Cortona Villas, Holiday rentals and apartments

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  • Italy
  • Tuscany
  • Province of Arezzo
  • Cortona

Location

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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 / 16

Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Great for children of all ages ;
 …see more

from £55 / night

£359 - £513 / week

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from £55 / night

1 / 100

Reggia Etruria - Giunone - Cortona apartment sleeps 8

Province of Arezzo / Cortona

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Apartment Giunone is an independent apartment in Tuscany with private access from the garden. The interios of the apartment are adorned with original antique furniture. The three large bedrooms enjoy wonderful views of Tuscany. Two bedroom are  queen size double, w  …see more

from £70 / night

£484 - £625 / week

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from £70 / night

(1) Excellent 

1 / 53

La Terrazza sulla Valle - Cortona apartment sleeps 6

Province of Arezzo / Cortona

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
Beautifully freshly renovated 2 bedroom/2 bathroom apartment with a private terrace overlooking the Valley. Master bedroom with a big mirror closet, fireplace, stunning view of the valley from the window and access to private terrace. The other bedroom has a closet an  …see more

from £134 / night

£750 - £984 / week

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from £134 / night

(2) Excellent 

1 / 37

Province of Arezzo / Cortona

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; Air conditioning;
 …see more

from £59 / night

£417 - £650 / week

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from £59 / night

1 / 19

Le Casine - Mela 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 £51 / night

£352 - £466 / week

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from £51 / night

1 / 31

Villa Nello - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Above the wood oven is engraved 1781. Villa Nello was restored in 2001. It develops on three floors, sleeping 8 people, plus a small independent single bedroom with bathroom. The ground floor includes an entrance foyer, adjoining dining room and kitchen leading to a lar  …see more

from £596 / night

£4167 / week

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from £596 / night

1 / 30

Province of Arezzo / Cortona

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £328 / night

£2292 - £3209 / week

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from £328 / night

1 / 34

Villa le Contesse - 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 ; No pets allowed;
Villa Mariani is situated on the hillside leading up the eastern flank of Cortona, while the town is just 5 minutes away by car or 20 minutes on foot. A large park with holm-oaks and pine trees surrounds the villa, which commands a stunning view over the Valdichiana. T  …see more

from £536 / night

£3750 - £5357 / week

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from £536 / night

1 / 18

GLI ARCHI - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
It 'a beautiful cottage completely restored, was once a barn and a tobacco warehouse. now has 2 bedrooms, a lounge, a kitchen, 2 bathrooms and a dining room that can become an extraordinary study. It has a swimming pool, a large garden, a bocce court, private parki  …see more

from £67 / night

£834 - £1167 / week

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from £67 / night

1 / 14

Le Casine - Bugia 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 £51 / night

£352 - £466 / week

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from £51 / night

1 / 26

VILLA CORTONA (SOFIA) 13 BEDROOMS - Fratticciola farmhouse sleeps 29

Cortona / Fratticciola

13 bedroomsSleeps 29Min stay varies

  • 13 bedrooms
  • Sleeps 29
  • Min stay varies
Key info: Beach / lakeside relaxation; Not suitable for children; Air conditioning;
Villa Sofia in the innermost heart of the Tuscan countryside.It joins its peaceful landscape to the neighbourhood with important artistic, cultural cities like CORTONA 7km, AREZZO 24kmMONTEPULCIANO 20Km (Chianti Wine) ,PIENZA 25 Km(cheese), LAKE TRASIMENO 18km, ASSIS  …see more

from £459 / night

£3250 - £5542 / week

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from £459 / night

(2) Very Good 

1 / 12

Cortona villa in beautiful Tuscan countryside

Province of Arezzo / Cortona

3 bedroomsSleeps 57 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
The sitting room has an old open fireplace and impressive, ancient wooden beams. Two comfy sofas are a nice modern addition! The dining room is authentic Italian 1950s decor under more seriously ancient ceiling beams. The atmosphere at San Silvestro is one of homely cou  …see more

from £93 / night

£650 - £1090 / week

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from £93 / night

1 / 42

Casa Fiordaliso - Cortona house sleeps 4

Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 9 km; Great for children of all ages ; Car advised;
Casa indipendente, con uno stupefacente panorama. Potrete mangiare all'aperto gustando la bellezza della Valdichiana e di Cortona, sfondo su cui si staglia la figura del Palazzone, villa principesca del 1500 con la sua torre ed il suo muro merlato.In assoluta privacy,  …see more

from £78 / night

£547 - £715 / week

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from £78 / night

(34) Excellent 

1 / 25

Il Villino di Cortona (Property at exclusive use)

