Cortona Villas, Holiday rentals and apartments

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona

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  • Bagnolo (3)
  • Cantalena (1)
  • Capezzine (3)
  • Cegliolo (5)
  • Centoia (8)
  • Farinaio (5)
  • Fratta Santa Caterina (10)
  • Fratticciola (12)
  • Localita Mucchia (2)
  • Mercatale (7)
  • Mercatale di Cortona (17)
  • Montalla (16)
  • Montanare (10)
  • Montecchio (17)
  • Montecchio, San Lorenzo (2)
  • Pietraia (8)
  • Poggioni (4)
  • Ruffignano (1)
  • Teverina (6)

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714 Holiday homes

Travellers going to Cortona are booking August dates now. Secure your holiday home today and have the perfect trip.

1 / 31

Il Castagno, splendid tuscan villa among vineyards

Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
Villa Il Castagno is the heart of the wine estate of the same name, which is located in enchanting hilly position among vineyards and olive groves and from which one can catch sights of the evoking shape of the near town of Cortona. Guests will have the chance to stay i  …see more

from £342 / night

£2375 - £3750 / week

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from £342 / night

(1) Excellent 

1 / 19

La Pergola, Romantic Villa with Very Nice Loggia

Province of Arezzo / Cortona

5 bedroomsSleeps 87 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £179 / night

£1250 - £2625 / week

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from £179 / night

(2) Very Good 

1 / 24

Idyllic Tuscan villa with annexes, outdoor pool an

Province of Arezzo / Cortona

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 140 km; Swimming pool; Great for children of all ages ;
Villa Le Contesse sleeps 6+2 people in three bedrooms with three bathrooms and another four people in two annexes (Serenella & Limonaia), each with it's own living room, kitchenette bathroom and bedroom. It nestles in the immediate out skirts of Cortona, one of the many  …see more

from £225 / night

£1575 - £1909 / week

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from £225 / night

1 / 18

Tuscany traditional 3 bedroom farmhouse - Cortona farmhouse sleeps 9

Province of Arezzo / Cortona

3 bedroomsSleeps 97 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
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. It is  …see more

from £157 / night

£1095 - £1595 / week

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from £157 / night

1 / 19

Agriturismo Poggio del Fabbro - Poggioni villa sleeps 7

Cortona / Poggioni

4 bedroomsSleeps 7Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
L'agriturismo Poggio del Fabbro è situato in località San Pietro a Dame, frazione del comune di Cortona nella montagna cortonese, a 20km dalla città, in una posizione tranquilla e isolata tra le verdi montagne ad un'altezza di 700m slm al confine tra Toscana e Umbria  …see more

from £108 / night

£0 / week

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from £108 / night

(5) Excellent 

1 / 20

Province of Arezzo / Cortona

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car advised;
 …see more

from £42 / night

£250 - £400 / week

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from £42 / night

(2) Very Good 

1 / 24

Fattoria Borgonuovo - Geranio - Cortona lodge sleeps 4

Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
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, Mont  …see more

from £55 / night

£375 - £575 / week

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from £55 / night

(4) Excellent 

1 / 30

Villa le Celle del Farinaio: Tuscan home with stunning valley views, swimming pool and trampoline, sleeps fourteen

Cortona / Farinaio

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car advised;
The cells of the villa Farinaio is situated in a beautiful hilly which overlooks the valley below and it is surrounded by green woods of our own property where you can find numerous hiking trails with different difficulty levels for taking a walk. The villa is completel  …see more

from £179 / night

£1250 - £2500 / week

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from £179 / night

1 / 13

Cortona / Montecchio

4 bedroomsSleeps 11Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Great for children of all ages ; Pets welcome;
 …see more

from £125 / night

£874 - £1530 / week

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from £125 / night

(2) Excellent 

1 / 23

Tuscan holiday farmhouse villa features stunning grounds and pool, sleeps 4

Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £100 / night

£667 - £750 / week

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from £100 / night

1 / 19

Province of Arezzo / Cortona

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £55 / night

£238 - £367 / week

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from £55 / night

(1) Excellent 

1 / 24

Il Moro Novo - Montalla apartment sleeps 3

Cortona / Montalla

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 i  …see more

from £59 / night

£306 - £597 / week

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from £59 / night

1 / 100

Nina - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Great for children of all ages ;
ExteriorsThis beautiful and secluded villa lies in Cortona's countryside, with spectacular views over the valley, Cortona and Trasimeno Lake. Located only a couple of minutes from the town center, it is also very close to the most famous art cities in the world, wh  …see more

from £215 / night

£1500 / week

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from £215 / night

(1) Excellent 

1 / 24

Stunning Tuscan villa with five bedrooms, private

Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 125 km; Swimming pool; Great for children of all ages ;
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 £124 / night

