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346 Holiday homes in Cortona

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346 Results  |  
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
  • Great for children of all ages 5
  • 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

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
  • 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

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

Featured properties

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

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 | 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

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
  • 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

17 Photos

Apartment | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £49 /night

£340 - £424 / week

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Key info:

  • Great for children of all ages 5
  • No pets allowed
Elegantly furnished apartment a few meters away from the main sites of the city At 50 meters from the apartment you will find the public parking where you can leave your car.  …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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

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 children over
  • Car advised
  • Some pets are welcome - please contact the owner
  • 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

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:

  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • 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

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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

16 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £157 /night

£1094 - £1824 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

13 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £49 /night

£340 - £509 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
From the town of Cortona and 'possible in the day, to reach the most beautiful art cities of central Italy from Florence to Rome and 18 km Lake Trasimeno.Included you will find a set that includes: basic necessities (coffee, tea, seasoning, salt, sugar, detergents...... Ideally located, very quiet. Discount depending on length of stay.completely renovated, nice furnishings.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

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from £37 /night

£255 - £340 / week

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Key info:

  • Great for children of all ages 5
  • Pets welcome
L'Etrusca e' un alloggio perfetto per chi vuole trascorrere le sue vacanze nel cuore della citta' e vivere direttamente la nostra tradizione Near of the most important Tuscany and umbria Town like: Firenze, Arezzo, Montepulciano, Pienza, Montalcino,  …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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • 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

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
  • Great for children of all ages 5
  • 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:

  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
For those who enjoy privacy, this beautifully restored traditional Tuscan farm house offers the opportunity experience real Tuscan living.  …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
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • 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

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
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • 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

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
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

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
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

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
  • Great for children of all ages 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The Villa is set along a sun soaked hill where the garden extends into pretty olive groves and vineyards.  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

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from £334 /night

£2332 - £3392 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Martino offers not just another holiday in Tuscany or Umbria; this is a really special place. The villa is beautifully presented and has an exquisite pool with spectacular views across the famous Niccone Valley towards Mercatale di Cortona. Only 15 minutes from the villa you can easily access the Etruscan town of Cortona.  …see more

23 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
  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
Swimming pool, beach or lakeside relaxation, air conditioning, car essential, may take pets - please enquire, Cortona, panoramic  …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

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:

  • Great for children of all ages 5
  • 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

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

4 Nights min stay

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from £55 /night

£382 - £509 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
Delightful spacious self catering apartment in beautifully restored 18th century Tuscan farmhouse with pool. Rural, quiet & relaxing yet close to the charming Etruscan town of Cortona & within easy reach of the major art & cultural centres of Tuscany & Umbria. Perfect for art, architecture, wine, fine cuisine, scenery, walking, cycling and simply relaxing.  …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 5
  • 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

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
  • Great for children of all ages 5
  • 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

24 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £58 /night

£403 - £530 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
Spacious, comfortable self-catering apartment in beautifully restored 18th century Tuscan farmhouse with pool. Rural, quiet and relaxing yet close to the charming Etruscan town of Cortona and within easy reach of the major art & cultural centres of Tuscany & Umbria. Perfect for art, architecture, wine, fine cuisine, scenery, walking, cycling and simply relaxing.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £73 /night

£505 - £848 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 118 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
Charming, comfortable self catering apartment in our charmingly restored 18th century Tuscan farmhouse with pool Rural, quiet and relaxing, yet close to the delightful Etruscan town of Cortona & within easy reach of the major art & cultural centres of Tuscany & Umbria. Perfect for art, architecture, wine, fine cuisine, scenery, walking, cycling and simply relaxing.  …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
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
Charming villa with private pool near Cortona and lake Trasimeno  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £47 /night

£328 - £496 / week

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Key info:

  • Great for children of all ages 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Stunning breath taking view of the Val di Chiana Valley from the living room and kitchen windows!! It'll be printed in your memory for ever! Walking distance from the main square and all the fabulous restaurants and shops.  …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

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £134 /night

£936 - £2912 / 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
Characteristic farmhouse near Cortona in Tuscany immersed in large private gardens, situated at the foot of the ancient town of Cortona.  …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
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Family- friendly 3 bedroom restored Farmhouse with private pool, just below Cortona  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £104 /night

£728 - £1300 / week

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Key info:

  • Nearest beach 35 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Splendid Tuscany cottage in a picturesque and peaceful spot in the mountains above Cortona.  …see more

22 Photos

Villa | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £194 /night

£1352 - £3224 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Stunning villa in an extremely panoramic position in the vicinity of Cortona.  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

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from £35 /night

£240 - £320 / week

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Key info:

  • Great for children of all ages 5
  • Pets welcome
Apartment / Condo in Cortona with 1 bedrooms sleeps 3  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £246 /night

£1716 - £3088 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 8  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 3

3 Nights min stay

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from £93 /night

£648 / week

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Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
Apartment / Condo in Cortona with 2 bedrooms sleeps 3  …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
  • Great for children of all ages 5
  • 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

11 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £75 /night

£520 / week

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Key info:

  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Apartment / Condo in Cortona with 2 bedrooms sleeps 4  …see more