Villas in Cortona and holiday rentals – Holiday Lettings - Holiday Rentals Cortona

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390 Holiday homes

1 / 22

Casa Danielle, Tuscan Retreat - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 28 km; Swimming pool; Child friendly ;
A lovely home from Home in Tuscany with Private Pool with amazing views A relaxed and comfortable vacation home in the heart of the Tuscan countryside.Just outside the enchanting town of Castiglion Fiorentino near Cortona, Arezzo, Florence, Siena and Perugia is Casa Dan  …see more

from £141 / night

£983 / week

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from £141 / night

(2) Excellent 

1 / 20

Ca de Muito, a peaceful Tuscan cottage with breathtaking views and a private outdoor pool - Mercatale di Cortona cottage sleeps 6

Cortona / Mercatale di Cortona

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 20 km; Swimming pool; Child friendly ;
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 / week

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from £146 / night

1 / 29

Il nido, lovely tuscan cottage with pool - Pietraia cottage sleeps 4

Cortona / Pietraia

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Child friendly ; Pet friendly;
Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, Il Nido is a lovely small villa recently restored and finely appointed with a contemporary country-chic style. The skillful ability in matching the soft tones and the tasteful reca  …see more

from £105 / night

£727 - £1710 / week

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from £105 / night

1 / 84

Fienile/luxury. Private village. Sleeps 5 - Montecchio house sleeps 5

Cortona / Montecchio

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Fienile Cottage is a cute detached cottage, situated in its own private garden, with sensational views of olive groves, vineyards, meadows full of sunflowers, poppies and purple cornflowers, spiralling infinitely into the valleys below. It has 1 double bedroom + 1 singl  …see more

from £116 / night

£812 - £941 / week

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from £116 / night

1 / 18

Rustic two bedroom Tuscan apartment close to Cortona's main square, wifi and parking available - Cortona apartment sleeps 2

Province of Arezzo / Cortona

2 2 1 night min stay

  • 2 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Ask owner if suitable for children;
Quintani Sole - central apartmentApartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. WIFI, TV led, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square a  …see more

from £69 / night

£428 / week

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from £69 / night

(1) Very Good 

1 / 22

Villino Laura - Montecchio villa sleeps 4

Cortona / Montecchio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 155 km; Swimming pool; Child friendly ;
Villino Laura is an old mill immersed in the picturesque green Tuscan countryside only few kilometres from Cortona and has been completely restored maintaining its original charm. The furnishing of this property makes it one of a kind for its class, due to its precious  …see more

from £134 / night

£778 - £1112 / week

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from £134 / night

(22) Excellent 

1 / 16

Province of Arezzo / Cortona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Pet friendly;
 …see more

from £60 / night

£359 - £684 / week

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from £60 / night

(2) Very Good 

1 / 24

Idyllic Tuscan villa with annexes, outdoor pool an - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 140 km; Swimming pool; Child friendly ;
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 £231 / night

£1616 - £1958 / week

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from £231 / night

1 / 14

La Piccionaia - Cortona apartment sleeps 5

Province of Arezzo / Cortona

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
“Le Gelosie apartments” are the natural and inviting alternative to our hospitality and combine good taste and attention for details.The materials, the colours and the spaces were studied to satisfy the esthetical pleasure along with the natural need for comfort. Th  …see more

from £171 / night

£1197 / week

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from £171 / night

1 / 24

35753-Holiday house Lake Trasi - Mercatale villa sleeps 15

Cortona / Mercatale

7 15 7 nights min stay

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
Farmhouse surrouned by the green Umbria countryside,<br>bordering on Tuscany. The farmhouse is divided in 3, intereconnected,<br>apartments, accommodating in total 15 persons, with 3 bathrooms of which one<br>with bath tub, 6 double bedrooms, 1 bedroom  …see more

from £161 / night

£1123 - £1420 / week

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from £161 / night

1 / 30

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

Province of Arezzo / Cortona

1 4 1 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 £65 / night

£342 / week

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from £65 / night

1 / 17

Province of Arezzo / Cortona

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
 …see more

from £65 / night

£436 - £496 / week

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from £65 / night

1 / 5

Cortona / Mercatale di Cortona

4 10 3 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
 …see more

from £30 / night

£513 / week

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from £30 / night

1 / 8

La Tesa Girasole - Farinaio apartment sleeps 4

Cortona / Farinaio

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
The apartment Girasole is situated on the ground floor and it has a separate entrance. It consists of: a living room, a kitchen, two bedrooms, two bathrooms with shower and independent heating.Apartment cleaning, detergents and waste:We use non-toxic cleaning products a  …see more

