50 Best Cortona Apartments on Holiday Lettings - Vacation rentals

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Cortona

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4,243 Vacation rentals

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 $131 / night

$801 / week

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from $131 / night

(39) Excellent 

Certificate of Excellence

16

Cortona Vacation home rental

Province of Arezzo / Cortona

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 150 mi
  • Child friendly
  • Pet friendly
My cozy 3-floor house is placed on top of the Etruscan walls of Cortona, at the edge of the historic center, on a very quiet and characteristic street. It can accommodate up to 4 guests. I hope you will enjoy the stunning view on the valley beneath! Caratteristica casa …see more

Certificate of Excellence

from $86 / night

$492 - $927 / week

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avg. 2 hours 2 minutes

from $86 / night

(3) Excellent 

10

Vacation apartment in Cortona

Province of Arezzo / Cortona

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Child friendly
  • Private garden
Wonderfully located only ten minutes walking from the city center of Cortona. From this property you will have one of the most beautiful views of the city, the valley and the lake Trasimeno.It is one apartment on the first floor of a villa, the owner live upstairs. The …see more

from $115 / night

$801 - $1,402 / week

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from $115 / night

(3) Very Good 

42

Vacation apartment with shared pool in Montalla

Cortona / Montalla

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 200 mi
  • 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 $187 / night

$978 - $1,841 / week

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avg. 2 hours 33 minutes

from $187 / 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 $123 / night

$859 - $1,087 / week

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from $123 / night

50

Vacation apartment rental

Cortona / Farinaio

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • 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 $119 / night

$836 / week

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from $119 / night

(2) Excellent 

27

Vacation lodge in Cortona

Province of Arezzo / Cortona

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The "Fattoria Borgonuovo" is located in an agricultural and hilly area of the Val di Chiana, very close to the beautiful and old town of Cortona, and a short distance from the most important historical and wine centers of the southern part of Tuscany, as, Montepulciano, …see more

from $75 / night

$515 - $744 / week

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Responds fast!
avg. 1 hour 19 minutes

from $75 / night

(5) 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 $137 / night

$854 / week

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from $137 / night

(1) Excellent 

24

Apartment rental in Montalla with shared pool

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 …see more

from $80 / night

$418 - $824 / week

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Responds fast!
avg. 2 hours 33 minutes

from $80 / 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 $139 / night

$967 - $2,275 / week

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from $139 / night

(9) Very Good 

20

Vacation villa in Mercatale di Cortona

Cortona / Mercatale di Cortona

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 23 mi
  • Swimming pool
  • Child friendly
Casaccia is a beautiful medieval house on a hilltop with a large private pool and gardens offering incredible views. Fully refurbished, the villa offers 4 large bedrooms (sleeping up to 10), and three bathrooms, including a delightful cottage in the garden with its own …see more

from $155 / night

$1,083 - $2,932 / week

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from $155 / night

5

Vacation apartment with shared pool in Pietraia

Cortona / Pietraia

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bright and spacious apartment of 110 square meters consisting of 2 beautiful and spacious double bedrooms, a large living room with fireplace and fully equipped kitchen; It has a large loft with tv-reading room and double bedroom, where you can enjoy moments of total re …see more

from $161 / night

$1,122 / week

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Responds fast!
avg. 1 hour 17 minutes

from $161 / night

(6) Very Good 

51

Apartment accommodation in Montalla with shared pool

Cortona / Montalla

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 200 mi
  • 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 $175 / night

$945 - $1,576 / week

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Responds fast!
avg. 2 hours 33 minutes

from $175 / night

(2) Excellent 

88

Cortona Vacation apartment rental

Province of Arezzo / Cortona

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 18 mi
  • Swimming pool
  • Child friendly
La Fiorita-Farmhouse comprises two separate buildings: the manor house and the outbuilding. The apartment is on the Pink main house and is furnished with a big gazebo for 6 holiday makers. The apartment is tastefully furnished with a typical tuscan kitchen provided with …see more

from $218 / night

$1,522 / week

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from $218 / night

(12) Excellent 

38

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

9 24 3 nights min

  • 9 bedrooms
  • sleeps 24
  • 3 nights min
  • Nearest beach 250 mi
  • 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 $740 / night

$5,176 / week

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from $740 / night

(2) Excellent 

19

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

from $123 / night

$859 - $1,259 / week

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from $123 / night

26

Montalla Vacation farmhouse rental

Cortona / Montalla

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 200 mi
  • Swimming pool
  • Child friendly
I our farm we have a number of houses left intact in theyr original stile. Viila la Bozza is ancient building near a small country village in the country in front of Cortona. Divided in 2 apartments of the same size, completely independent from each other you will have …see more

from $364 / night

$1,928 - $3,423 / week

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Responds fast!
avg. 2 hours 33 minutes

from $364 / 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 $246 / night

$1,717 - $2,861 / week

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from $246 / 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 $70 / night

$485 - $1,288 / week

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from $70 / night

27

Cortona Vacation lodge rental

Province of Arezzo / Cortona

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The "Fattoria Borgonuovo" is located in an agricultural and hilly area of the Val di Chiana, very close to the beautiful and old town of Cortona, and a short distance from the most important historical and wine centers of the southern part of Tuscany, as, Montepulciano, …see more

from $75 / night

$515 - $744 / week

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Responds fast!
avg. 1 hour 19 minutes

from $75 / night

(42) 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 $218 / night

$1,717 - $3,376 / week

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Responds fast!
avg. 58 minutes

from $218 / 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 $171 / night

$1,195 / week

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from $171 / night

47

Vacation villa rental

Province of Arezzo / Cortona

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 145 mi
  • Swimming pool
  • Child friendly
Villa Amelia, now a cosy rental property, was once a small church of the Cortona countryside. San Silvestro church is named in several historical documents, the last one dated 1577 when its control under the territorial cathedral. Later on it was transformed in a clas …see more

from $136 / night

$950 - $1,591 / week

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from $136 / night

(1) Excellent 

24

Vacation villa rental

Province of Arezzo / Cortona

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 60 mi
  • 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 $548 / night