Province of Arezzo / Cortona

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 150 km; Swimming pool; Great for children of all ages ;
"Il Villino di Cortona", cosy holiday home nestled in the green heart of the Chiana Valley in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in contact with nature ... "Il Villino di Cortona”, is a small holiday home, nestled in the Va  …see more

from £80 / night

£500 - £717 / week

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from £80 / night

1 / 19

Province of Arezzo / Cortona

15 bedroomsSleeps 30Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £767 / night

£5417 - £8334 / week

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from £767 / night

(1) Excellent 

1 / 14

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 ; Air conditioning;
 …see more

from £55 / night

£238 - £367 / week

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from £55 / night

1 / 34

Cortona / Montanare

1 bedroomSleeps 3Min stay varies

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

from £59 / night

£375 - £500 / week

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from £59 / night

1 / 26

Villa la Bozza - Montalla farmhouse sleeps 14

Cortona / Montalla

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Nearest beach 200 km; Swimming pool; Great for children of all ages ;
I our farm we have a number of houses left intact in theyr original stile.Viila la Bozza is ancient building near a small country village in the country in front of Cortona.Divided in 2 apartments of the same size, completely independent from each other you will have a  …see more

from £267 / night

£1413 - £2508 / week

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from £267 / night

(8) Excellent 

1 / 35

Villa Nobile is a stunning 19th Century Villa

Province of Arezzo / Cortona

7 bedroomsSleeps 243 nights min stay

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min stay
Key info: Nearest beach 250 km; Swimming pool; Great for children of all ages ;
Villa Nobile is a stunning 19th Century classical style villa recently restored authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land. A private avenue of young cypresses bringing you to our doorstep. Tran  …see more

from £63 / night

£459 / week

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from £63 / night

(2) Excellent 

1 / 34

Luxury Villa in Cortona 8 - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 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 £340 / night

£2375 - £3500 / week

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from £340 / night

1 / 25

Casale della Torre - Cortona villa sleeps 10

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 ; No pets allowed;
Villa Casale Mulino is a property situated on about 10 acres of terraced land which has olive tree groves and vineyards. It's a perfect starting point for panoramic walks or biking. The spectacular panorama that this villa offers will be the missing ingredient for  …see more

from £341 / night

£2384 - £3400 / week

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from £341 / night

(3) Very Good 

1 / 24

Casale il Granaio - Cortona apartment sleeps 6

Province of Arezzo / Cortona

4 bedroomsSleeps 6Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Great for children of all ages ;
The barn was the enchanted place of my youth rushes, when I grew up I realized the dream which was of my grandfather before and after of my dad.Welcome to “Casale il Granaio”A magic place in the heart of Valdichiana...In the heart of Valdichana, bordering on Umbria,  …see more

from £69 / night

£417 - £530 / week

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from £69 / night

(10) Excellent 

1 / 24

Home-from-home comfort in the Tuscan hills

Cortona / Ruffignano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
Get above and beyond the rat race in our cottage-style retreat! Here we offer self catering holidays in spacious, well presented accommodation that spans two levels of our secluded farm cottage, with its beautifully landscaped pool, located in tranquil hills 12 km (plu  …see more

from £109 / night

£730 - £1725 / week

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from £109 / night

(2) Very Good 

1 / 19

Le Casine - Limone Apartment - Fratta Santa Caterina apartment sleeps 4

Cortona / Fratta Santa Caterina

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • 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 £63 / night

