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116 Holiday homes in Cortona

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116 Results  |  
21 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £98 /night

£686 - £1412 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A tranquil haven in which to recharge your batteries. Poolside relaxation with cultural visits. Great hill walking at the summit of Tuscany's toughest cycling hill climb. All this from our family friendly cottage-style apartment set high above the Tiber valley. Good sightseeing and great restaurants at nearby Cortona. An hour's drive from Perugia, Arezzo and Assisi.  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £86 /night

£599 - £1283 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • 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

20 Photos

Villa | 5 Bedrooms | sleeps 15

5 Nights min stay

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from £289 /night

£2017 - £2823 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Luxurious detached villa with private pool in southern Tuscany near Cortona. Panoramic and quiet location. 5 bedrooms, 11 bed places + 2 double sofa beds. Air conditioning and Wi-fi internet connection.  …see more

Featured properties

21 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £90 /night

£629 - £830 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Charming small villa near Cortona, large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. The perfect base to explore Tuscany and Umbria. Very comfortable, fully equipped. Stunning countryside. Free GPS, Italian cell phone,laptop. Swimming pools/thermal spas. Great restaurants. Short walk to village.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £35 /night

£244 - £377 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
La splendida vista della dolce collina cortonese, il tranquillo parco e la quiete della campagna della Val di Chiana vi permetteranno di apprezzare l'armonia del vostro “nido” di vacanza. Il nido è, per noi, simbolo di dimora accogliente.  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £35 /night

£244 - £377 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
La sua posizione strategica permette agli ospiti di assaporare appieno la tranquillità della vita di campagna e di raggiungere facilmente centri storici ed artistici dell'Italia centrale. “I Nidi di Cortona” è punto di partenza ideale per escursioni.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £93 /night

£649 - £2199 / week

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Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • 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

22 Photos

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

2 Nights min stay

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from £35 /night

£244 - £377 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
La villa di campagna “I Nidi di Cortona” è situata in campagna, presso il piccolo borgo rurale di San Marco in Villa (sec. XIV), ai piedi della collina su cui si distende la cittadina etrusca di Cortona.  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £572 /night

£4000 - £6775 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Restored to high standard. Accommodation split in two private buildings. Ideal location between South Tuscany and Umbria. Private tennis court.  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £158 /night

£1103 - £1838 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
3 bedrooms Tuscan country villa in panoramic location with private swimming pool , private garden and parking . Five minutes away from the beautiful medieval city of Cortona and the famous cooking school I Gustasapori  …see more

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1371 - £2783 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This charming Tuscan Farmhouse with a new salt water pool is ideal for family holidays as it is tucked away in a large garden in lovely, unspoilt Southern Tuscany near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £105 /night

£730 - £1256 / week

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Key info:

  • Great for children of all ages
  • 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

22 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

1 night min stay

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from £202 /night

£1412 - £2259 / week

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Key info:

  • Nearest beach 180 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a old village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome. 30 minutes from the highway and 10 from the train station.  …see more

23 Photos

Villa | 10 Bedrooms | sleeps 20

1 night min stay

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from £553 /night

£3871 - £5184 / week

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Key info:

  • Nearest beach 2 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Villa Under the Tuscan Sun walk to Town of Cortona. Amaziong view, beautiful swimming pool and tennis Court for exclusive use.  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 17

4 Nights min stay

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from £489 /night

£3420 - £4275 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The property Villa il Trebbio is an antique palace close to Cortona which dates back to the 16th century. The farmhouse in stone has been personally furnished by the owner with antique family pieces and reflects a simple and at the same time elegant atmosphere  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

1 night min stay

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from £277 /night

£1936 - £2541 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Recently restored Tuscan Villa with traditional Terracotta tiled floors, plunged in the greenery of southern Tuscany.  …see more

12 Photos

Cottage | 5 Bedrooms | sleeps 10

1 night min stay

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from £173 /night

£1210 - £2017 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Stone cottage in a wonderful hilly position, just a few minutes from the medieval town of Cortona. Gorgeous panoramic view from the private pool, and beautiful walks to explore including the ancient Roman road. Dip into the magical peace of the Tuscan countryside.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

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from £173 /night

£1210 - £2541 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
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.  …see more

