Villas with a pool Cortona | Apartments to rent with swimming facilities

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona

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  • Bagnolo (3)
  • Capezzine (2)
  • Cegliolo (5)
  • Centoia (7)
  • Farinaio (3)
  • Fratta Santa Caterina (9)
  • Fratticciola (11)
  • Localita Mucchia (2)
  • Mercatale (4)
  • Mercatale di Cortona (16)
  • Montalla (15)
  • Montanare (7)
  • Montecchio (13)
  • Montecchio, San Lorenzo (2)
  • Pietraia (6)
  • Poggioni (4)
  • Ruffignano (1)
  • Teverina (6)

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501 Holiday homes

Filters applied: Swimming pool (501)

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1 / 78

Cortona / Centoia

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 £93 / night

£589 - £673 / week

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from £93 / night

1 / 18

Acero, pleasing hilly cottage among olive grove

Province of Arezzo / Cortona

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Car essential;
Acero is a cosy apartment that belongs to a beautiful hillside property, Col di Leccio, an authentic farmhouse where nature and silence dominate. Acero is made up of a double bedroom, a bedroom with twin beds, a bathroom with a shower, a kitchen and a living room. There  …see more

from £66 / night

£459 - £709 / week

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from £66 / night

1 / 100

Residence Valdichiana - 4 pax - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
4 pax This apartment for rent in Tuscany boasts its own private garden. This apartment of the farmhouse can host up to 4 guest. The country style, the typical warmth of Tuscan hospitality make it a perfect place to experience the flavour of Tuscany. This apart  …see more

from £105 / night

£575 - £742 / week

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from £105 / night

(2) Excellent 

1 / 24

Fattoria Borgonuovo - Ortensia - 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

1 / 20

Teresa Villa Overlooking a Breathtaking Landscape

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 15 km; Swimming pool; Not suitable for children;
Villa Teresa is a pretty villa with a wonderful view on Cortona valley, completely renovated and equipped with every comfort. Very near to the nice town of Cortona, this wonderful structure overlooks on a breathtaking landscape and it is situated short distance from a s  …see more

from £179 / night

£1250 - £2625 / week

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from £179 / night

(9) Excellent 

1 / 32

Villa Rosa: Luxury Home In Cortona |WI-FI|Pool|

Province of Arezzo / Cortona

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Swimming pool;
Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close to the amenities but far enough away for privacy, seclusion and relaxation. We would love to welcome you to Villa Rosa w  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(1) Good 

1 / 37

Fattoria Le Chianacce - La Mucchia. Cortona

Province of Arezzo / Cortona

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
Set in the verdant hills of the Valdichiana on the border between the Provinces of Arezzo and Siena the Fattoria delle Chianacce is a typical farmhouse built in the last century. These farms produced some of the very best beef and pork in the area and many continue to d  …see more

from £76 / night

£530 - £841 / week

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from £76 / night

(2) Excellent 

1 / 12

Charming Cortona villa with private pool (Dardano)

Province of Arezzo / Cortona

4 bedroomsSleeps 67 nights min stay

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 £165 / night

£1150 - £1650 / week

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from £165 / night

1 / 100

Residence Valdichiana - 3 pax - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
3 pax Guests at this apartment for rent in Tuscany afford the use of their own private garden. This apartment affords a living room with dining area, a fully fitted kitchen corner. Its accommodation capacity is for 3 people as it has a double bedded room and a sing  …see more

from £75 / night

£525 - £659 / week

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from £75 / night

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Cortona (AR) - ITA637 - 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 ; No pets allowed;
Situated in Cortona this charming holiday home is the ideal place for the perfect getaway in Italy. The house comprises of 3 double beds , so it can comfortably host a group of 6 people. There are also 3 bathrooms to allow for individual comfort and privacy. There i  …see more

from £85 / night

£592 - £958 / week

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from £85 / night

1 / 19

Villa Santa Maria - Cortona villa sleeps 14

Province of Arezzo / Cortona

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Villa Santa Maria is set in a commanding location nestled amongst olive trees in the very heart of Tuscany. Villa Santa Maria is the ideal spot for guests to enjoy a relaxing holiday in Tuscany in charming and relaxing countryside surroundings far from the hustle and b  …see more

from £375 / night

£2625 - £4317 / week

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from £375 / night

1 / 21

Villa I Girasoli - Centoia villa sleeps 10

Cortona / Centoia

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 ;
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  …see more

from £137 / night

£955 - £2090 / week

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from £137 / night

(5) Excellent 

1 / 24

Gorgeous five bedroom villa, game room, outdoor p

Province of Arezzo / Cortona

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
The Cortonese hillside, La Fortezza and the ancient wall which encloses the town, dominate the view of the surrounding hillside.Guests have exclusive use of the delightful 12x6 swimming pool, with Roman steps, which lies in an extremely panoramic position and from where  …see more

