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351 Holiday homes in Cortona

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351 Results  |  
14 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £61 /night

£424 - £662 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Apartment for a couple or a family with one or two children in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area. The kitchen is fully equipped and big and lighting bedroom have en-suite bathroom.  …see more

22 Photos

Farmhouse | 12 Bedrooms | sleeps 24

2 Nights min stay

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from £340 /night

£2375 - £5088 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Villa Cuiano is a sprawling farmhouse with marvelous panoramic views of the Niccone Valley and the mountains of Umbria. The farmhouse has been divided in self-cointained apartments, that possible to rent separated too. Four fireplaces in flats and pizza oven outdoor. Villa with Pool, Terrace, Cook service, Playground, BBQ: sleeps 2 to 24 in 6 flat renting separated too.  …see more

17 Photos

Farmhouse | 3 Bedrooms | sleeps 4

2 Nights min stay

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from £102 /night

£713 - £933 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Casa Luca country house with fireplace, two balcony, fully equipeed kitchen, TV SAT, Wi-Fi, CD Stereo, 2 bedrooms and 1 bathroom, perfect for a family with 2 or 3 or 4 children. Casa Luca has also a mansard bedroom suitable for other 2 children.  …see more

Featured properties

12 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £77 /night

£535 - £933 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Flat for 4 people with outdoor patio in a villa with swimming pool, large garden, bbq, garden furniture and baby playground area. It is perfect for wheel-chairs users. The kitchen is fully equipped and there is a dishwasher and a fireplace. La Stalla has also a tipical tuscany stone fireplace fantastic to relax in front of there during the winter.  …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
  • Suitable for children of all ages
  • 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

22 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £61 /night

£423 - £603 / week

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Key info:

  • Nearest beach 165 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
The apartment Angelo is part of a larger building once an ancient mill which has been carefully restored to the highest standards and transformed into a country residence with 30 apartments enjoying stunning views, immersed in a green setting only 3 km from Cortona.  …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:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

23 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £332 /night

£2320 - £3680 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • 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 | 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
  • Suitable for children of all ages
  • 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

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
  • Suitable for children of all ages
  • 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

23 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £195 /night

£1361 - £1649 / week

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Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

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
  • Suitable for children of all ages
  • 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

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
  • May take pets – please enquire
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

7 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £742 /night

£5194 - £6233 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Private Villa in Cortona Area, Near Montepulciano, Tuscany, Italy. Private Swimming Pool, sleeps 18. Beautiful gardens, green grass all year. Multiple family accommodation. Broadband, TV, DVD, iPod docks, table-tennis, bikes.  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 5

Very Good 4/5 

7 Nights min stay

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from £85 /night

£590 - £990 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
700 years ago, San Silvestro was a little church - now it's a charming rental villa and excellent value too!  …see more

12 Photos

Villa | 4 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £136 /night

£950 - £1590 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This unpretentious, large house has the authentic flavour of times past and glorious views up to Cortona. The pool was built in 2008 with safety in mind: it's 3 ft 9 ins deep and completely fenced for total peace of mind.  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 2

Very Good 4.5/5 

5 Nights min stay

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from £50 /night

£350 / week

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Key info:

  • Nearest beach 7 km
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
Fifteen minutes walk to Cortona on a private path with exceptional views, the stone-house is secluded, and restored and furnished with taste. Surrounded by garden terraces on various levels, and well provided with garden furniture for outdoor meals and relaxation. SEPTEMBER OFFER: £250 for 5 or 7 nights. Gourmet-meals under request.  …see more

10 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £364 /night

£2544 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa il Pino is an old farmhouse carefully restored while maintaining the aesthetic standards of the old Tuscan farmhouses using the original materials, such as roofing tiles, the handmade terracotta tiles for the floors, doors and windows all handcrafted in solid che  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £285 /night

£1992 - £2360 / week

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Key info:

  • Nearest beach 26 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
The Villa is set along a sun soaked hill where the garden extends into pretty olive groves and vineyards.  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £171 /night

£1192 - £1320 / week

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Key info:

  • Nearest beach 25 km
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Coppa di Sopra is an elegant and enchanting villa overlooking one of Tuscany's favorite valleys - “Coppa di Sopra is a magical place.  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £67 /night

£464 - £560 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Apartment Roland is a fun and stylish and inexpensive home set in the foothills of Cortona are two individual and lovely properties with spacious gardens, magnificent private pool, tennis court and many wonderful features.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

7 Nights min stay

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from £166 /night

£1156 - £2260 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
For those who enjoy privacy, this beautifully restored traditional Tuscan farm house offers the opportunity experience real Tuscan living.  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £90 /night

£624 - £664 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa August' provides a good value family holiday in Tuscany, Cortona. With its huge swimming pool, tennis court, barbecues and lots of space both inside and out, this is a perfect for young/teenage families to enjoy the area.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £138 /night

