50 Best Cortona Apartments on Holiday Lettings - Vacation rentals

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4,449 Vacation rentals

29

Mercatale Vacation villa rental

Cortona / Mercatale

6 11 7 nights min

  • 6 bedrooms
  • sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Max Weinberg, the long-time drummer for Bruce Springsteen's E Street Band, opens the doors of his marvellous holiday house situated in the gentle verdant hills between Tuscany and Umbria. Max and his wife bought their Tuscan home in 2000, succumbing to an infatuation wi …see more

from $467 / night

$3,269 - $4,509 / week

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from $467 / night

26

Cortona Vacation apartment rental

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
La Dolce Vita has been tastefully restored and decorated to the highest standards to produce a wonderful apartment in a quiet street a few minutes walk from the main square, bars and restaurants of Cortona. Picture windows in the living room and main bedroom provide stu …see more

from $136 / night

$958 - $1,127 / week

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from $136 / night

(11) Very Good 

Certificate of Excellence

46

Vacation apartment rental

Cortona / Centoia

1 3 4 nights min

  • 1 bedroom
  • sleeps 3
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 118 mi
  • 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 is a d …see more

Certificate of Excellence

from $102 / night

$710 / week

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Responds fast!
avg. 1 hour 59 minutes

from $102 / night

(11) Excellent 

57

Vacation apartment in Centoia

Cortona / Centoia

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 118 mi
  • 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 is a d …see more

from $108 / night

$754 / week

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avg. 1 hour 59 minutes

from $108 / night

24

Vacation 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 $324 / night

$2,267 - $3,854 / week

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from $324 / night

30

Vacation home with swimming pool in Cortona

Province of Arezzo / Cortona

6 11 7 nights min

  • 6 bedrooms
  • sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Il Giardino di Silvana is a typical Tuscan stone house located on an evocative hilly position, a few steps away from the prestigious Santa Maria Nuova church and walk to town. The property preserves its rustic style with cotto flooring, wood beamed ceilings and Pietra …see more

from $243 / night

$1,700 - $2,834 / week

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from $243 / night

18

Vacation villa rental

Province of Arezzo / Cortona

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
Villa San Martino is set in a delightful position among extensive grounds overlooking the countryside. The swimming pool is surrounded by olive trees and lush gardens. The nearest town is Cortona, famous for its ancient backgrounds, home town of famous painter Luca Sig …see more

from $201 / night

$1,406 - $2,551 / week

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from $201 / night

57

Vacation farmhouse with swimming pool in Creti

Cortona / Creti

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa La Rugantina, a typical Tuscan stone farmhouse finely restored, lies in the open countryside surrounded by wheat and sunflowers fields. The property boasts extended gardens and 6 large bedrooms: 5 doubles and a family room that sleeps 4. The whole house then can …see more

from $403 / night

$2,818 - $4,283 / week

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from $403 / night

21

Vacation 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
  • Pet friendly
Il Casone lies in the open countryside, a few minutes from Cortona towards Farneta. Immersed in a large garden, among the green olive trees and the delicate scent of the roses that frame the swimming pool area, this ancient farmhouse has been painstakingly restored and …see more

from $121 / night

$846 - $1,071 / week

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from $121 / night

(4) Excellent 

39

Cottage rental in Cortona

Province of Arezzo / Cortona

1 6 4 nights min

  • 1 bedroom
  • sleeps 6
  • 4 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
We rent occasionally and only for short periods, nice apartment with private garden area old town Cortona. 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 chil …see more

from $96 / night

$671 / week

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avg. 3 hours 14 minutes

from $96 / night

(9) Excellent 

16

Vacation apartment in Cortona

Province of Arezzo / Cortona

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
In Etruscan land, 3km from Cortona, beautiful apartment in a wonderful medieval village, with park and swimming pool, restored in Tuscan style, equipped with every comfort with free Wi-Fi in the garden, barbecue, deck chairs and private parking add no cost. The "Cloiste …see more

from $46 / night

$318 / week

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Responds fast!
avg. 39 minutes

from $46 / night

(2) Excellent 

17

Vacation 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
A luxury villa with private pool, Villa San Martino is set on a hill, high above the beautiful Niccone Valley on a quiet road, just 3 minutes from local village shops, restaurants and cafes. The position is a typically Tuscan, offering spectacular views from the house, …see more

from $408 / night

$2,855 / week

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from $408 / night

45

Vacation apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees. Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating …see more