£863 - £2125 / week

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from £124 / night

(1) Excellent 

1 / 79

Province of Arezzo / Cortona

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 16 km; Swimming pool;
 …see more

from £101 / night

£673 - £841 / week

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from £101 / night

1 / 12

Villa Cuiano- La Stalla - Mercatale di Cortona apartment sleeps 4

Cortona / Mercatale di Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 12 km; Swimming pool; Great for children of all ages ;
If you take the road which follows the Tuscan-Umbrian border you come to Pierle, a medieval hamlet in the hills between Cortona and Lake Trasimeno, its castle dominating the verdant valley below.Here surrounded by olive groves and woodland of oaks and chestnuts, you wil  …see more

from £84 / night

£500 - £750 / week

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from £84 / night

1 / 21

Villa Neri - Cortona villa sleeps 12

Province of Arezzo / Cortona

4 bedroomsSleeps 12Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
Villa Neri is situated in San Lorenzo in close driving proximity to Cortona. Cortona is an antique Etruscan town which lies in the heart of the Chiana valley. You can even see the town perched on the hill in front of you. The position is isolated and it will offer you c  …see more

from £108 / night

£750 - £1667 / week

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from £108 / night

(5) Excellent 

1 / 4

Tranquil villa in Tuscan town of Cortona with private pool, terrace and nearby golf course

Province of Arezzo / Cortona

4 bedroomsSleeps 77 nights min stay

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This is a place to enjoy an authentic Tuscan experience. Close to the historic town of Cortona and set in acres of olives and pastures - this beautiful 17th century newly renovated Mill House with private pool has been painstakingly restored and provides an authentic t  …see more

from £229 / night

£1600 - £2140 / week

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from £229 / night

1 / 100

Panorama - Cortona villa sleeps 8

Province of Arezzo / Cortona

5 bedroomsSleeps 87 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
ExteriorVilla Panorama is a 17th century farmhouse immersed in an oasis of peace and silence, yet near important and lively cultural centres such as Cortona, Arezzo, Siena and Perugia. From the large panoramic terrace you can admire the beautiful landscape of the Chiana  …see more

from £378 / night

£2642 - £3134 / week

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from £378 / night

1 / 35

Casa Fontelunga, ancient tuscan villa with pool

Province of Arezzo / Cortona

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Casa Fontelunga is a lovely country house placed in an enchanted location hillside, between our olive plantation and just a few minutes from the beautiful art city of Cortona, made famous worldwide from the book and movie 'Under the Tuscan Sun'.Privacy and qui  …see more

from £193 / night

£1125 - £1875 / week

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from £193 / night

(8) Very Good 

1 / 20

Tuscan villa with private pool and garden and breathtaking countryside views

Cortona / Mercatale di Cortona

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 23 km; Swimming pool; Great for children of all ages ;
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 £122 / night

£849 - £1999 / week

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from £122 / night

1 / 101

Casa Medicea - 8 pax - Cortona apartment sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 180 km; Great for children of all ages ; No pets allowed;
This apartment is much larger at 250sqm and can accommodate 8 guests comfortably. The apartment´s rooms can be found on the first, second and third floors of the house.The first floor houses three double bedrooms. These are elaborately decorated, all in a unique style  …see more

from £234 / night

£1634 - £1867 / week

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from £234 / night

(1) Excellent 

1 / 13

LE MURA ETRUSCHE - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
THE CHARM OF THE MIDDLE AGES-Etruscan walls, a wonderful and relaxing view over the Chiana Valley from the beautiful terrace, above the Etruscan walls.A building of 1200 decorated with love between ancient and modern, a garden that is based on the Etruscan walls, after  …see more

from £55 / night

£375 - £542 / week

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from £55 / night

(1) Very Good 

1 / 24

Villa Calcinaio - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 30 km; Swimming pool;
Awarded as one of the prettiest and most comfortable villas in Tuscany, Villa Calcinaio with its private swimming pool stands proudly in Cortona and offers amazing views over the Chiana Valley as well as the Church of "Santa Maria delle Grazie al Calcinaio", from which  …see more

from £66 / night

£458 - £1564 / week

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from £66 / night

1 / 21

Peschino - Teverina villa sleeps 12

Cortona / Teverina

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Casa Peschino sits on the lower slopes of a quiet side valley, with stunning and extensive views over the green countryside of woods, vineyards, olive groves and farmland. It is reached by a short track through fields of sunflowers, wild flowers, maize and tobacco plant  …see more

