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1,820 Results  |  
19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £37 /night

£255 - £679 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
The apartment Sant'Angelo is located just below the Etruscan City of Cortona in a beautiful residential complex which has been tastefully restored, maintaining the traditional characteristics of the antique oil mill that it once was. Video footage of apartment on Youtube is available on:http://youtu.be/wR2cgZSvDOM  …see more

17 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £170 /night

£1188 - £1442 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Chosen by hundreds of guests on Tripadvisor as number one Medieval Farmhouses in Cortona, we were awarded since 2010 every year with certificate of excellency. The area also provides various facilities for outdoor activities, quad,bikes,horses,golf,tennis and more  …see more

21 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4/5 

2 Nights min stay

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from £102 /night

£710 - £1183 / week

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Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Il Bozzino, a lovely ancient Tuscan farmhouse, with swimming pool, just minutes from Cortona, beautiful medieval Tuscan town. Join the peace and traquillity of the tuscan country with the convenience of the close main roads and railroads to visit Tuscany end Umbria Azienda Fontelunga has some of the most appealing villas of the Cortona area available for rental.  …see more

Featured properties

22 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £79 /night

£552 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Casina via Iannelli offers you the opportunity to stay in the historic center of Cortona in a house of historical and artistic interest created and preserved until the beginning of 1300.  …see more

21 Photos

Farmhouse | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £118 /night

£823 - £1010 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Perfect location for combining art and relax in a friendly atmosphere. Newly restored .The owners live in the main building and are available for any needs. Free vegetables from the vegetable  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £122 /night

£848 - £1230 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
La Fenice is part of a beautiful restored farmhouse, contained in private walled and hedged, landscaped gardens. Romantic, family and site seeing, all are catered for, plus use of the magnificent 20mX 8m swimming pool. makes an ideal holiday location for everyone. Part of the privately owned I Casali di Montecchio, there are wonderful views of Cortona from the garden.  …see more

7 Photos

House | 2 Bedrooms | sleeps 7

4 Nights min stay

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from £43 /night

£297 - £594 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
  • Private garden
Excellently located house at the foot of the Chianti hills and close to the most popular Tuscan sites!  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

2 Nights min stay

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from £546 /night

£3816 - £4664 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Il Molino offre un veloce servizio internet ad alta velocitá,una piscina esterna di 17 mt con idromassaggio,2 camere suite con bagni grandi e funzionali,il tutto circondato da un grande giardino.Il cliente verrá accolto da una cena offerta dal proprietario. Il pacchetto di soggiorno comprende un ingresso omaggio a persona alle vicine Terme di Rapolano.  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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Key info:

  • Not suitable for children
  • Car essential
  • No pets allowed
A step away from Florence and the Chiantishire  …see more

11 Photos

Apartment | 4 Bedrooms | sleeps 5

2 Nights min stay

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from £79 /night

£552 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
Welcome to “Casale il Granaio”, a magic place in the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno lake and in the middle between the cities of Arezzo and Perugia. From here is easy also to reach Montepulciano, Siena, Pienza, Rapolano and Spoleto.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £104 /night

£724 - £1327 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
The beautifully decorated Tuscan-villino is surrounded by cypresses, old pines and olive trees, the residences offer magnificent views of the enchanting Valdichiana, a rolling countryside of sunflowers and vineyards. Excellent Restaurant by the pool .  …see more

15 Photos

Apartment | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £61 /night

£424 - £689 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Suitable for children over
  • Car not necessary
  • No pets allowed
historic and cultural holiday for couples or individuals. minutes walk to Cortona centre, traditional restored property; great location for touring other parts of Tuscany, sleeps up to 6, organised tour  …see more

7 Photos

Farmhouse | 6 Bedrooms | sleeps 6

2 Nights min stay

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from £73 /night

£505 - £844 / week

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Key info:

  • Nearest beach 150 km
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
The farmhouse is located on the oriental Chianti's hills, in the middle of triangle Siena-Arezzo-Firenze.The apartment has 2 double bedroom, 2 bathrooms an open kitchen/dining room with a double sofa bed. Direct access to a terrace equipped by the pool.  …see more

14 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £146 /night

£1017 - £2120 / week

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Key info:

  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Holiday property located in Tuscany in Castiglion Fiorentino. Close location to many touristic attractions like Cortona, Arezzo, Siena, Montepulciano, Montalcino, Chianti, Florence and many more makes it a fantastic place for family holidays.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

