Cortona Vacation Rentals, Villas, & More

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Cortona Italy Vacation Rentals - Apartment
1 / 20

Cortona Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 42 BR / 2 BA / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$195

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$195 - $249
Per month:$5,850 - $7,470
Pets allowed:No
Internet:No

At the foot of the hills upon which Cortona, the Etruscan city par excellance, rises, is this ancient country house, a splendid Medicean construction finely restored and transformed into 13 flats, 4 of which are holiday flats and the others are, more or less, lived in occasionally....

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Cortona Italy Vacation Rentals - Apartment
1 / 21

Cortona Apartment
2 Bedrooms / 1 Bathroom / Sleeps 42 BR / 1 BA / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$122

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$122 - $179
Per month:$3,660 - $5,370
Pets allowed:No
Internet:Yes

SOFIA - Romantic Modern Charm in the Heart of Cortona This beautiful penthouse apartment of approximately 55 m2 (600 sq. ft. ) has classic Italian beamed ceilings, a wood burning fireplace for cozy winter nights, and unforgettable Tuscan views that everyone dreams of. The...

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1 / 23

Cortona Villa
14 Bedrooms / 9 Bathrooms / Sleeps 3014 BR / 9 BA / Sleeps 30
Villa / 14 Bedrooms / Sleeps 30
(1) Excellent 1 Review

from

$525

/ night

Email Owner
Bedrooms:14
Bathrooms:9
Sleeps:30
Type:Villa
Per night:$525 - $1,194
Per week:$3,670 - $8,357
Pets allowed:Yes
Internet:Yes

This exclusive villa that dominates a huge landed property offers magnificent views of the surrounding countryside, and is situated on the gentle rolling hills of the Tuscan/Umbrian border between Montepulciano, Cortona and Lake Trasimeno. This is a central location of southern ...

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Cortona Italy Vacation Rentals - Villa
1 / 68

Cortona Villa
13 Bedrooms / 13 Bathrooms / Sleeps 2613 BR / 13 BA / Sleeps 26
Villa / 13 Bedrooms / Sleeps 26

from

$707

/ night

Email Owner
Bedrooms:13
Bathrooms:13
Sleeps:26
Type:Villa
Per night:$707 - $1,223
Per week:$4,945 - $8,559
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. An imposing manor house and two outbuildings, an old tobacco drying kiln and the old oven where all the sharcropper families once went to bake their bread, constitute Le Caselle, a property that recent renovations (the last one in 2014) have transformed from...

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Cortona Italy Vacation Rentals - Villa
1 / 60

Cortona Villa
9 Bedrooms / 11 Bathrooms / Sleeps 229 BR / 11 BA / Sleeps 22
Villa / 9 Bedrooms / Sleeps 22
(1) Excellent 1 Review

from

$521

/ night

Email Owner
Bedrooms:9
Bathrooms:11
Sleeps:22
Type:Villa
Per night:$521 - $886
Per week:$3,647 - $6,200
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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Cortona Italy Vacation Rentals - Villa
1 / 71

Cortona Villa
9 Bedrooms / 7 Bathrooms / Sleeps 209 BR / 7 BA / Sleeps 20
Villa / 9 Bedrooms / Sleeps 20

from

$525

/ night

Email Owner
Bedrooms:9
Bathrooms:7
Sleeps:20
Type:Villa
Per night:$525 - $753
Per week:$3,673 - $5,268
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. An eighteenth century structure only a few kilometers away from Lake Trasimeno with the Etruscan town of Cortona behind it, Villa delle Sophore stands on what was once the border between the Grand Duchy of Tuscany and the Papal States and a smuggling area. The...

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Cortona Italy Vacation Rentals - Villa
1 / 60

Cortona Villa
10 Bedrooms / 9 Bathrooms / Sleeps 2010 BR / 9 BA / Sleeps 20
Villa / 10 Bedrooms / Sleeps 20

from

$544

/ night

Email Owner
Bedrooms:10
Bathrooms:9
Sleeps:20
Type:Villa
Per night:$544 - $951
Per week:$3,804 - $6,657
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. Le Caselle is an imposing manor house that recent renovations (the last one in 2014) have transformed from farmhouse to dream house. In the elegant rooms are many traditional elements - terracotta, stone, rustic fireplace, vaulted ceilings - but just as many...