from £140 / night

£975 - £3034 / week

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from £140 / night

1 / 18

Villa San Martino - Cortona villa sleeps 7

Province of Arezzo / Cortona

4 bedroomsSleeps 77 nights min stay

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Nearest beach 140 km; Swimming pool; Great for children of all ages ;
Villa San Martino is set in a delightful position among extensive grounds overlooking the countryside. The swimming pool is surrounded by olive trees and lush gardens. The nearest town is Cortona, famous for its ancient backgrounds, home town of famous painter Luca Sig  …see more

from £142 / night

£990 - £1959 / week

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from £142 / night

1 / 100

Flavia - Loggia - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
This apartment has one double bedroom with a comfortable queen bed. It has a stunning view of the hills surrounding the large hamlet. It has one large bathroom that is complete with a shower and modern amenities.There is a cozy living room&  …see more

from £83 / night

£413 - £746 / week

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from £83 / night

1 / 100

I Girasoli - 5+2 pax - Cortona apartment sleeps 7

Province of Arezzo / Cortona

3 bedroomsSleeps 72 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min stay
Key info: Nearest beach 130 km; Swimming pool; Great for children of all ages ;
This apartment near Cortona is divided into two storeys and can sleep up to 7 guests (5+2) in 130sq-m. Going up the external stairs guests arrive at a veranda for alfresco dining. From here they enter the living room equipped with sofa bed for 2 people, a kitchen wi  …see more

from £67 / night

£417 - £542 / week

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from £67 / night

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Panphilii, marvelous 18th century villa in Cortona

Province of Arezzo / Cortona

8 bedroomsSleeps 167 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Nestled in lush park surroundings, Villa Panphilii is a stunning 18th century villa located in Cortona, an ancient Etruscan city. The villa is set in breath-taking natural scenery, changing in colour and shades throughout the year, creating a unique atmosphere. There is  …see more

from £481 / night

£3362 - £4622 / week

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from £481 / night

1 / 16

Casina Vereno - Bagnolo villa sleeps 4

Cortona / Bagnolo

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
This charming independent villa is situated in panoramic position in the Cortonese Mountains above the Etruscan hill town of Cortona. It's ideal location make it easy visit the most renowned historical and art cities of Tuscany and Umbria. The property, with privat  …see more

from £145 / night

£1013 - £1371 / week

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from £145 / night

(2) Excellent 

1 / 24

Charming Tuscan Villa with private pool and garden, stunning valley views!

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 essential;
A charming cottage situated in dominant position with view of the surrounding hills covered with silver olive groves and the Valdichiana valley. The house lies in a relaxing, peaceful area and is surrounded by a large fenced garden and aromatic plants. In the garden you  …see more

from £86 / night

£600 - £2084 / week

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from £86 / night

(1) Excellent 

1 / 87

Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 18 km; Swimming pool; Great for children of all ages ;
 …see more

from £93 / night

£589 - £656 / week

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from £93 / night

1 / 24

Villa Fonte - Cortona villa sleeps 12

Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
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 £399 / night

£2792 - £4334 / week

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from £399 / night

(1) Excellent 

1 / 14

Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

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

from £100 / night

£367 - £542 / week

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from £100 / night

(2) Excellent 

1 / 25

Casa Gorgacce - Mercatale di Cortona house sleeps 6

Cortona / Mercatale di Cortona

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 22 km; Swimming pool; Great for children of all ages ;
Casa Gorgacce is an old stone farmhouse with lots of character beautifully converted with all modern comforts. It has a private garden and pool, complete privacy yet with great access and only a few kilometres from 2 lively villages; Meratale di Cortona and Lisciano Nic  …see more

from £130 / night

£822 - £1488 / week

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from £130 / night

1 / 101

Curtum - Three-Room Deluxe - Cortona apartment sleeps 5

Province of Arezzo / Cortona

2 bedroomsSleeps 51 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
The apartment is a two-story construction, and it can sleep up to 5 people.The ground floor has a large living and dining area, together with a full kitchenette and the first bathroom. On the top floor, there is one double room, one twin room and a second bathroom with  …see more

from £183 / night

£716 - £950 / week

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from £183 / night

1 / 18

Province of Arezzo / Cortona

11 bedroomsSleeps 201 night min stay

  • 11 bedrooms
  • Sleeps 20
  • 1 night min stay
Key info: Swimming pool; Suitable for children age 5+; Car advised;
 …see more

from £500 / night

£3334 / week

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from £500 / night

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

(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

(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

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