13 Photos

Cottage | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £64 /night

£444 - £686 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Stone cottage in a wonderful hilly position, just a few minutes from the medieval town of Cortona. Gorgeous panoramic view from the private pool, and beautiful walks to explore including the ancient Roman road. Dip into the magical peace of the Tuscan countryside.  …see more

21 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4/5 

2 Nights min stay

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from £99 /night

£693 - £1155 / week

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Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • 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

26 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £207 /night

£1449 - £2390 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The location is vry convenient to visit many of the most beautiful location of central Italy, Tuscany and Umbria, still stayng in a relaxing and peaceful country place.Cortona, the awesom art city, made famous also from teh movie "under the Tuscan Sun" is very close  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

2 Nights min stay

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from £44 /night

£307 - £513 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Seni detached apartment of an ancient tuscan country house, private garden in a small country village near by Corotna, the famous meieval town. Swimming pool and traditional tuscan food lessons available  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £181 /night

£1265 - £2530 / week

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Key info:

  • Nearest beach 190 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Attractive holiday house for 10 persons, with swimming pool , in Arezzo  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £60 /night

£414 - £608 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Cortona  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £493 /night

£3445 - £4550 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden

Cortona Tuscan Villa with pool- rural views and two independent annexes within walking distance of the medieval walled town of Cortona.

 …see more

14 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £160 /night

£1120 - £1600 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Pets welcome
  • Private garden

Tucked away in the blissful rolling countryside on the edge of Cortona, this stone cottage with its private pool is a delightful hideaway for a coupleseeking to experience the best of Tuscany and Umbria.

 …see more

15 Photos

Guest house | 2 Bedrooms | sleeps 3

3 Nights min stay

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from £59 /night

£411 - £684 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
This place and the atmosphere will be the ideal ingredients to spend a peaceful and relaxing holiday immersed in the Tuscan countryside and at the same time to visit the most beautiful cities of historical and cultural interest and gastronomic center of Italy.  …see more

17 Photos

Apartment | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £66 /night

£462 - £770 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
This place and the atmosphere will be the ideal ingredients to spend a peaceful and relaxing holiday immersed in the Tuscan countryside and at the same time to visit the most beautiful cities of historical and cultural interest and gastronomic center of Italy.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £55 /night

£385 - £770 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
around the Villa La Fontana: The Parco del Trasimeno runs along the perimeter of Trasimeno lake and is the largest regional park in Umbria. The park includes three islands: the largest is Polvese Island, which is under the control of the Province of Perugia. Stunning Luxury villa in walking distance from Cortona  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 2

7 Nights min stay

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from £37 /night

£257 - £513 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa La Fontana is at the heart of prestigious places of historical interest and artistic national and world: ROME, the capital city with all its historical and architectural merit is about u'ora machine, FLORENCE, capital of the Renaissance is about an hour's journey. CORTONA is located just 15 minutes, ORVIETO 30 minutes, 40 min. SIENA, PERUGIA 20 min., Assisi 30 min.  …see more

24 Photos

B&B | 2 Bedrooms | sleeps 7

Very Good 4.5/5 

1 night min stay

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from £55 /night

£385 - £556 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
Casa in campagna; Vacanze; Toscana; Cortona; Relax; Piscina; Agriturismo; Firenze; Siena; Umbria; Lago Trasimeno; Montepulciano; Pienza; Assisi; Valdichiana; Valdorcia; bed and breakfast; La struttura è situata a poche centinaia di metri dall'uscita della superstrada e 8 km da Cortona.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £277 /night

£1936 - £2517 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Bella is a stunning, luxury villa nestled in the Valdichiana valley just a few kilometres from Cortona. An ideal destination for exploring the beautiful regions of Tuscany and Umbria.  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £110 /night

£764 - £1516 / week

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Key info:

  • Nearest beach 22 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Charming stone farmhouse with original features. Perfect for family holidays. Private pool, table tennis and Wifi Internet. Beautiful countryside views. Only 2 kilometres from a village with shops and restaurant. Sought after location on the Tuscany-Umbria border.  …see more

24 Photos

Lodge | 1 Bedroom | sleeps 4

2 Nights min stay

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from £55 /night

£385 - £590 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • 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 | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £104 /night

£726 - £2017 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming villa with private pool near Cortona and lake Trasimeno  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £52 /night

£363 - £638 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Beautifulapartment with swimming pool situated in the vicinity of Cortona, Tuscany.  …see more