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1 / 27

Cortona Villa
10 Bedrooms / 10 Bathrooms / Sleeps 2010 BR / 10 BA / Sleeps 20
Villa / 10 Bedrooms / Sleeps 20
(7) Excellent 7 Reviews
Bedrooms:10
Bathrooms:10
Sleeps:20
Type:Villa
Per night:$2,045 - $3,515
Per week:$14,315 - $24,605
Pets allowed:No
Internet:Yes

A stay at Villa Laura is your chance to live out your own Under the Tuscan Sun. This ten- bedroom property played the role of the villa Bramasole in the film. Just as the fictional villa is given a makeover, Villa Laura was recently renovated with an eye to traditional style and ...

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1 / 75

Cortona Villa
8 Bedrooms / 9 Bathrooms / Sleeps 178 BR / 9 BA / Sleeps 17
Villa / 8 Bedrooms / Sleeps 17

from

$598

/ night

Email Owner
Bedrooms:8
Bathrooms:9
Sleeps:17
Type:Villa
Per night:$598 - $1,087
Per week:$4,184 - $7,608
Pets allowed:Yes
Internet:Yes

Receptive Structure. La Madonnina is a beautiful property, with a main building and two annexes built entirely in stone, which owes its name to the discovery, during renovation work, inside one of the chimney flues of a bas- relief depicting the Madonna and Child which has been...

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1 / 26

Cortona Villa
7 Bedrooms / 5 Bathrooms / Sleeps 157 BR / 5 BA / Sleeps 15
Villa / 7 Bedrooms / Sleeps 15
(1) Excellent 1 Review

from

$430

/ night

Email Owner
Bedrooms:7
Bathrooms:5
Sleeps:15
Type:Villa
Per night:$430 - $796
Per week:$3,010 - $5,572
Pets allowed:No
Internet:Yes

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 at the same time absolute privacy...

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Cortona Italy Vacation Rentals - Villa
1 / 73

Cortona Villa
7 Bedrooms / 12 Bathrooms / Sleeps 147 BR / 12 BA / Sleeps 14
Villa / 7 Bedrooms / Sleeps 14
(1) Excellent 1 Review

from

$656

/ night

Email Owner
Bedrooms:7
Bathrooms:12
Sleeps:14
Type:Villa
Per night:$656 - $1,045
Per week:$4,586 - $7,311
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. Casale dei Girasoli stands on a hill surrounded by the splendid Tuscan countryside stretching from Cortona to Sinalunga and from Arezzo to Montepulciano. A location immersed in nature, ideal for those seeking a peaceful holiday. The pre- existing farmhouse, built...

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Cortona Italy Vacation Rentals - Villa
1 / 52

Cortona Villa
7 Bedrooms / 9 Bathrooms / Sleeps 147 BR / 9 BA / Sleeps 14
Villa / 7 Bedrooms / Sleeps 14

from

$417

/ night

Email Owner
Bedrooms:7
Bathrooms:9
Sleeps:14
Type:Villa
Per night:$417 - $730
Per week:$2,918 - $5,106
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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Cortona Italy Vacation Rentals - Villa
1 / 56

Cortona Villa
7 Bedrooms / 9 Bathrooms / Sleeps 147 BR / 9 BA / Sleeps 14
Villa / 7 Bedrooms / Sleeps 14

from

$490

/ night

Email Owner
Bedrooms:7
Bathrooms:9
Sleeps:14
Type:Villa
Per night:$490 - $951
Per week:$3,424 - $6,657
Pets allowed:Yes
Internet:Yes

STRUCTURE RECEPTIVE. Le Caselle is an imposing manor house that recent renovations (the last one in 2014) have transformed from farmhouse to dream house. In the elegant rooms are many traditional elements - terracotta, stone, rustic fireplace, vaulted ceilings - but just as many...

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Cortona Italy Vacation Rentals - Villa
1 / 70

Cortona Villa
6 Bedrooms / 8 Bathrooms / Sleeps 146 BR / 8 BA / Sleeps 14
Villa / 6 Bedrooms / Sleeps 14

from

$544

/ night

Email Owner
Bedrooms:6
Bathrooms:8
Sleeps:14
Type:Villa
Per night:$544 - $951
Per week:$3,804 - $6,657
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. La Madonnina is a beautiful property, with a main building and an annex built entirely in stone, which owes its name to the discovery, during renovation work, inside one of the chimney flues of a bas- relief depicting the Madonna and Child which has been preserved...