from £246 / night

£1720 - £2710 / week

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from £246 / night

(4) Excellent 

1 / 14

Borgo di Vagli - Mercatale di Cortona house sleeps 6

Cortona / Mercatale di Cortona

2 bedroomsSleeps 6Min stay varies

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

from £109 / night

£625 - £750 / week

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from £109 / night

1 / 24

Province of Arezzo / Cortona

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £200 / night

£1250 - £1667 / week

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from £200 / night

(4) Very Good 

1 / 23

Renovated Tuscan villa rental with wonderful views and pool

Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £84 / night

£917 - £1084 / week

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from £84 / night

(2) Excellent 

1 / 24

Six bedroom traditional Tuscan villa in Cortona, a

Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 135 km; Swimming pool; Great for children of all ages ;
With a history dating back to the 17th century, this recently renovated villa distinguishes itself not only by its traditional architectural features and elegant antique furnishings, but above all by its unequalled setting. Perched on the terraced slopes of olive groves  …see more

from £377 / night

£2634 - £3400 / week

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from £377 / night

1 / 39

La Torre degli Elci - Cortona villa sleeps 12

Province of Arezzo / Cortona

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Villa Torre degli Elci is set in the greens of the Tuscan countryside, midst olives and cypress trees and just 4 km from Cortona. The name of the Villa derives from the old sighting tower which has testimonials from 13th and 14th century and which became a monastery and  …see more

from £286 / night

£2000 - £3417 / week

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from £286 / night

(1) Excellent 

1 / 24

Il Cipresso apt in farmhouse with swimming pool

Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Casa Contea was created from an old farmhouse dating back to 1800, completely renovated. With its stone walls, the courtyard, the wooden beams, you can recreate the atmosphere of the ancient past, combined with the comfort of our days. Its elevated position, surrounded  …see more

from £109 / night

£709 - £1084 / week

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from £109 / night

(1) Excellent 

1 / 24

Beautiful villa with pool and amazing Tuscan view

Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 161 km; Swimming pool; Great for children of all ages ;
Villa Cortona is a beautifully restored luxury tuscan villa with 5 double bedrooms and 6 bathrooms.Each bedroom has its own different style and character and en-suite bathroom with wonderful views.The interior of Villa Cortona is large, bright and spacious, with two lar  …see more

from £422 / night

£2950 - £4700 / week

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from £422 / night

(1) Excellent 

1 / 19

Le Casine - Olivo Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £59 / night

£409 - £552 / week

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from £59 / night

(1) Very Good 

1 / 31

IL CASALE DI CARMINA - Mercatale di Cortona villa sleeps 10

Cortona / Mercatale di Cortona

5 bedroomsSleeps 104 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Located 800 meteres above sea level, overlooking the Val di Pierle, which is the most eastern area of the town of Cortona, in the tranquillity of the verdant Hills of Tuscany, IL CASALE DI CARMINA is an old mansion completely restored and furnished in a rustic style wit  …see more

from £167 / night

£1000 / week

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from £167 / night

1 / 31

Luxury villa in Cortona - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
This magnificent villa is located at 400 m from the lovely 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. This elegant vill  …see more

from £393 / night

£2750 - £4334 / week

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from £393 / night

(4) Excellent 

1 / 4

Family Tuscan Villa Private Pool, Lovely Views

Province of Arezzo / Cortona

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
For those who enjoy privacy, this beautifully restored traditional Tuscan farm house and Private Pool, offers the opportunity experience real Tuscan living. The house has 3- 4 bedrooms ( 2 double bedrooms, 1 twin bedroom and an option of a further bed in the study), t  …see more

from £209 / night

£1459 - £2075 / week

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from £209 / night

1 / 29

Villa Le Contesse - Cortona villa sleeps 20

Province of Arezzo / Cortona

10 bedroomsSleeps 207 nights min stay

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Nearest beach 15 km; Swimming pool; Great for children of all ages ;
Villa Le Contesse is a beautiful independent villa lying on a hillside, a few minutes from the Etruscan town of Cortona. A large park with holm-oaks and secular trees surrounds the villa, which commands a stunning view over the Valdichiana. Le Contesse has been furnishe  …see more

from £536 / night

£3750 - £5357 / week

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from £536 / night

(1) Excellent 

1 / 20

Le Casine - Lavanda Apartment - Fratta Santa Caterina apartment sleeps 3

Cortona / Fratta Santa Caterina

2 bedroomsSleeps 3Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £50 / night

£390 - £523 / week

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from £50 / night

(24) Excellent 

1 / 31

Province of Arezzo / Cortona

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Beach / lakeside relaxation; Not suitable for children; Car not necessary;
 …see more

from £50 / night

£317 - £470 / week

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from £50 / night

(1) Excellent 

1 / 44

Il Ciliegio - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Wonderful and elegant villa situated in a quiet position on the green hills which surround Cortona.The villa is situated within a large property and offers wonderful views on the surrounding countryside of Tuscany.The house is tastefully furnished and is equipped with a  …see more

from £145 / night

£1014 - £1667 / week

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from £145 / night

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