Cortona Vacation Rentals, Homes, & More

1-50 of 271 Cortona Rentals

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1 / 51

Cortona Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

“ Excellent ”7 Reviews

from

$621

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$621 - $847
Per week:$4,345 - $5,925
Pets allowed:No
Internet:Yes

The best feature of this Cortona villa is, without a doubt, the endless, unobstructed view over the valley below- - literally one of the best panoramas we have ever seen. And the villa itself isn't too shabby, either! With a private swimming pool, comfy living area, and close...

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Cortona Italy Vacation Rentals - Villa
1 / 61

Cortona Villa
6 Bedrooms / 5 Bathrooms / Sleeps 12

from

$191

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$191 - $415
Per week:$1,337 - $2,905
Pets allowed:No
Internet:Yes

Villa Berta is a spacious three- story villa surrounded by the greenery. It sleeps 12 people. From Villa Berta you will have a pleasant view of the Tuscan countryside. Villa Berta is 170 square meters (1830 square feet). It features a private swimming pool, a private garden and winter...

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1 / 8

Cortona Home
2 Bedrooms / 1 Bathroom / Sleeps 4

“ Excellent ”1 Review

from

$98

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$98 - $146
Per week:$685 - $1,016
Pets allowed:Yes
Internet:Yes

Two Bedroom Ground Floor Apartment Cortona Terracotta is a pretty apartment on a lovely estate close to the famous town of Cortona. Furnished in homely Tuscan style the apartment opens directly onto its own garden terrace with table and chairs for dining al fresco. Nearby in the ...

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1 / 14

Cortona Home
6 Bedrooms / 4 Bathrooms / Sleeps 12

from

$180

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$180 - $369
Per week:$1,255 - $2,580
Pets allowed:No
Internet:No

Six Bedroom Detached Villa Cortona Villa Musa is a pretty detached villa in a convenient position just off a local road and within easy reach of the famous town of Cortona. The villa has its own large garden with lawns, and plenty of space for relaxing or dining al fresco, and ...

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1 / 12

Cortona Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$507

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$507 - $743
Per week:$3,547 - $5,198
Pets allowed:No
Internet:Yes

Independent four bedroom villa- Cortona Villa Wind is a fabulous private and newly restored villa, in the midst of the beautiful Tuscan hills, with amazing views and a superb swimming pool. There is ample space for relaxing and eating alfresco, with vineyards and olive groves ...

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1 / 8

Cortona Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$111

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$111 - $158
Per week:$771 - $1,101
Pets allowed:Yes
Internet:Yes

Two Bedroom Ground Floor Apartment Cortona Acquarello is a pretty apartment on a lovely estate close to the famous town of Cortona. Furnished in homely Tuscan style the apartment opens directly onto its own garden terrace with table and chairs for dining al fresco. Nearby in the ...

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1 / 9

Cortona Home
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$149

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$149 - $219
Per week:$1,040 - $1,529
Pets allowed:Yes
Internet:Yes

Independent two bedroom villa- Cortona Cottage Wind O is a fabulous private cottage which lays in the midst of the beautiful Tuscan hills, with amazing views and a superb independent swimming pool. There is ample space for relaxing and eating alfresco, with vineyards and olive ...

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1 / 8

Cortona Home
1 Bedroom / 1 Bathroom / Sleeps 2

from

$74

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$74 - $111
Per week:$514 - $771
Pets allowed:Yes
Internet:Yes

One Bedroom Ground Floor Apartment Cortona Brezza is a pretty apartment on a lovely estate close to the famous town of Cortona. Furnished in homely Tuscan style the apartment opens directly onto its own garden terrace with table and chairs for dining al fresco. Nearby in the lovely...

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1 / 8

Cortona Home
1 Bedroom / 1 Bathroom / Sleeps 2

from

$86

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$86 - $123
Per week:$600 - $857
Pets allowed:Yes
Internet:Yes

One Bedroom Ground Floor Apartment Cortona Focolare is a pretty apartment on a lovely estate close to the famous town of Cortona. Furnished in homely Tuscan style the apartment opens directly onto its own garden terrace with table and chairs for dining al fresco. Nearby in the lovely...

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1 / 9

Cortona Home
1 Bedroom / 1 Bathroom / Sleeps 2

from

$83

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$83 - $174
Per week:$581 - $1,217
Pets allowed:Yes
Internet:Yes

One Bedroom Ground Floor Cottage Southern Tuscany La Chianina is a beautiful detached cottage in a fantastic position with wonderful views of the Chiana valley beyond. It has a lovely garden and a large swimming pool that both also enjoy the pretty panorama. The cottage is furnished...