£960 - £1640 / week

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Key info:

  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
exceptional, Good value. Villa Sonia ioffers a fabulous Tuscan home for two to 14 guests! Fantastic views, Private Pool, Tranquility, Relaxation and much more.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

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from £96 /night

£672 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Casa Astrale is a lovely apartment providing a perfect base to explore southern Tuscany and Umbria. With its exclusive pool, very large gardens and , the ability to walk or cycle along the lake Trasimeno -  …see more

21 Photos

Villa | 1 Bedroom | sleeps 2

Excellent 5/5 

7 Nights min stay

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from £115 /night

£799 - £1051 / week

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Key info:

  • Nearest beach 14 km
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Why have so many people fallen in love with the charm of Cortona? Although the central area of this lovely and ancient city is well known to many, there remains the secret and ever-so-charming quarter where this hidden gem will inspire and charm you.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £79 /night

£552 - £1016 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
"Perfect for half terms holidays - without any increase in the general rate" . 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.  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 7

Excellent 5/5 

7 Nights min stay

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from £229 /night

£1602 - £2139 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This is a place to enjoy an authentic Tuscan experience. Close to the historic town of Cortona and set in acres of olives and pastures - this beautiful 17th century newly renovated Mill House with private pool has been painstakingly restored.  …see more

15 Photos

Apartment | 4 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £125 /night

£872 / week

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Key info:

  • Suitable for children of all ages
  • No pets allowed
This lovely apartment is available for a minimum of 4 nights. A perfect location in the heart of Cortona and, a great base to explore many of Tuscany's and Umbria's famous towns, vineyards and stunning countryside.  …see more

15 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £98 /night

£680 - £1480 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Independent stone house close to Cortona, a former middle age tower with terracotta floors and gothic windows. 8 sleeps, swimming pool  …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
  • Suitable for children of all ages
  • 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

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
  • Suitable 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

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £152 /night

£1060 - £1272 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Family- friendly 3 bedroom restored Farmhouse with private pool, just below Cortona  …see more

20 Photos

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
  • Suitable 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

21 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £98 /night

£680 - £1400 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

24 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £119 /night

£827 - £1516 / week

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Key info:

  • Nearest beach 22 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £195 /night

£1360 - £2760 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Suitable 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

10 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £49 /night

£340 - £509 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Holiday apartment 2 km from Cortona in the country, equipped with every comfort ,silent An excellent base for excursions nearby (Lake Trasimeno, Montepulciano, Pienza, Siena, Gubbio, etc..), from the house you can also put your shoes on and go for a walk in the woods  …see more

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

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from £134 /night

£933 - £1272 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Nestled in the foothills of Cortona, overlooking the Val di Chiana and Mount Amiata. The perfect base for exploring the beautiful regions of Tuscany and Umbria or simply relaxing, surrounded by nature.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 15

7 Nights min stay

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from £286 /night

£2000 - £2800 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £63 /night

£440 - £624 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
"Il Villino di Cortona", is a cozy house nestled in the heart of val di chiana: in an area rich in history and cultural attractions. Tuscany holiday house. (exclusive use property, house, pool, garden). The veranda is ideal to enjoy a rich and tasty breakfast, or to immerse yourself in the reading a good book.  …see more

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
  • Suitable for children of all ages
  • 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

6 Photos

Guest house | 6 Bedrooms | sleeps 25

1 night min stay

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from £78 /night

£543 - £848 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • 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

14 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £71 /night

£495 - £950 / week

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Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
On the Tuscany/Umbria border, near Cortona and Lake Trasimeno, Castagnolo is one of 3 beautifully restored apartments. In the garden is a luxurious pool with jacuzzi attached . Walk across the field to the old market town of Mercatale. Private terrace. Wonderful views  …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
  • Suitable 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

17 Photos

Villa | 2 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

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from £73 /night

£509 - £806 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
Swimming pool, beach or lakeside relaxation, air conditioning, car essential, may take pets - please enquire, Cortona, panoramic  …see more

13 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £159 /night

£1113 - £1272 / week

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Key info:

  • Suitable for over 5s only
  • Car advised
  • May take pets – please enquire
  • Private garden
Peaceful villa in Tuscany, between olives and cypress . Close to many famous destinations in Tuscany and Umbria but you need a car. Relax, private garden, ideal if you like to live close to nature Villa in Tuscany, between olives and cypress , ideal if you like to be close to nature. Peaceful and relax  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £296 /night

£2068 - £3180 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A typical Tuscan house in bricks, with a garden, fruit trees, flowering trees, cypresses and rosemary bushes, a beautiful swimming pool is in the centre of the garden  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £103 /night

£720 - £2000 / week

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Key info:

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

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Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £134 /night

£936 - £2912 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Characteristic farmhouse near Cortona in Tuscany immersed in large private gardens, situated at the foot of the ancient town of Cortona.  …see more