Walking holiday villas and apartments Cortona | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona
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  • Fratticciola (1)
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  • Mercatale di Cortona (12)
  • Montalla (4)
  • Montanare (6)
  • Montecchio (10)
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209 Holiday homes

Filters applied: Walking holidays (209)

(32) Excellent 

21

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 £203 / night

£1423 - £2544 / week

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from £203 / night

(1) Excellent 

4

Villa Sonia, Cortona Tuscany - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Sonia is for sure, a really special property tucked away on the sleepy hillside of Cortona and, just a short distance form the enchanting franciscan monastery of Le Celle. Villa Sonia is perfect for four to 12 guests.This ancient stone farmhouse dates back to the  …see more

from £209 / night

£1457 - £1465 / week

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from £209 / 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 £518 / night

£3449 / week

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from £518 / 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 £78 / night

£518 - £1057 / week

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from £78 / 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

£647 - £733 / week

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from £87 / 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 £148 / night

£1035 - £1294 / week

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from £148 / 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 £39 / night

£272 / week

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from £39 / night

24

Villa Margherita Tre - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Located in a true oasis of peace and tranquillity, Villa Margherita Tre is a sweet indipendent villa with private pool offering breathtaking views over the hills surrounding the sought after town of Cortona as well as unbeatable value for money. With 2 bedrooms, 2 bathr  …see more

from £35 / night

£242 - £1044 / week

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from £35 / 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 £86 / night

£561 - £819 / week

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from £86 / 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 £61 / night

£397 - £432 / week

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from £61 / 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 £104 / night

£690 - £1026 / week

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from £104 / 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 £150 / night

£1048 - £1419 / week

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from £150 / 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 £145 / night

£1009 - £3138 / week

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from £145 / 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 £69 / night

£453 - £496 / week

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from £69 / 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

(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 £214 / night

£1492 - £3276 / week

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from £214 / 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 £138 / night

£737 - £1405 / week

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from £138 / night

(2) Excellent 

12

Charming Cortona villa with private pool (Dardano) - Cortona villa sleeps 6

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

(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 £78 / night

£544 / week

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from £78 / 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 £419 / night

£2932 - £4656 / week

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from £419 / night

(11) Excellent 

35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

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 style villa recently restored 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 doorstep. Tran  …see more

from £65 / night

£475 / week

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from £65 / 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

(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

(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

£518 - £776 / week

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from £87 / 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

£440 - £500 / week

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from £65 / night

7

Apartment in Sant 'Angelo di Cortona - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Apartment Sant' Angelo in Cortona is a bright and spacious one bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in typical Tuscan style, full of character, offering guests a warm vacation home.The ap  …see more

from £87 / night

£604 / week

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from £87 / 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 £52 / night

£345 / week

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from £52 / 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 - £1883 / week

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from £235 / night

18

Rustic two bedroom Tuscan apartment close to Cortona's main square, wifi and parking available - Cortona apartment sleeps 2

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
Quintani Sole - central apartmentApartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square a  …see more

from £69 / night

£432 / week

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from £69 / 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 £65 / night

£432 - £475 / week

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from £65 / 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 £169 / night

£733 - £1117 / week

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from £169 / 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 £95 / night

£651 - £755 / week

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from £95 / 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 - £1883 / week

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from £235 / night

13

Cortona / Montecchio

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from £128 / night

£897 - £1233 / week

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from £128 / 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 £135 / night

£1645 - £1883 / week

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from £135 / night

(5) Excellent 

14

Borgo di Vagli - Mercatale di Cortona house sleeps 6

Cortona / Mercatale di Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
Located in the heart of the Tuscan countryside, Borgo di Vagli is a quaint, meticulously restored 14th century Hamlet surrounded by a protected area of olive groves, fruit trees and ancient oaks. From the terraces, you can enjoy panoramic views of the breathtaking Tusca  …see more

from £113 / night

£647 - £819 / week

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from £113 / 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 - £1883 / week

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from £235 / night

24

Villa Fonte - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Fonte is located in an extraordinary panoramic position in the open countryside surrounded by olive trees and other typical Tuscan plants but within walking distance from the famous historical town of Cortona just 400 meters away. The perfect place for a holiday d  …see more

from £413 / night

£2888 - £4483 / week

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from £413 / night

(1) Excellent 

31

ANTICO PALLAIO - Cortona villa sleeps 9

Province of Arezzo / Cortona

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
tipical old house, swimming pool, wifi, tv satelite,bbq, volley ball field, pétanque field, mini tennis field. beatiful wiew over the chiana valley. all the old charme of tuscany. 4bedroom, 4 bathroomLocated in the village of Ossaia ( 3 km from Cortona), the property  …see more

from £259 / night

£1725 / week

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from £259 / 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 £296 / night

£2069 - £3535 / week

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from £296 / 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
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

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