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1 / 14

Cortona Home
5 Bedrooms / 5 Bathrooms / Sleeps 10

from

$554

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$554 - $733
Per week:$3,877 - $5,125
Pets allowed:Yes
Internet:Yes

Five Bedroom Villa Cortona Set in a beautiful and tranquil position close to the beautiful medieval town of Cortona, Villa Selene is composed of a 19th Century villa and two separate cottages, all beautifully restored and surrounded by extensive grounds with gorgeous gardens and...

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Bedrooms:9
Bathrooms:8
Sleeps:25
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Close to the main house lies a stone independent farmhouse ("Casetto"), recently renovated and equipped with all comforts. It is made up of two independent apartments, each for 4 people. A lovely stone path leads to the loggia, fully equipped for open- air meals. On the ground ...

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Bedrooms:10
Bathrooms:10
Sleeps:20
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The villa is built on three floors. The ground floor hosts two sitting rooms, a dining room with a large wooden table which seats 20, a fully equipped kitchen with dishwasher, one half- bathroom, a cellar and a laundry room. The first floor consists of two spacious double bedrooms,...

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Bedrooms:8
Sleeps:15
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Very close to Cortona ( look up and you will see one of its iconic church domes from nearly every window). You enter the estate by a lovely pebbled drive, and before you are the two buildings that make up this large villa rental in Tuscany. It can be rented for up to 17 people, ...

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Bedrooms:Studio
Sleeps:15
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The accommodation consists of two terracotta- brick farmhouses, not interconnecting with each other, giving the possibility for a large group to holiday together yet retain their own privacy. The new English owner has recently bought and completely restored the original farmhouse...

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Bedrooms:Studio
Bathrooms:1
Sleeps:14
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Set in a large garden, each of the houses has a well- equipped patio for dining outdoors, with stunning views of the surrounding countryside. Large picture windows in the living area of both houses allow one to enjoy the panorama of the rolling Umbrian hills The interiors have been...

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Bedrooms:6
Bathrooms:4
Sleeps:11
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

To provide guests with maximum flexibility in their accommodations, the house has been divided into two independent floors, each with country kitchen opening on to terraces for lounging and outdoor dining. On the upper floor, the house has three double bedrooms and two baths. It...

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1 / 19

Cortona Home
Studio / 3 Bathrooms / Sleeps 9

Bedrooms:Studio
Bathrooms:3
Sleeps:9
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The house which has been divided into two separate floors, each with country kitchen, outdoor eating terrace and living room with open fireplace can sleep up to 9 people. On the ground floor there are two double bedrooms with one bathroom, while on the upper floor there are two...

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1 / 12

Cortona Home
1 Bedroom / 1 Bathroom / Sleeps 8

Bedrooms:1
Bathrooms:1
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

This is a splendid stone farmhouse situated in enchanting hills with extensiveviews of a broad valley and the glorious landscape of Tuscany andUmbria. The fenced garden surrounding the farmhouse and its annex, Capanna, is abundantin olive trees and herb bushes and blends in perfectly...

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Bedrooms:Studio
Bathrooms:2
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Casina Giallo is a charming old house, that has recently been restored, at the top of the Cortona hill commanding a wonderful view. There one can enjoy the changes of season as well as the country life and the rich vegetation of this corner of Tuscany. Casina Giallo is built on ...

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Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

The house has been designed with two bathrooms, country kitchen and living room on each of two floors and provides ample space for eight people, while also offering privacy between floors. Ideal for up to four couples, the house lends itself to a group of friends or inter- generational...

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Bedrooms:6
Bathrooms:1
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

The villa's furnishing combines antiques with comfort and contributes to creating a lovely atmosphere. Main Villa Ground floor: The entrance opens to a reading room and onto a combined living and dining room. This room has a couch, chairs, fireplace, and a table with chairs. The...

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Bedrooms:6
Bathrooms:1
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The Villa has been recently remodelled and equipped with air- conditioning and heating. The interiors are decorated in a Provençal style with soft colors and decorated wood furnishings that will make your holiday comfort unforgettable. The villa is a perfect example of the traditional...

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Bedrooms:Studio
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The house is made up of two floors and can sleep up to 6 people. The ground floor has a spacious sitting room with an open fireplace and a comfortable sofa. The fully equipped kitchen hosts a large dining area. Bathroom and laundry room outdoor. A wooden staircase leads up to the ...

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Bedrooms:Studio
Bathrooms:2
Sleeps:5
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Recently restored old stone Villa of Casona lies up on the hill and is part of a beautiful Renaissance Villa. Located near Cortona, the villa is surrounded by old pine, cypress, lime and oak trees which provide perfect areas for relaxing and reading. The beautiful swimming- pool,...