from £35 / night

£684 / week

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from £35 / night

1 / 12

Quintani Sole - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Child friendly ; Ask about pets;
THE APARTMENT Apartment for 2 person and 1/2, compose by one bedroom + lounge with kitchen + 2 bathroom. internet wifi, TV led, microwave, washing machine, toaster, kettle, spinner, central heating is providing, in the summer months cool fresh air is inside. Central po  …see more

from £60 / night

£428 / week

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from £60 / night

1 / 89

Querce/luxury. Private village. Sleeps 5 - Montecchio house sleeps 5

Cortona / Montecchio

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
QUERCE COTTAGE is one of two dwellings in a large cottage, overlooking the private village, Garden Of Eden, the hills, dales, olive groves and vineyards as the vista spirals into a haze of greens, dotted with colours, an infinity of brightly coloured patchwork, against  …see more

from £20 / night

£135 - £941 / week

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from £20 / night

1 / 7

LA TESA Olivo - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees.Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating e  …see more

from £35 / night

£471 / week

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from £35 / night

(8) Excellent 

1 / 35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

Province of Arezzo / Cortona

7 24 3 nights min stay

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min stay
Key info: Nearest beach 250 km; Swimming pool; Child friendly ;
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 £65 / night

£471 / week

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from £65 / night

1 / 13

Cortona / Montecchio

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Child friendly ; Pet friendly;
 …see more

from £127 / night

£889 - £1556 / week

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from £127 / night

1 / 16

YPR LOFT 21 - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
This apartment is stylish and extremely comfortable and it is located in the heart of Cortona. Maintaining the Tuscan features of the town's buildings, it's been newly restored with great elegance and equipped with all modern conveniences. Its central, but, still, qui  …see more

from £599 / night

£4189 / week

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from £599 / night

1 / 14

Villa Cuiano - La Loggetta - Mercatale di Cortona apartment sleeps 3

Cortona / Mercatale di Cortona

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 12 km; Swimming pool; Child friendly ;
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 £69 / night

£428 - £471 / week

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from £69 / night

1 / 12

Quintani Luna - Cortona apartment sleeps 2

Province of Arezzo / Cortona

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 20 km; Ask owner if suitable for children;
QUINTANI LUNAApartment for 2 person, compose by one bedroom + kitchen + 1 bathroom with shower. WIFI, TV, microwave, washing machine, toaster, kettle. Central position, near public parking and restaurants. Only 3 minute from main square and grocery.THE HISTORICAL BUILD  …see more

from £69 / night

£428 / week

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from £69 / night

1 / 18

Villa Petrischio - Cortona apartment sleeps 6

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; Air conditioning; No pets allowed;
You can find Villa Petrischio in the heart of Tuscany. The Villa was built in the 18th century on the highest hill of Farneta, which is a little village ten miles away from Cortona. Villa Petrischio is surrounded by three hectares of park with secular pines and cypresse  …see more

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Pricing unknown

1 / 4

Province of Arezzo / Cortona

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £60 / night

£385 / week

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from £60 / night

1 / 10

Grecale - PI2012_226 - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 3 7 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Nearest beach 140 km; Swimming pool; Child friendly ;
Grecale is a part of the beautiful apartment complex, Poggio al Vento. The apartments are located in the same farmstead, which has been tastefully renovated to retain much of the original character and features. Ideal for a couple or a family, the apartments retain a wa  …see more

from £55 / night

£385 - £677 / week

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from £55 / night

1 / 12

La Tesa Uva - Farinaio apartment sleeps 4

Cortona / Farinaio

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
You will find 4 spacious apartments for your stay in Cortona, bright and comfortable and an outbuilding between the olive trees.Farmhouse La Tesa is the best that a country house can give you for your holiday in the heart of Tuscany. You will experience a rejuvenating e  …see more

from £35 / night

£624 / week

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from £35 / night

(1) Excellent 

1 / 10

ETRUSCA - Cortona apartment sleeps 3

Province of Arezzo / Cortona

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
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 £79 / night

