror closet, fireplace, stunning view of the valley from the window and access to private terrace. The other bedroom has a closet an  …see more

from £140 / night

£783 - £1087 / week

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from £140 / night

(1) Very Good 

22

Villino Laura - Montecchio villa sleeps 4

Cortona / Montecchio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 155 km
  • Swimming pool
  • Child friendly
Villino Laura is an old mill immersed in the picturesque green Tuscan countryside only few kilometres from Cortona and has been completely restored maintaining its original charm. The furnishing of this property makes it one of a kind for its class, due to its precious  …see more

from £136 / night

£792 - £1131 / week

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from £136 / night

(2) Very Good 

59

Charming 2 bedroom apartment in restored Tuscan farmhouse with pool located in historic Cortona - Centoia apartment sleeps 5

Cortona / Centoia

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
La Lombarda is our charmingly restored traditional 18th century Tuscan farmhouse. La Stufa is a charming two bedroom apartment with wood-beamed ceilings and terracotta floors. There is a comfortable sofa and two armchairs in the lounge, TV, DVD, books, games and videos  …see more

from £96 / night

£657 - £761 / week

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from £96 / night

(1) Excellent 

24

Beautiful villa with pool and amazing Tuscan view - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 161 km
  • Swimming pool
  • Child friendly
Villa Cortona is a beautifully restored luxury tuscan villa with 5 double bedrooms and 6 bathrooms.Each bedroom has its own different style and character and en-suite bathroom with wonderful views.The interior of Villa Cortona is large, bright and spacious, with two lar  …see more

from £423 / night

£2957 - £4696 / week

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from £423 / night

(6) Very Good 

51

Casa la Bozza, IL Bozzino - Montalla apartment sleeps 6

Cortona / Montalla

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
THE HOUSE IS SPLIT IN 2 INDEPENDENT APARTMENT OF THE SAME SIZE, BOT WITH A PRIVATE GARDEN, ENTRANCE AND PARKING, WE CAN RENT ONE OF THEM FOR 6+1 OR THE ENTIRE HOUSE FOR 12+2. THE DESCRIPTION BELOW REFERS TO Il Bozzino, the ground floor oneBUT APPLY TO BOTH. PLEASE READ  …see more

from £134 / night

£719 - £1198 / week

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from £134 / night

(5) Excellent 

30

Villa le Celle del Farinaio: Tuscan home with stunning valley views, swimming pool and trampoline, sleeps fourteen - Farinaio villa sleeps 14

Cortona / Farinaio

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
The cells of the villa Farinaio is situated in a beautiful hilly which overlooks the valley below and it is surrounded by green woods of our own property where you can find numerous hiking trails with different difficulty levels for taking a walk. The villa is completel  …see more

from £187 / night

£1305 - £2609 / week

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from £187 / night

(1) Excellent 

12

Villa Cuiano- La Stalla - Mercatale di Cortona apartment sleeps 4

Cortona / Mercatale di Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
If you take the road which follows the Tuscan-Umbrian border you come to Pierle, a medieval hamlet in the hills between Cortona and Lake Trasimeno, its castle dominating the verdant valley below.Here surrounded by olive groves and woodland of oaks and chestnuts, you wil  …see more

from £87 / night

£522 - £783 / week

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from £87 / night

53

Villa San Pietro - Cegliolo villa sleeps 10

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 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 £299 / night

£2087 - £3566 / week

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from £299 / night

(1) Excellent 

22

House in Central Cortona with Private Garden - Cortona cottage sleeps 6

Province of Arezzo / Cortona

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Our house is spacious and full of light - a perfect cool retreat after a warm summer day's exploration in Tuscany. Great for two love birds or a couple with a child, this accommodation in Cortona even has its own little walled garden, where you can sit and chat in  …see more

from £70 / night

£487 / week

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from £70 / night

(1) Very Good 

24

Villa Calcinaio - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
Awarded as one of the prettiest and most comfortable villas in Tuscany, Villa Calcinaio with its private swimming pool stands proudly in Cortona and offers amazing views over the Chiana Valley as well as the Church of "Santa Maria delle Grazie al Calcinaio", from which  …see more

from £68 / night

£474 - £600 / week

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from £68 / night

(9) Excellent 

38

Tuscan Dream|Private|Pool|Walk to Cortona|FreeWiFi - Cortona cottage sleeps 5

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
A dream home just for you. We created our home in Cortona with all the essential mod cons. Music, Kitchen, comfy beds, and of course with the essential pool and (FREE) Wi-Fi. Villa Rosa is nestled into the Cortona (Tuscan) hillside with only a few minutes drive to  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(10) Excellent 

24

villa ai cedri - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
"The agriturismo can accommodate 8 - 10 guests. The villa (250sqm) is set on the hillside and, from both the house and the gardens, one can enjoy the spectacular 180 degree views over the Valdichiana valley to the hills of Montepulciano beyond. The colours change throug  …see more

from £224 / night

£1566 - £2522 / week

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from £224 / night

20

Teresa Villa Overlooking a Breathtaking Landscape - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Teresa is a pretty villa with a wonderful view on Cortona valley, completely renovated and equipped with every comfort. Very near to the nice town of Cortona, this wonderful structure overlooks on a breathtaking landscape and it is situated short distance from a s  …see more

from £187 / night

£1305 - £2740 / week

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from £187 / night

(1) Excellent 

20

Le Casine - Lavanda Apartment - Fratta Santa Caterina apartment sleeps 3

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
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £50 / night

£390 - £523 / week

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from £50 / night

(2) Excellent 

20

Casa Anna, cosy holiday apartment Cortona - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Casa Anna is just a few km from the Etruscan-Medieval town of Cortona and offers a genuine and healthy holiday. It is situated in the hills area around Cortona (only 5 km from SR71 and 10 km from Cortona), in the heart of a small rural hamlet, and ensures guests real qu  …see more

from £53 / night

£348 / week

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from £53 / 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 £105 / night

£679 - £1035 / week

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from £105 / night

22

The Orangery: Cortona holiday villa with private pool and garden - Cortona villa sleeps 5

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 £170 / night

£740 - £1127 / week

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from £170 / night

(4) Excellent 

30

Tuscany, Cortona - Villa Under The Sun - Gorgeous - Cortona house sleeps 5

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
A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool and Wi-Fi connection, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vib  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / 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
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
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

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