$3,833 - $5,950 / week

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from $548 / night

(2) Excellent 

11

Vacation villa in Cortona

Province of Arezzo / Cortona

4 6 7 nights min

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

from $228 / night

$1,591 - $2,392 / week

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from $228 / night

(1) Excellent 

20

Vacation apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

2 3 min stay varies

  • 2 bedrooms
  • sleeps 3
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • 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 …see more

from $74 / night

$549 - $727 / week

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from $74 / night

(3) Excellent 

80

Vacation townhouse with shared pool in Cortona

Province of Arezzo / Cortona

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Swimming pool
La Fiorita-Farmhouse comprises two separate buildings: the manor house and the outbuilding. The apartment Ortensia is located on the manor house (ground floor) and is furnished with a large gazebo for six persons. The apartment is tastefully furnished with a typical tus …see more

from $218 / night

$1,522 / week

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from $218 / night

(1) Very Good 

27

Lodge rental in Cortona with shared pool

Province of Arezzo / Cortona

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The "Fattoria Borgonuovo" is located in an agricultural and hilly area of the Val di Chiana, very close to the beautiful and old town of Cortona, and a short distance from the most important historical and wine centers of the southern part of Tuscany, as, Montepulciano, …see more

from $90 / night

$626 - $740 / week

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Responds fast!
avg. 1 hour 19 minutes

from $90 / night

(1) Excellent 

36

Vacation villa with swimming pool in Cortona

Province of Arezzo / Cortona

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 19 mi
  • Swimming pool
  • Child friendly
General Description This luxury villa, surrounded by a gorgeous and impressive garden, has been recently restored with great care of details and with respect to Tuscan tradition. What a great location! The villa is ideally located close to village and services offering …see more

from $309 / night

$2,163 / week

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from $309 / night

(26) Excellent 

35

Vacation villa with swimming pool in Cortona

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 $294 / night

$2,060 - $3,318 / week

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from $294 / night

(1) Excellent 

16

Capezzine Vacation apartment rental

Cortona / Capezzine

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Capezzine at Palazzuolo Due is the last restoration we started and will be ready to welcome our Guests next May 2013. It has been declared "Historical Monument" Villa Capezzine is situated in the famous community of Cortona (“Under the Tuscan Sun”: have you seen t …see more

from $138 / night

$973 / week

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from $138 / night

(4) Excellent 

27

Cortona Vacation cottage rental

Province of Arezzo / Cortona

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • 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 $159 / night

$1,114 / week

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Responds fast!
avg. 1 hour 45 minutes

from $159 / night

(1) Excellent 

19

Vacation apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • 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 …see more

from $77 / night

$573 - $763 / week

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from $77 / night

27

Vacation villa rental

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Farm Windmill is located within a private estate of about 8 hectares, planted with olive trees, belonging to Torriti family since 1912. The house with pool is located under the imposing Etruscan walls that surround the town of Cortona, and turning to look a bit 'hig …see more

from $435 / night

$3,044 / week

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from $435 / night

(8) Excellent 

35

Vacation home with shared pool in Montecchio

Cortona / Montecchio

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
…NEW!!! ... .a CORTONA (AR) locations Montecchio, in the countryside and within walking distance to your every wish, it is open to you, a mini releais rich in all comforts to satisfy your every need. Here you will find an intimate, private and welcoming, ready to meet t …see more

from $138 / night

$801 / week

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from $138 / night

(1) Excellent 

16

Cortona Vacation villa accommodation

Province of Arezzo / Cortona

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely small villa is located at 400 m from the charming town of Cortona, one of the most beautiful and renowned towns of Tuscany. An important Etruscan settlement, Cortona today is a medieval jewel on the side of a hill dominating the Val di Chiana. The villa, 65 …see more

from $134 / night

$939 - $1,488 / week

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Responds fast!
avg. 3 hours 5 minutes

from $134 / night

14

Vacation apartment with shared pool in Fratta Santa Caterina

Cortona / Fratta Santa Caterina

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • 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 …see more

from $67 / night

$498 - $638 / week

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from $67 / 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 $91 / night

$630 / week

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from $91 / night

(1) Excellent 

15

Vacation apartment with shared pool in Cortona

Province of Arezzo / Cortona

2 5 5 nights min

  • 2 bedrooms
  • sleeps 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
English: Casa Fiore is an original, hundreds of years old Tuscan house. In former times it belonged to the large country house that is next to it and which nowadays is transformed into a luxurious Bed & Breakfast. The holiday apartment Casa Fiore covers the main house …see more

from $251 / night

$1,752 / week

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from $251 / night

24

Montecchio Vacation villa rental

Cortona / Montecchio

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 155 mi
  • Swimming pool
  • Child friendly
Villa Lo Stagno is a completely independent brickwork farmhouse immersed in the green countryside only few km from the famous town of Cortona. The villa has been recently restored (in June 2017) preserving all its original caracteristics. The villa has been furnished i …see more

from $189 / night

$1,145 - $2,861 / week

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from $189 / night