from $90 / night

$624 / week

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from $90 / night

(54) Excellent 

23

Villa rental in Cortona with swimming pool

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 150 mi
  • Swimming pool
  • Child friendly
"The Cottage of Cortona", is a cozy holiday home set in the countryside in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in touch with nature ... Typical farmhouse, is located in the green heart of authentic Tuscany, in an area rich in h …see more

from $102 / night

$677 - $902 / week

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avg. 2 hours 48 minutes

from $102 / 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 $137 / night

$958 - $2,255 / week

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from $137 / night

(1) Excellent 

36

Vacation villa with swimming pool in Pietraia

Cortona / Pietraia

9 18 min stay varies

  • 9 bedrooms
  • sleeps 18
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The farm houses Sant'Anna offers its guests a recently renovated (2017), ideal for families and groups of friends. During the renovation special attention it was given to respect the architectural characteristics of the Tuscan houses, but will not sacrifice modern as th …see more

from $538 / night

$3,763 - $6,687 / week

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from $538 / night

15

Vacation villa in Cortona

Province of Arezzo / Cortona

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Villa with garden and barbecue, terrace overlooking the Val di Chiana and Lake Trasimeno in the distance. It is five minutes from the center of Etruscan Cortona and 1 hour from Perugia and Lake Trasimeno. Near Arezzo. The house is made of stone with rustic finishes, cei …see more

from $129 / night

$789 / week

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from $129 / night

(1) Excellent 

27

Vacation villa in Cortona

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly
This imposing two-storey villa is set in stunning grounds, which have the quality of a park. Here you can feel sheltered and secluded in each separate area, including that of the pool. The spaciousness of both the exterior and interior easily accommodates a large group. …see more

from $186 / night

$1,297 - $2,874 / week

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from $186 / night

28

Poggioni Vacation apartment rental

Cortona / Poggioni

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Its panoramic position and its peaceful isolation amongst the verdant mountains of Cortona make the farmhouse The Ladybug one of the most attractive accommodation facilities in the Cortona area and surroundings. The farm is located 11 miles away from Cortona into a posi …see more

from $167 / night

$1,167 / week

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from $167 / night

(2) Good 

37

Cortona Vacation 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 $114 / night

$850 - $964 / week

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from $114 / night

(28) Excellent 

33

Cortona Vacation apartment rental

Province of Arezzo / Cortona

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child friendly
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 $100 / night

$490 - $1,012 / week

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avg. 3 hours 43 minutes

from $100 / night

(1) Excellent 

19

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa La Pergola is an authentic private villa in Tuscany, very close to the Etruscan town of Cortona. La Pergola is situated in a cosy village consisting of two other villas each with private swimming pool. The patio, decorated with elegant garden furniture, has a scen …see more

from $282 / night

$1,691 - $3,551 / week

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from $282 / night

(16) Excellent 

46

Home rental in Cortona with swimming pool

Province of Arezzo / Cortona

6 10 3 nights min

  • 6 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
I Mandorli is an original Tuscan farmhouse. It has been refurbished using traditional materials and techniques to maintain it's rustic character and help stay cool through the long summer days. In autumn and winter you can relax in the spacious living room, in front o …see more

from $171 / night

$1,362 / week

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from $171 / night

(4) Very Good 

24

Vacation cottage with shared pool in Cortona

Province of Arezzo / Cortona

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Set in the parkland of ' Villa ' Baird, an aristocratic property which dates back to 1773 situated at the foot of the ancient Town of Cortona. The outhouse has been restored in keeping with it's original character and still has the original floors, wood beams, and open …see more

from $159 / night

$1,111 / week

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from $159 / night

42

Farinaio Vacation apartment rental

Cortona / Farinaio

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The apartment Girasole is situated on the ground floor and it has a separate entrance. It consists of: a living room, a kitchen, two bedrooms, two bathrooms with shower and independent heating. Apartment cleaning, detergents and waste: We use non-toxic cleaning products …see more

from $130 / night

$907 / week

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from $130 / night

(3) Excellent 

53

Cortona Vacation apartment rental

Province of Arezzo / Cortona

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 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 $136 / night

$733 - $1,511 / week

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avg. 3 hours 43 minutes

from $136 / night

(7) Excellent 

46

Vacation home 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 mi
  • 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 vibr …see more

from $351 / night

$2,452 / week

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Responds fast!
avg. 3 hours 38 minutes

from $351 / night

(14) Excellent 

57

Vacation 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 mi
  • 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 $351 / night