£556 / week

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from £79 / night

1 / 7

Appartamento in Sant' Angelo di Cortona - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Apartment Sant' Angelo in Cortona is a bright and spacious one bedroom apartment reconstructed from an ancient olive mill. Chestnut beams, terracotta tiles and antique stone all in typical Tuscan style, full of character, offering guests a warm vacation home.The ap  …see more

from £86 / night

£599 / week

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from £86 / night

1 / 16

Tuscan hideaway: charming rural villa with pool and spectacular views, sleeps 4 - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
A special hide-away in Tuscany ! Casa Serena is a really charming little house/villa is set in the middle of olive grove and surrounded Tuscan woodland, and provides privacy and serenity for a truly relaxing vacation. During Autumn and winter, there are the spectacular  …see more

from £93 / night

£648 - £977 / week

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from £93 / night

(1) Excellent 

1 / 24

Il Moro Novo - Montalla apartment sleeps 3

Cortona / Montalla

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Swimming pool; Child friendly ; 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 £60 / night

£314 - £593 / week

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from £60 / night

(31) Excellent 

1 / 21

Tuscan Villa. Borgo Valecchie. Cortona - Montanare villa sleeps 10

Cortona / Montanare

4 10 5 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Child friendly ;
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £201 / night

£1411 - £2522 / week

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from £201 / night

1 / 18

Tuscany traditional 3 bedroom farmhouse - Cortona farmhouse sleeps 9

Province of Arezzo / Cortona

3 9 7 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Ask about pets;
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 - £1495 / week

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from £157 / night

(5) Excellent 

1 / 24

Gorgeous five bedroom villa, game room, outdoor p - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; 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 £143 / night

£1000 - £3112 / week

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from £143 / night

1 / 16

Charming townhouse close to historic centre - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 6 km; Suitable for children age 5+;
'Piccolo Porta' is situated in Cortona and can be found a few minutes stroll from centro storico with its galleries, wonderful shops and great restraunts. The beautiful medieval streets lead you to Piccolo Porta where from the second floor you can see over the  …see more

from £72 / night

£500 / week

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from £72 / night

(3) Excellent 

1 / 30

Poggiobello - Cortona cottage sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
The cottage is immersed in the splendid countryside with breathtaking views all around. It is surrounded by the lovelyundulating hills covered with sunflowers, olive groves and cypresses, you will find yourself totally immersed in an enchanted atmosphere frozen in time.  …see more

Pricing unknown

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1 / 9

Il Borgo Agritourism - Cortona apartment sleeps 4

Province of Arezzo / Cortona

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
The il Borgo Agritourism Complex is near the historic Etruscan city of Cortona. It is in a beautiful country setting amongst olive trees, cypresses and sunflowers in the Chiana Valley. There is a spacious garden and a communal swimming pool. The agritourism complex is e  …see more

from £171 / night

£1026 / week

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from £171 / night

1 / 13

Province of Arezzo / Cortona

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Car essential; Pet friendly;
 …see more

from £43 / night

£257 - £342 / week

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from £43 / night

(1) Excellent 

1 / 10

Il ponticello - Cortona apartment sleeps 4

Province of Arezzo / Cortona

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Car advised; Ask about pets;
The house takes its name from the bridge which gives access to the premises(il ponticello means, in fact,little bridge).The house is located in village Torreone, in the town of Cortona, which is only 2 km far, that can also be walked on foot. It's in the green,on a  …see more

from £43 / night

£257 - £377 / week

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from £43 / night

1 / 16

Palazzo Cinotti Suite Giulio - Cantalena apartment sleeps 2

Cortona / Cantalena

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Ask owner if suitable for children; Air conditioning; No pets allowed;
Suite Giulio is a beautiful apartment right in the city centre of Siena, between the Cathedral and Piazza Il Campo. Renewed in 2013 offer all the modern comfort, tv sat, wi fi, air conditioned, new bed etc. The aparment is full of light, has frescoes, a big living room  …see more

from £163 / night

£975 / week

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from £163 / night

1 / 16

Province of Arezzo / Cortona

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
 …see more

from £56 / night

£368 - £428 / week

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from £56 / night

Top Destination reviews

Stunning Tuscan villa with five bedrooms, private
A true TUSCAN experience. Better than words can describe.

It is quite a challenge to put into words a description of this place, the family and the amazing time we had at Vila Papale. The house and the entire property has so much history and character making this place a unforgettable experience. The garden … see more
villa ai cedri
A marvellous house with a beautiful panorama view

A beautiful house in a peaceful area with a wonderful view to the valley. There are lovely rooms with tasteful furniture. Although the owners live next door, they do not disturb at all, they are really friendly and helpful any time you need somethin … see more
To Stones
Amazing Home Away From Home

The best first impression was to be greeted late at night by Ester and her partner in the dark and in poor weather just so we could find a parking spot and get situated in the property. Ester was amazing and has gone to great lengths to ensure her ho … see more

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