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Bedrooms:Studio
Bathrooms:1
Sleeps:5
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The villa is built on two floors. Ground floor: comfortably furnished sitting room, fully equipped kitchen, dining room, a double room and a bathroom. A wooden staircase takes you up to the first floor where there is a little kitchen, a double room, a twin bed room and one bathroom....

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Bedrooms:3
Sleeps:3
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Vittorio Sopra is an apartment of 270 sqm in a charming farmhouse ideal for 8 people. The house is furnished according the traditional Tuscan country style: Terracotta tiled floors, exposed wooden beams and hand crafted wrought iron beds. First floor: large kitchen with fireplace,...

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Bedrooms:Studio
Sleeps:2
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Casa Carina, a reconstructed stone barn, which was once a key element in an extended agricultural estate. Recently restored, the house has a dramatic, luminous two- story living room with picture window imbedded in a lovely stone wall, which rises like a natural sculpture on ...

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Bedrooms:Studio
Sleeps:2
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The Relais, with its original conformation, can accomodate up to 35 guests, with 18 rooms of various kinds: Superior, Deluxe, Junior Suite, and Suite. Each room is equipped with every available comfort and is furnished with period furniture: here and there you can find precious...

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Bedrooms:Studio
Sleeps:1
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Tucked in the hills of Cortona, under the ancient Etruscan walls that encircle this beautiful town, lies Casina Rianna, which is surrounded by olive groves, out of which the owners make an excellent extra virgin olive oil which you may taste. Casina Rianna is an old stone house...

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Bedrooms:Studio
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

On the border between Umbria and Tuscany, this lovely restored country house is set on the hillside with lovely views from all rooms. Very private setting. The farmhouse is about 300 square metres (3000 sq ft), surrounded by 6, 5 hectares land, equipped with modern comforts. All...

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Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The Villa consists of 2 floors: on the ground floor a lovely large living/dining room, the small but fully equipped kitchen with wood- burning oven, although small it has everything you need to prepare some wonderful Tuscan meals; There is a dining room and hall. These are 2 large,...

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Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

Tucked in a huge olive grove, chestnut and holm oak wood, the villa offers its guests a breathtaking view over the Valdichiana and the Cortona hills and is the ideal location for those who wish to enjoy total privacy. The ground floor is accessed through the cosy sitting room: here...

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Bedrooms:3
Sleeps:3
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

The property has been lovingly restored using only natural, chemical- free products to preserve the serenity this special place. There is a cork roof, the floors are made of warm Tuscan terracotta and the walls are painted with water colours. Ground floor: There is a sitting room,...

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1 / 48

Cortona Villa
5 Bedrooms / 7 Bathrooms / Sleeps 10

from

$406

/ night

Email Owner
Bedrooms:5
Bathrooms:7
Sleeps:10
Type:Villa
Per night:$406 - $754
Per week:$2,842 - $5,277
Pets allowed:Yes
Internet:Yes

RICEPTIVE STRUCTURE. Nonno Fernando is a farmhouse built entirely in stone whose origins date roughly back to the beginning of the 19th century. In the recent renovation the present owners have preserved the original layout of the various rooms. Salvage materials have been used for...

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1 / 20

Cortona Cottage
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$141

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Cottage
Per night:$141 - $283
Per month:$4,230 - $8,490
Pets allowed:Yes
Internet:No

This romantic cottage with private pool is a very inviting prospect for a holiday in Tuscany. Ideally situated in a peaceful countryside setting, and yet in the heart of Tuscany, Sunflower provides a great base from which you can relax with family, explore Tuscany and visiting ...

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1 / 31
Bedrooms:9
Bathrooms:8
Sleeps:24
Type:Home
Per night:$854 - $1,375
Per week:$5,978 - $9,623
Pets allowed:No
Internet:No

If you’re looking for a rental to accommodate a group of couples with children in a fun and rustic environment you’ve come to the right place! Located just outside of hilltop town of Cortona this medieval stone hamlet is comprised of seven units in a quiet setting surrounded ...

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1 / 45

Cortona Home
10 Bedrooms / 7 Bathrooms / Sleeps 20

from

$980

/ night

Email Owner
Bedrooms:10
Bathrooms:7
Sleeps:20
Type:Home
Per night:$980
Per month:$29,400
Pets allowed:No
Internet:No

Nature, culture, history and traditions meet in this splendid villa in Cortona, in the Tuscan region. Large and with an adjacent cottage for two, this villa is perfect for big groups. Additional amenities include: pets considered, heating....