1 night min stay

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from £38 /night

£263 - £2120 / week

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Key info:

  • Nearest beach 150 km
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
Villa Giarradea is the perfect choice for all the people want to spend a beautiful vacancy completely immersed in the peace of the Tuscan nature, without give up to the comfort. The Villa is really near to beautiful trekking, but at just 10 minutes by car from Cortona  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 6

4 Nights min stay

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from £48 /night

£331 / week

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Key info:

  • Nearest beach 170 km
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
We'd like you to spend your next holiday here with us in our "il Cuniglio" residence located in the slopes of the Casentino region, Tuscany. Discover the fabulous art, the rich history and culture of this area regenerating mind and spirit in our luscious countryside.  …see more

11 Photos

Farmhouse | 4 Bedrooms | sleeps 4

1 night min stay

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from £52 /night

£361 - £653 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
The farmhouse is located on the oriental Chianti's hills, in the middle of triangle Siena-Arezzo-Firenze.The apartment has a double bedroom, a bathroom with showeran and an open kitchen/dining room with a double sofa bed. Direct access to a terrace equipped by the pool.  …see more

13 Photos

House | 1 Bedroom | sleeps 2

3 Nights min stay

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from £92 /night

£642 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Maria Luisa is a beautiful apartment furnished in a Tuscan style, decorated with quality furnishing and mere steps away from a marvelous swimming pool. Nestled in a park surrounded by cypress trees it offers a charming and relaxing holiday. On request, guests can have meals cooked for them by a private chef beside the pool.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £128 /night

£893 - £1751 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
High in the Vallombrosa Mountain range and overlooking the entire Val d'Arno that runs from Florence to Arezzo, Villa Treggiano has been the much loved holiday home of an Italian family living in Florence.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £332 /night

£2320 - £4160 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
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.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

4 Nights min stay

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from £389 /night

£2720 - £3600 / week

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Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
This imposing Leopoldine villa, with its pale cream external walls and typical rooftop dovecot, commands an exceptional position on an elevated, walled-in terrace, surrounded by mature trees and enjoying magnificent countryside views.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 7

7 Nights min stay

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from £136 /night

£951 - £1880 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £172 /night

£1200 - £2304 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Villa Il Palazzetto is an elegant 17th century villa built on the remains of the ancient castle of Monterchi, It is a perfect Tuscan holiday destination, situated in the small town of Monterchi but totally private due to the thick walls of the old castle.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £195 /night

£1361 - £1832 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
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.  …see more

22 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £343 /night

£2400 - £4000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Paradiso is a splendid villa situated in a strategic and panoramic position with stunning views over the open countryside. The villa has been constructed in two symmetrical wings, slightly curved to follow the longitudinal slope of the land.  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

Good 3.5/5 

7 Nights min stay

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from £129 /night

£900 - £1390 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Villa Montedoglio has been classified,by Tuscany Region, as "Residenza d'Epoca" which is equivalent to "National Trust" or "Heritage Grading".  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £400 /night

£2800 - £5600 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Magnifica is an old country residence, skilfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property.  …see more

23 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £268 /night

£1872 - £3280 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
This stunning 17 th century villa is the result of skilful architectural renovation work and has been exquisitely furnished in period style, with eye-catching touches of luxury in its Venetian glass chandeliers, gold-framed mirrors and brocade soft-furnishings.  …see more

24 Photos

Villa | 10 Bedrooms | sleeps 20

7 Nights min stay

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from £551 /night

£3852 - £5140 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Carpino is an exclusive elegant villa renovated from an old farmhouse and its two barns, now transformed into a luxury villa with two annexes where everything has been perfectly conceived to make your holidays just perfect.  …see more

24 Photos

Lodge | 1 Bedroom | sleeps 4

3 Nights min stay

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from £55 /night

£382 - £586 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Fattoria Borgonuovo - La Rosa Charming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m). The owners speak and understand fluent English.  …see more

24 Photos

Villa | 11 Bedrooms | sleeps 22

7 Nights min stay

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from £378 /night

£2640 - £6280 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Originally a country estate dating back to 1795, this superb Leopoldine villa blends outstanding elegance and comfort with traditional rustic features which reflect its long history.  …see more

22 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £360 /night

£2520 - £3600 / week

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Key info:

  • Nearest beach 135 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Ulivi was completely restored in the last years and whilst the exterior is very in keeping with the local architecture, the interiors are modern and comfortable with every thing new, fresh and carefully considered to provide you with a perfect holiday experience  …see more