£438 - £600 / week

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from £63 / night

(3) Excellent 

1 / 21

Tuscan Family Villa Castiglioni, Pool easy access

Province of Arezzo / Cortona

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 26 km; Swimming pool; Great for children of all ages ;
This exceptional, luxurious and impeccable private estate in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Extraordinary views of both the famed Montechio Castle and, the Eternal Tuscan hill town of Castiglion Fiorentino can be easily  …see more

from £446 / night

£3120 - £4225 / week

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from £446 / night

1 / 22

The Orangery: Cortona holiday villa with private pool and garden

Province of Arezzo / Cortona

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
“The Orangery” is a charming and cosy detached house wisely set in a large property against a breathtaking landscape that includes an additional accommodation facilities. Each one has its own private garden, swimming pool and spaces for exclusive use to completely r  …see more

from £163 / night

£709 - £1246 / week

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from £163 / night

1 / 24

Fattoria Borgonuovo - Rosa - 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 / 36

Villa Orlando - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Lovingly restored in 2004 Villa Orlando sleeps 8 people comfortably with four bedrooms, all with en-suite bathrooms with showers. This villa is perfect for families or groups that like to spend time enjoying the outdoors.You will enjoy a spacious , fully equipped kitche  …see more

from £274 / night

£1917 - £3455 / week

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from £274 / 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 ; No pets allowed;
 …see more

from £106 / night

£715 - £757 / week

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from £106 / night

(1) Excellent 

1 / 10

ETRUSCA - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 bedroomSleeps 31 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Great for children of all ages ; Pets welcome;
Dopo il positivo riscontro per le Mura Etrusche, Gian Luca e Lucia hanno il piacere di proporvi una nuova struttura, Etrusca.La casa, situata nel centro storico di Cortona, lungo Via Nazionale detta "Ruga Piana", strada principale, che unisce Piazza della  …see more

from £77 / night

£542 / week

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from £77 / night

1 / 17

Villa Corte - Mercatale di Cortona villa sleeps 8

Cortona / Mercatale di Cortona

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
Villa Corte is an enchanting property, skillfully restored to maintain its ancient charm. It is situated inside the Micheli Estate and entirely furnished in an authentically tuscan style with exposed wooden beam cielings, terracotta floors and a stone fireplace.Villa Co  …see more

from £480 / night

£1917 - £2646 / week

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from £480 / night

(1) Excellent 

1 / 88

Province of Arezzo / Cortona

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 18 km; Swimming pool;
 …see more

from £101 / night

£606 - £841 / week

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from £101 / night

(3) Very Good 

1 / 11

Splendid flat in Tuscany, pool & breathtaking view

Cortona / Mercatale di Cortona

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 12 km; Swimming pool; Suitable for children age 5+;
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 £131 / night

£917 / week

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from £131 / night

(1) Good 

1 / 24

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 ; Car not necessary;
 …see more

from £55 / night

£606 - £765 / week

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from £55 / night

1 / 30

1 bedroom sleeps 4, beautiful view - Cortona house sleeps 4

Province of Arezzo / Cortona

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 15 km; Suitable for children age 5+; Car advised;
A beautiful and comfortable typical Cortona country farmhouse. This nice accommodation is situated 5 minutes by car far from the historic hill town of Cortona. The house is over a hundred years old and constructed of local river rock, the walls are up to a meter thick.  …see more

from £63 / night

£334 / week

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from £63 / night

1 / 20

Province of Arezzo / Cortona

4 bedroomsSleeps 12Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Car advised;
 …see more

from £169 / night

£1093 - £2404 / week

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from £169 / night

(2) Excellent 

1 / 20

Ca de Muito, a peaceful Tuscan cottage with breathtaking views and a private outdoor pool

Cortona / Mercatale di Cortona

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 20 km; Swimming pool; Great for children of all ages ;
Charming Ca de Muito has an idyllic position on the Tuscany side of the Niccone Valley. The views of the stunning countryside are breath-taking, they stretch over the Niccone Valley including 2 picturesque castles, to the village of Preggio on the opposite hillside. W  …see more

from £146 / night

£1021 - £1433 / week

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from £146 / night

1 / 15

Le Casine - Papavero 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 £54 / night

£371 - £495 / week

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from £54 / night

1 / 42

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 ; Air conditioning;
 …see more

from £67 / night

£463 - £841 / week

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from £67 / night

1 / 30

Province of Arezzo / Cortona

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 13 km; Swimming pool; Great for children of all ages ;
 …see more

from £55 / night

£344 - £446 / week

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from £55 / night

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