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1 / 37

Cortona Home
3 Bedrooms / 5 Bathrooms / Sleeps 10

from

$382

/ night

Email Owner
Bedrooms:3
Bathrooms:5
Sleeps:10
Type:Home
Per night:$382 - $611
Per week:$2,671 - $4,277
Pets allowed:No
Internet:No

This cozy villa in Cortona can accommodate up to 6 people. It has a swimming pool, a living room, 5 bedrooms and 5 bathrooms. Additional amenities include: pets considered, heating....

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1 / 20

Cortona Villa
5 Bedrooms / 5 Bathrooms / Sleeps 10

from

$485

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Villa
Per night:$485 - $904
Per week:$3,390 - $6,327
Pets allowed:No
Internet:Yes

A group of ten will surely have a delightful time while they explore the gorgeous Valdichiana and stay at this villa rental. Dating back to the 16th century, this vacation rental is surrounded by extensive grounds with a swimming pool and incredible views. Plus, the hilltop town...

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1 / 14

Cortona Home
4 Bedrooms / 4 Bathrooms / Sleeps 9

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:9
Type:Home
Per night:$358 - $474
Per month:$10,740 - $14,220
Pets allowed:No
Internet:No

This secluded Tuscan villa sleeps up to 8 people and it offers stunning views of the valley. Cozy atmosphere inside and a beautiful garden with swimming pool outside, the house is perfect for a tranquil experience in Tuscany. Additional amenities include: heating....

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Cortona Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$485

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$485 - $872
Per week:$3,390 - $6,099
Pets allowed:No
Internet:Yes

You will feel like you’re in a storybook once you step foot along the path that leads to this villa. Flowers, trees, and plants abound on the extensive grounds of this property. Complete with a pool and lovely terrace, this villa near Cortona is a gem. (11 hectares)This villa...

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1 / 19

Cortona Home
2 Bedrooms / 3 Bathrooms / Sleeps 8

from

$322

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:8
Type:Home
Per night:$322 - $358
Per month:$9,660 - $10,740
Pets allowed:No
Internet:No

A classic Tuscan villa for 6 in the heart of the Valdichiana near Cortona and Arezzo it is ideally located for exploring the region but also has all you could want for lazy holiday days relaxing on site by the private pool. Additional amenities include: heating....

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1 / 18

Cortona Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$230

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$230 - $367
Per week:$1,607 - $2,565
Pets allowed:No
Internet:No

With its own private garden, this lovely two- storey villa offers its guests comfortable and fantastic accommodation in the Tuscan countryside. Additional amenities include: heating....

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1 / 37

Cortona Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$516

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$516 - $676
Per week:$3,611 - $4,732
Pets allowed:No
Internet:No

Located in Cortona, this fabulous villa offers a fabulous swimming pool, a fully equipped kitchen and a special surprise in each room to help guests relax and enjoy the best of holidays. Additional amenities include: heating....

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1 / 21

Cortona Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$374

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$374 - $522
Per month:$11,220 - $15,660
Pets allowed:No
Internet:No

With its stone walls, fabulous swimming pool and comfortable and luxurious common areas, this villa for 8 offers guests everything they need in a secluded spot right outside the center of Cortona. Additional amenities include: heating....

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Cortona Italy Vacation Rentals - Home
1 / 36

Cortona Home
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$446

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
Per night:$446 - $505
Per month:$13,380 - $15,150
Pets allowed:No
Internet:No

With a private swimming pool and spectacular views of the valley, this villa accommodates up to 8 people and it offers all comforts anyone would need for the perfect vacation in Tuscany. Additional amenities include: heating....

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Cortona Italy Vacation Rentals - Apartment
1 / 35

Cortona Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$362

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$362
Per week:$2,528
Pets allowed:No
Internet:Yes

Is this an apartment or a hotel room? In fact, it combines the best of both worlds: the privacy and spaciousness of your own large Tuscany apartment, along with a restaurant on- site and full time staff eager to help you with any difficulties that may arise—or simply to recommend...

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Cortona Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$178

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$178 - $255
Per week:$1,246 - $1,781
Pets allowed:No
Internet:No

This villa mixes the unique Tuscan style with elegant and modern comforts, and it is the perfect getaway for a family. It affords its own kitchen, 2 bedrooms and 2 bathrooms and a garden with swimming pool, BBQ area and spectacular views. Additional amenities include: heating....

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Cortona Home
3 Bedrooms / 4 Bathrooms / Sleeps 6

from

$446

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$446
Per month:$13,380
Pets allowed:No
Internet:No

This enchanting villa placed between Castiglion Fiorentino and Cortona can accommodate up to 6 people and is a wonderful place to stay if you and your group are looking for private and relaxing holiday in Tuscany. Additional amenities include: heating....

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