23 Photos

Villa | 4 Bedrooms | sleeps 6

7 Nights min stay

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from £206 /night

£1440 - £1840 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Barbara is situated on the top of a hill kissed by the sun and caressed by the stars. Skilfully restored to keep its ancient charm untouched, it attracts with its solemn dignity and with marked environmental, landscaping.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £183 /night

£1280 - £3000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
A spacious traditional Tuscan farm house, bright and relaxed country living, Villa Sorbello is where you will find peace and tranquility.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £131 /night

£917 - £1954 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £183 /night

£1280 - £2000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful property carefully and completely renovated in the heart of the Chiana Valley just 9 km from the beautiful town of Cortona.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £146 /night

£1020 - £2007 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £227 /night

£1584 - £2320 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Villa Gloria is perfect for relaxed extended family groups or two families on holidays together. It is very well located for all important tourist destinations.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £186 /night

£1296 - £2240 / week

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Key info:

  • Nearest beach 135 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The setting of this villa is nothing short of spectacular, commanding unspoilt, panoramic views over the Chiana Valley and the hilltop town of Civitella from its privileged, elevated vantage-point on a wooded hillside.  …see more

24 Photos

Lodge | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £55 /night

£382 - £586 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Fattoria Borgonuovo - Il Geranio Charming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m). The owners speak and understand fluent English.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £355 /night

£2480 - £3184 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
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.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £132 /night

£924 - £2368 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Poggio del Gallo is a large modern villa which also integrates traditional Tuscan design features providing the maximum comfort. Its position is just extraordinary overlooking the valley where vineyards and olive groves spread out into infinity.  …see more

21 Photos

Villa | 10 Bedrooms | sleeps 18

7 Nights min stay

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from £365 /night

£2552 - £5700 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Set on a secluded hillside, enjoying panoramic views out towards Arezzo and the Apennine range beyond, this villa really has it all! In addition to the lovely pool, a tennis court, gym, rooftop-sunterrace and outdoor jacuzzi will help you keep fit, as well as unwind!  …see more

24 Photos

Farmhouse | 10 Bedrooms | sleeps 20

Excellent 5/5 

3 Nights min stay

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from £146 /night

£1018 - £1866 / week

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Late Deal: save up to €430 (approx. £344)

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
The elegant pool area is ideally located for all guests at the heart of lush garden, where re-establish the right contact with nature. Between a walk and a dip in the pool, you can abandon a complete relax and rediscover the real taste of welness.  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £40 /night

£275 - £539 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
* Luxury gated small development * Swimming Pool * BBQ * Piazza * Stunning Views * Parking and Garage * 2 Bicycles for guest use New apartment with private balcony, 2 double bedrooms, large living room, modern kitchen and log fire.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £73 /night

£505 / week

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Key info:

  • Nearest beach 100 km
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
Welcome to Casa Cappellino - a beautiful vacation home of your very own in Tuscany. Nestled in the Tuscan hills on 6 acres with ponds and vineyard, we're certain you will love your beautifully restored private Tuscan house (not apartment). Contact us for more reviews. Cappellino is located in the genuine, Italian countryside so that authentic Italian life can be experienced.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £43 /night

£297 / week

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Key info:

  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Tuscany Holiday House  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £70 /night

£484 - £755 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
The apartment is very suitable for families or groups of friends (4-6 people) who have a car and want to do a tour of Tuscany. We take care of our guests needs and help them to make their holidays unforgettable ! We wait for Your at Cappannelle Holiday House! The apartment is very suitable for families (4-6 people) who have a car and want to do a tour of Tuscany..  …see more

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Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £218 /night

£1520 - £3120 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Mondello is in the heart of Tuscany,surrounded by 7 thousand square metres of parkland,private pool with Jacuzzy, fabulous panoramic terrace, free Wi-fi, rooms with frescoes.If you are less than 8 persons: ask for a discount! Villa Mondello is in the Tuscan countryside,12 beds,5 bathrooms, jacuzzi,private pool and panoramic terrace.  …see more

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Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £100 /night

£699 - £1999 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful 800 year-old hilltop villa with stunning views , 4 bedrooms (sleeps 10) and private 12m x 6m pool. On border of Tuscany and Umbria, perfect for exploring local area. Fully restored, the house exudes character. ideal for large groups and families.  …see more