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1 / 33

Cortona Villa
6 Bedrooms / 5 Bathrooms / Sleeps 126 BR / 5 BA / Sleeps 12
Villa / 6 Bedrooms / Sleeps 12
(7) Excellent 7 Reviews

from

$889

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$889 - $1,157
Per week:$6,222 - $8,098
Pets allowed:No
Internet:Yes

What a great holiday villa in Tuscany this is for a group of friends who love scenic walks and the ability to walk right into the town of Cortona! When you and your large group of family and friends want a firsthand look at Tuscany, try taking a leisurely stroll away from this villa...

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1 / 13

Cortona Home
6 Bedrooms / 4 Bathrooms / Sleeps 126 BR / 4 BA / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

from

$164

/ night

Email Owner
Bedrooms:6
Bathrooms:4
Sleeps:12
Type:Home
Per night:$164 - $338
Per week:$1,148 - $2,360
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 / 36

Cortona Villa
5 Bedrooms / 7 Bathrooms / Sleeps 125 BR / 7 BA / Sleeps 12
Villa / 5 Bedrooms / Sleeps 12

from

$273

/ night

Email Owner
Bedrooms:5
Bathrooms:7
Sleeps:12
Type:Villa
Per night:$273 - $528
Per week:$1,911 - $3,692
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. With a 180° view of the Carpina Valley - an area set between the Upper Tiber Valley and the Umbria- Marche Apennine ridge where the Carpina river and its tributaries determine the succession of hills with alternating dense oak forests, vineyards and olive groves...

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1 / 40

Cortona Villa
5 Bedrooms / 4 Bathrooms / Sleeps 125 BR / 4 BA / Sleeps 12
Villa / 5 Bedrooms / Sleeps 12
(3) Excellent 3 Reviews

from

$337

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:12
Type:Villa
Per night:$337 - $570
Per week:$2,356 - $3,988
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. A stone parlour, where art and nature unite to form a perfect partnership: Cortona is a magical place with a timeless charm that envelops the visitor with its vibrant atmosphere, suspended between the history and legend of its origins, surprising him each time,...

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Cortona Italy Vacation Rentals - Villa
1 / 44

Cortona Villa
4 Bedrooms / 5 Bathrooms / Sleeps 124 BR / 5 BA / Sleeps 12
Villa / 4 Bedrooms / Sleeps 12

from

$225

/ night

Email Owner
Bedrooms:4
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$225 - $494
Per week:$1,570 - $3,453
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. A scenic avenue lined with cypress trees – this is the first thing seen by the guests of this beautiful property located in the Val Tiberina, an uncontaminated area of Umbria on the border with Tuscany. Il Cerreto is the old tobacco kiln of a large property dating...

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Cortona Italy Vacation Rentals - Villa
1 / 64

Cortona Villa
7 Bedrooms / 5 Bathrooms / Sleeps 127 BR / 5 BA / Sleeps 12
Villa / 7 Bedrooms / Sleeps 12

from

$380

/ night

Email Owner
Bedrooms:7
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$380 - $587
Per week:$2,659 - $4,108
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. An eighteenth century structure only a few kilometers away from Lake Trasimeno with the Etruscan town of Cortona behind it, Villa delle Sophore stands on what was once the border between the Grand Duchy of Tuscany and the Papal States and a smuggling area. The...

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Cortona Italy Vacation Rentals - Villa
1 / 44

Cortona Villa
6 Bedrooms / 5 Bathrooms / Sleeps 126 BR / 5 BA / Sleeps 12
Villa / 6 Bedrooms / Sleeps 12

from

$408

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$408 - $653
Per week:$2,853 - $4,565
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. Poggio Sorbello is a typical farmhouse in open- face stone, warm and welcoming. The oldest part dates back to the early 20th century when it was nothing more than a simple barn; it has retained the original materials with the beautiful terracotta floors and wooden-...

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Cortona Italy Vacation Rentals - Home
1 / 17

Cortona Home
5 Bedrooms / 5 Bathrooms / Sleeps 125 BR / 5 BA / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$536

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:12
Type:Home
Per night:$536 - $832
Per week:$3,748 - $5,818
Pets allowed:No
Internet:Yes

Independent five bedroom villa- Cortona Villa Wind is a fabulous private villa, with a separate Cottage, Wind O just below it. It is a 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...