22 Photos

Villa | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £195 /night

£1363 - £1678 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Stunning villa in an extremely panoramic position in the vicinity of Cortona.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £105 /night

£734 - £1311 / week

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Key info:

  • Nearest beach 35 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Splendid Tuscany cottage in a picturesque and peaceful spot in the mountains above Cortona.  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 16

2 Nights min stay

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from £55 /night

£385 - £1881 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Novole is a group of houses nestled in the green hills on the border between Umbria and Tuscany Novole offers easy access to the nearby towns of Arezzo, Siena, Florence, Montepulciano, San Gimignano and Perugia, and it is only 15 km away from Lake Trasimeno.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £71 /night

£495 - £1050 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
On the Tuscany / Umbria border, the old farm of Azienda Pilari is only a short drive to Cortona and Lake Trasimeno. A walk across the field takes you to an old market town with a few shops, bars and restaurants Wine and olive oil produced on the farm are available for purchase.  …see more

6 Photos

Guest house | 6 Bedrooms | sleeps 25

1 night min stay

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from £79 /night

£548 - £855 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
La Fiorita is a farmhouse nestled in the beautiful Tuscan countryside, on the border between the provinces of Arezzo and Siena.  …see more

15 Photos

B&B | 11 Bedrooms | sleeps 20

Min stay varies

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from £52 /night

£360 - £5984 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
bed and breakfast in toscana ,cortona ,casa vacanze ,piscina ,swimming pool ,restaurant ,ristorante ,mezza pensione ,giardino ,campagna toscana ,Montepulciano ,siena ,firenze ,arezzo ,perugia ,strada del vino ,wineries , medieval town , Il Sole del Sodo nel suo insieme, e nella semplice eleganza dei suoi dettagli, è la casa ideale per chi sceg  …see more

13 Photos

Finca | 11 Bedrooms | sleeps 24

Min stay varies

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from £367 /night

£2565 - £3420 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Casale toscano con piscina. Ampi appartamenti di lusso con aria condizionata . Viene affittato in esclusiva . Vicino all'autostrada ma immerso nella pace e silenzio della campagna toscana .  …see more

19 Photos

House | 1 Bedroom | sleeps 3

Min stay varies

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from £60 /night

£419 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Appartamento in agriturismo: casa unica appena ristrutturata con comodi servizi, immersa nel parco e adiacente alla piscina. ortaggi, olio extra vergine e vinsanto di produzione della casa  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £196 /night

£1368 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Ground floor 157 sqm suite with private terrace view to Cortona hill town, excellent point for day tours, near many cities in Tuscany and Umbria, such as Montepulciano, Arezzo, Assisi,Siena, Florence. great events during summer time, and many activities for the family. Stay in Tuscany with Activities at the Apartment Hotel La Mucchia  …see more

24 Photos

Villa | 10 Bedrooms | sleeps 20

Min stay varies

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from £785 /night

£5495 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Raggiungibile a piedi da Cortona. Villa per affitto settimanale a Cortona in Toscana con campo da tennis privato e piscina privata Speciale Villa a Cortona per matrimoni. Villa in Toscana per riunioni di Famiglia. Villa walking distance da cortona Piscina privata Campo da tennis privato Distanza a piedi da Cortona  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 4

Min stay varies

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Pricing unknown

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
'Vecchio Frantoio' is only a five minute drive from the medieval hilltop town of Cortona. The main A1 motorway is a fifteen minute drive from the apartment and the mainline train station is only a five minute drive away.  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

Min stay varies

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from £55 /night

£385 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Casa singola appena ristrutturata, conservando le caratteristiche della casa toscana; pavimenti in cotto, soffitti con travi in legno e mattoni a vista, ampio parco fruibile con attrezzature da giardino, piscina adatta a bambini. disponibile lettino bebè; bici gratis  …see more

9 Photos

Hotel apartment | 28 Bedrooms | sleeps 2

1 night min stay

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from £91 /night

£635 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Su una terrazza naturale, dalla quale si può ammirare un meraviglioso panorama della Val di Chiana, si trova una bellissima piscina circondata da un'area tenuta a prato attrezzata con sedie, lettini e ombrelloni. La piscina è aperta da Maggio a Settembre.  …see more

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House | 3 Bedrooms | sleeps 6

Excellent 5/5 

Min stay varies

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from £123 /night

£855 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
-  …see more