$2,452 / week

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Responds fast!
avg. 3 hours 38 minutes

from $351 / night

(8) Excellent 

26

Vacation villa rental

Cortona / Montecchio

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in a beautiful hilly position, Il Giardino di Diana is a genuine stone and brick farmhouse surrounded by the characteristic Tuscan hills with olive groves and vineyards. Both the pool and the attic, boast spectacular panoramic views of the countryside with Corto …see more

from $322 / night

$2,255 - $3,945 / week

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from $322 / night

(2) Very Good 

55

Vacation apartment in Cortona

Province of Arezzo / Cortona

1 6 4 nights min

  • 1 bedroom
  • sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Our freshly renovated 2 bedroom/1 bathroom apartment with a great patio (shared by our other apartment too). Casa dei Colori has all you need: Free WiFi, Air Conditioning, ceiling fans in the bedrooms, full kitchen with dishwasher, microwave, oven, blender, kettle, toas …see more

from $107 / night

$609 - $1,319 / week

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Responds fast!
avg. 3 hours 43 minutes

from $107 / night

(3) Very Good 

6

Cortona Vacation guest house rental

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Lovely cottage in the historic center of Cortona. Always our family's property was an ancient horse change station. in one of the walls is preserved the Manger hence the name.Restored with love is a typical Tuscan House: terracotta and wooden beams, brick arches and war …see more

from $115 / night

$631 / week

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from $115 / night

(6) Excellent 

27

Cortona Vacation cottage rental

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The search for a warm and welcoming Tuscan abode is over. Cottage Cortona Roccaio is a stone-clad home adjoined to another occupied house on a small family estate encircled by olive groves. From here, the alluring hill towns of Tuscany and Umbria are within easy reach. …see more

from $157 / night

$1,097 / week

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avg. 1 hour 17 minutes

from $157 / night

(9) Excellent 

43

Vacation apartment rental

Province of Arezzo / Cortona

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Three double rooms each with private bathrooms and showers, dining room, kitchen. In the garden a cabin with a wood oven, barbecue, table and chairs and deckchairs. From june 15 to august 31 the price per night includes air conditioning. In the kitchen ceiling fan. T …see more

from $79 / night

$553 / week

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Responds fast!
avg. 27 minutes

from $79 / night

(1) Excellent 

12

Vacation apartment with swimming pool in Mercatale di Cortona

Cortona / Mercatale di Cortona

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 12 mi
  • 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, …see more

from $136 / night

$947 / week

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from $136 / night

(1) Excellent 

83

Vacation apartment with shared pool in Cortona

Province of Arezzo / Cortona

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 18 mi
  • Swimming pool
  • Child friendly
La Fiorita-Farmhouse comprises separate 2 buildings: the manor house and an outbuilding. The apartment Glicine is on the annex building (ground floor) and is with a private garden and a own charming gazebo furnished for 4 holiday makers. The apartment is tastefully furn …see more

from $169 / night

$1,184 / week

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from $169 / night

(7) Excellent 

13

Vacation villa accommodation

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 15 mi
  • Child friendly
Our beautiful 16th century cottage is in an enviable location. The gardens with a private pool stretch out into views of the surrounding hillsides clad with olive groves, and vineyards. The nearby village of Pergo has bars, restaurants, and a supermarket. 10 minutes wil …see more

from $71 / night

$493 - $986 / week

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from $71 / night

(43) Excellent 

Certificate of Excellence

35

Vacation villa rental

Cortona / Montanare

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 180 mi
  • 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

Certificate of Excellence

from $215 / night

$1,691 - $3,325 / week

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Responds fast!
avg. 58 minutes

from $215 / night

(1) Excellent 

31

Villa rental in Cortona with swimming pool, golf nearby

Province of Arezzo / Cortona

3 11 3 nights min

  • 3 bedrooms
  • sleeps 11
  • 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 bathroom Located in the village of Ossaia ( 3 km from Cortona), t …see more

from $340 / night

$2,267 / week

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from $340 / night

(15) Excellent 

53

Vacation villa in Cortona

Province of Arezzo / Cortona

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • 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 p …see more

from $348 / night

$2,435 / week

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Responds fast!
avg. 3 hours 38 minutes

from $348 / night

(6) Excellent 

24

Vacation home with shared pool in Cegliolo

Cortona / Cegliolo

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 140 mi
  • Swimming pool
  • Child friendly
It is situated at the foot of Cortona Etruscan city famous. It is immersed in the green countryside and close to the archaeological etruschi Melone I and Melone II of Sodo. Major cities nearby include: Arezzo Montepulciano Siena Perugia Assisi Montalcino Pienza San Gim …see more

from $136 / night

$846 / week

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from $136 / night