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1 / 34

Cortona Home
4 Bedrooms / 6 Bathrooms / Sleeps 114 BR / 6 BA / Sleeps 11
Home / 4 Bedrooms / Sleeps 11
(3) Excellent 3 Reviews

from

$426

/ night

Email Owner
Bedrooms:4
Bathrooms:6
Sleeps:11
Type:Home
Per night:$426 - $802
Per week:$2,982 - $5,612
Pets allowed:No
Internet:Yes

Bring a group of friends and stay in this Tuscany vacation rental! A food shop, tabacchi, pharmacy and butcher shop are less than one km from this Tuscany villa, so you can purchase groceries to make dinner and eat al fresco on your own private patio. Relax on the large estate...

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1 / 15

Cortona Home
5 Bedrooms / 4 Bathrooms / Sleeps 105 BR / 4 BA / Sleeps 10
Home / 5 Bedrooms / Sleeps 10
(11) Excellent 11 Reviews

from

$261

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
Per night:$261 - $510
Per week:$1,823 - $3,569
Pets allowed:Yes
Internet:Yes

This secluded haven is a wonderful destination if you’re looking to celebrate a family reunion or gathering. It’s located on a large estate with a private swimming pool, garden, and panoramic views of the Chiana Valley and Tuscan landscape. This holiday accommodation is comprised...

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1 / 13

Cortona Home
5 Bedrooms / 5 Bathrooms / Sleeps 105 BR / 5 BA / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

from

$507

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$507 - $601
Per week:$3,547 - $4,207
Pets allowed:No
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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1 / 24

Cortona Villa
5 Bedrooms / 4 Bathrooms / Sleeps 105 BR / 4 BA / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$391

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Villa
Per night:$391
Per month:$11,730
Pets allowed:Yes
Internet:Yes

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. Modern ...

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1 / 20

Cortona Villa
5 Bedrooms / 4 Bathrooms / Sleeps 105 BR / 4 BA / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$401

/ night

Email Owner
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Villa
Per night:$401
Per month:$12,030
Pets allowed:Yes
Internet:Yes

Extending over the ground and top floors of part of a large villa, this superior accommodation provides more than just a touch of distinctive style and class! It comprises all modern comforts, while retaining many original Tuscan design features and elegant traditional furnishings....

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Cortona Italy Vacation Rentals - Villa
1 / 61

Cortona Villa
5 Bedrooms / 10 Bathrooms / Sleeps 105 BR / 10 BA / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10
(2) Very Good 2 Reviews

from

$554

/ night

Email Owner
Bedrooms:5
Bathrooms:10
Sleeps:10
Type:Villa
Per night:$554 - $836
Per week:$3,877 - $5,851
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. Casale dei Girasoli stands on a hill surrounded by the splendid Tuscan countryside stretching from Cortona to Sinalunga and from Arezzo to Montepulciano. A location immersed in nature, ideal for those seeking a peaceful holiday. The pre- existing farmhouse, built...

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Cortona Italy Vacation Rentals - Villa
1 / 36

Cortona Villa
5 Bedrooms / 5 Bathrooms / Sleeps 105 BR / 5 BA / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$253

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Villa
Per night:$253 - $607
Per week:$1,766 - $4,244
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. Torretta is a splendid antique property, located on the top of a nice hill next to the Medieval town of Cortona. Being surrounded by oak- trees and olive- trees, you can appreciate the Tuscan country side. What makes the property unique is, on one side, it's...

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Cortona Italy Vacation Rentals - Villa
1 / 48

Cortona Villa
5 Bedrooms / 7 Bathrooms / Sleeps 105 BR / 7 BA / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$365

/ night

Email Owner
Bedrooms:5
Bathrooms:7
Sleeps:10
Type:Villa
Per night:$365 - $678
Per week:$2,553 - $4,742
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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Cortona Italy Vacation Rentals - Villa
1 / 23

Cortona Villa
5 Bedrooms / 5 Bathrooms / Sleeps 105 BR / 5 BA / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$429

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Villa
Per night:$429 - $801
Per week:$3,003 - $5,606
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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Cortona Italy Vacation Rentals - Villa
1 / 35

Cortona Villa
5 Bedrooms / 5 Bathrooms / Sleeps 105 BR / 5 BA / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$314

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Villa
Per night:$314 - $595
Per week:$2,193 - $4,159
Pets allowed:No
Internet:Yes

Large renovated house situated next to the owners' villa in the hills just outside the ancient Etruscan city of Cortona, famous for the remains of this ancient civilization. The walls that surround the city and the old streets of the city make it a place with particular charm: antique...

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1 / 30

Cortona Villa
5 Bedrooms / 5 Bathrooms / Sleeps 95 BR / 5 BA / Sleeps 9
Villa / 5 Bedrooms / Sleeps 9
(2) Excellent 2 Reviews

from

$429

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:9
Type:Villa
Per night:$429 - $772
Per week:$3,003 - $5,404
Pets allowed:No
Internet:Yes

Directly overlooking the Valdichiana and olive groves, this holiday villa is truly in a peaceful setting. Located just five kilometers from Cortona, this villa features a large terrace that is perfect for outdoor dining and relaxing. For a quiet and serene visit with family or friends...

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Cortona Italy Vacation Rentals - Villa
1 / 32

Cortona Villa
5 Bedrooms / 3 Bathrooms / Sleeps 95 BR / 3 BA / Sleeps 9
Villa / 5 Bedrooms / Sleeps 9

from

$317

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:9
Type:Villa
Per night:$317 - $476
Per week:$2,216 - $3,332
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. La Giurata is a typical country farmhouse immersed in the green with an exceptional view over the hills of Umbria and Tuscany, famous for their beauty and charm. This house is recommended for those who love direct contact with nature and the tranquillity of the...

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Cortona Italy Vacation Rentals - Home
1 / 19

Cortona Home
3 Bedrooms / 2 Bathrooms / Sleeps 93 BR / 2 BA / Sleeps 9
Home / 3 Bedrooms / Sleeps 9

from

$153

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:9
Type:Home
Per night:$153 - $373
Per week:$1,070 - $2,609
Pets allowed:No
Internet:No

Dardano is a simple but charming 3 bedroom farmhouse sleeping up to 9 people. Outside guests enjoy a private garden and private swimming pool (open from mid May to the end of September each year). Inside it is furnished simply but tastefully in a traditional Tuscan style. The farmhouse...

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1 / 24

Cortona Apartment
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Apartment / 4 Bedrooms / Sleeps 8
(1) Excellent 1 Review

from

$507

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Apartment
Per night:$507
Per week:$3,547
Pets allowed:No
Internet:Yes

Have your own “Under the Tuscan Sun” experience in this historic apartment in Cortona, a small and picturesque hilltop town in Tuscany. Narrow winding lanes lead you to original little shops, piazzas with cafes, good restaurants, and living history. From your rooftop terrace...

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Cortona Italy Vacation Rentals - Villa
1 / 39

Cortona Villa
4 Bedrooms / 4 Bathrooms / Sleeps 84 BR / 4 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8
(2) Excellent 2 Reviews

from

$429

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$429 - $772
Per week:$3,003 - $5,404
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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Cortona Italy Vacation Rentals - Home
1 / 11

Cortona Home
4 Bedrooms / 4 Bathrooms / Sleeps 84 BR / 4 BA / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$16

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$16 - $680
Per week:$112 - $4,755
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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Cortona Italy Vacation Rentals - Villa
1 / 36

Cortona Villa
3 Bedrooms / 2 Bathrooms / Sleeps 83 BR / 2 BA / Sleeps 8
Villa / 3 Bedrooms / Sleeps 8

from

$293

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Villa
Per night:$293 - $505
Per week:$2,047 - $3,531
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. Bellora is a charming little brick property which is situated in the beautiful Tuscan countryside between Cortona and Montepulciano, close to the natural oasis of the lake of Montepulciano. Internally the property has been finished with “cotto” flooring, wooden...

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Cortona Italy Vacation Rentals - Villa
1 / 40

Cortona Villa
4 Bedrooms / 4 Bathrooms / Sleeps 84 BR / 4 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8
(2) Excellent 2 Reviews

from

$269

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$269 - $427
Per week:$1,883 - $2,985
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. Casale Cinque Valli is immersed in the beautiful Tuscany landscape near Cortona, delightful medieval town at the Tuscan- Umbria border. Thanks to its breathtaking landscape this house is the ideal place for those who want to enjoy the silence and nature. Internally...

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Cortona Italy Vacation Rentals - Villa
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Cortona Villa
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$304

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$304 - $475
Per week:$2,124 - $3,323
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE Casale Lamate is a house which, although of recent construction, has retained the unique charm of the Tuscan farmhouses thanks to the recycling and use of materials originating in these areas, such as the handmade terracotta floors and the beautiful chestnut ceiling...

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Cortona Italy Vacation Rentals - Villa
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Cortona Villa
5 Bedrooms / 3 Bathrooms / Sleeps 85 BR / 3 BA / Sleeps 8
Villa / 5 Bedrooms / Sleeps 8

from

$196

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$196 - $408
Per week:$1,370 - $2,853
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. I Mandorli is a typical Tuscan stone farmhouse, located a few kilometres from Cortona, a charming little town in the heart of Tuscany. The property is part of a farm estate of about 6 hectares where the owners produce olive oil and wine which they share with...

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Cortona Italy Vacation Rentals - Villa
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Cortona Villa
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8
(1) Excellent 1 Review

from

$240

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$240 - $425
Per week:$1,679 - $2,973
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. Casale la Contea, located high on the slopes of a gentle rolling hill, is a stone building provided with beautiful porch's on two sides of this splendid property. Guests can enjoy a panoramic view of the Trasimeno Lake and the picturesque Tuscan- Umbrian countryside....

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Cortona Italy Vacation Rentals - Villa
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Cortona Villa
3 Bedrooms / 3 Bathrooms / Sleeps 83 BR / 3 BA / Sleeps 8
Villa / 3 Bedrooms / Sleeps 8

from

$221

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$221 - $440
Per week:$1,543 - $3,079
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. Villa Fabi is a delightful little farmhouse built entirely of local stone and situated in the beautiful Tuscan countryside not far from Cortona. The interior has terracotta tiled floors and tiled ceilings with exposed beams. The house is simply furnished but with...

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Cortona Italy Vacation Rentals - Villa
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Cortona Villa
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$279

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$279 - $595
Per week:$1,950 - $4,159
Pets allowed:No
Internet:Yes

Ancient stone- built farmhouse near Cortona that has been renovated and transformed into a delightful villa. Inside a property which includes Villa Orlando and Liliana, situated on the side of a hill covered with olive trees and small wood groves just outside of Cortona, an ancient...

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Cortona Italy Vacation Rentals - Home
1 / 21

Cortona Home
4 Bedrooms / 4 Bathrooms / Sleeps 84 BR / 4 BA / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$296

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$296 - $595
Per week:$2,068 - $4,159
Pets allowed:No
Internet:Yes

Beautiful renovated house situated in the hills just outside of Cortona, an Etruscan city par excellence, where you can still see its powerful city walls. The house is located on a hillside covered with olive trees rising above the Chiana valley and granting a beautiful panorama....

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Cortona Italy Vacation Rentals - Villa
1 / 28

Cortona Villa
4 Bedrooms / 5 Bathrooms / Sleeps 84 BR / 5 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$238

/ night

Email Owner
Bedrooms:4
Bathrooms:5
Sleeps:8
Type:Villa
Per night:$238 - $422
Per week:$1,662 - $2,954
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. With a 180° view of the Carpina Valley - an area set between the Upper Tiber Valley and the Umbria- Marche Apennine ridge where the Carpina river and its tributaries determine the succession of hills with alternating dense oak forests, vineyards and olive groves...

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Cortona Italy Vacation Rentals - Villa
1 / 48

Cortona Villa
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$293

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$293 - $571
Per week:$2,047 - $3,994
Pets allowed:Yes
Internet:Yes

RECEPTIVE STRUCTURE. Albachiara stands in the sweet, green Val di Chiana between Siena and Arezzo and just minutes away from fascinating Cortona, one of the oldest Etruscan towns in Tuscany on a hill 600 m above sea level. An attractive stone farmhouse, it was originally a farm...

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Cortona Italy Vacation Rentals - Villa
1 / 48

Cortona Villa
4 Bedrooms / 3 Bathrooms / Sleeps 84 BR / 3 BA / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$245

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$245 - $490
Per week:$1,712 - $3,424
Pets allowed:Yes
Internet:Yes

PRIVATE STRUCTURE. The beautiful land on which Villa Vagnucci lies, below Cortona and immersed in the lush garden of the Valdichiana, extends between the provinces of Siena and Arezzo, on the border between Tuscany and Umbria. The villa was originally a manor house, with the central...

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Cortona Italy Vacation Rentals - Villa
1 / 31

Cortona Villa
3 Bedrooms / 4 Bathrooms / Sleeps 83 BR / 4 BA / Sleeps 8
Villa / 3 Bedrooms / Sleeps 8
(1) Excellent 1 Review

from

$935

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$935 - $1,142
Per week:$6,545 - $7,994
Pets allowed:No
Internet:Yes

In the 18th century, Villa Tegognano was a country retreat for an aristocratic family. Today, this renovated four- bedroom manor house is still a quiet getaway, but with modern amenities. With commanding views of the countryside near Cortona, the villa’s location is unforgettable,...

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