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382 Houses

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Match: Children's pool Private outdoor pool (unheated) City breaks

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Price per night from

$874

Holiday Villa in Cortona, La Fiorita

Cortona farmhouse

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 20

Match: Children's pool Private outdoor pool (unheated) City breaks

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Price per night from

$1,409

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Amazing villa for 8 ppl. with swimming-pool at Castiglion Fiorentino

Castiglion Fiorentino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 50 minutes

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$375

Casale Fontocchio with nice swimming pool

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 4

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$396

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$546

Villa Borgonuovo, marvelous example of the traditional tuscan farmhouse.

Cortona villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$396

Villa at the Foot of Cortona in Tuscany

Cortona villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

“Perfect accommodation for five couples and one baby” We wanted a large holiday accommodation which would provide 5 couples with the opportunity to enjoy a holiday together,but with no strangers, and also for each couple to be able to find their own space when they wanted.i pagliai was perfect.There was an excellent communal dining room and Vittorio and his staff went the extra mile to make our holday a real treat.

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$1,057

Villa Eugenio, authentic villa walk to village

Cortona villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 11

“Dream Vacation” It is s beautiful, private estate. You will need a car to get anywhere, but otherwise the location is ideal. Beautiful views, quiet. Sign up for a dinner to be fixed for you- it was amazing! We added a second dinner once we had the first! The women who cooked where sweet and friendly.

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$302

Villa Bianca

Cortona villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$326

Villa la Foce: breathtaking panoramic view

Castiglion Fiorentino villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“A little paradise” We enjoyed 3 wonderful weeks in a nearly perfect surrounding.

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$353

Villa Alma: the pool is a dream

Cortona villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“our vacation at Villa dei Ciliegi was a dream” we have spent 4 weeks at Villa dei Ciliegi. The house is made for a good size family with the open kitchen and the option to eat in and outside, the pool is simply a dream, the garden huge and meticulous maitained, the location on the hill provides privacy and a stunning view and Cortona and surroundings gave us lots of options to explore the tuscan charm. we loved it so much, we will be back next year.

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$1,487

The sun-view farmhouse is located in the green between Tuscany and Umbria

Mercatale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 51 minutes

2 of 3 match: City breaks, Children's pool, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$185

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 3 match: Private outdoor pool (unheated), City breaks, Children's pool

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Price per night from

$124

Villa La Pergola

Cortona villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$291

La Graziosa, graceful cottage with lovely pool.

Cortona villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Quiet beautiful place” We had an excellent holiday in this place. We will surely come back !

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Price per night from

$141

Valerie, luminous villa among rolling Tuscan hills

Cortona villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“A dear memory in Tuscany” Lost in a peaceful place on the slopes, this country is just a dream to care for ever. More than a comfortable home, this hideout is full of charming details and helpful amenities. Just take your time to sit out to see the wonderful views and take a bath in the pool, hearing the cicada enjoying the summer. A place full of poesy, it was a privilege to share for a week the house. Hope we can come back someday.

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$353

Holiday house-the House Cells-

Farinaio farmhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$345

Responds fast! avg. 2 hours 58 minutes

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$180

LE MURA ETRUSCHE

Cortona apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Villa con meravigliosa vista sul lago Trasimeno e grande piscina panoramica

Lisciano Niccone villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$880

Villa Church

La Dogana villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$336

Responds fast! avg. 2 hours 58 minutes

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$591

The window on Cortona

Cortona villa

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 52 minutes

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$284

CASOLARE IL CONDOTTIERO

Montecchio Vesponi house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

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Villa Il Casone

Montecchio villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 22

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$353

villa ai cedri

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$406

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$501

Casale Girifalco

Cortona villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$719

Sole - Agriturismo Marilena la Casella

Lisciano Niccone farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$40

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$501

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$308

Amazing villa 2 km away from the beach for 6 ppl. with swimming-pool

Tuoro sul Trasimeno villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 50 minutes

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$269

Villa Borgo delle Spighe- A nice country estate sets a wonderful scenery

Cignano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 19

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$874

Splendid Villa by Olive Groves and Vinyards at Fontocchio on Cortona

Cortona villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 17

“Heaven” Villa Fontocchio is a very special place to me. We stayed there for 5 weeks in 2006 and 3 weeks in 2008. It is an amazing property- there are 5 bedrooms and 5 bathrooms. It is extremely comfortable and the pool is great (which also has a pool house). There is also a very large outdoor table as well. The owners of the property are just wonderful people. Carlo made every effort to make sure that we were happy during both stays. The villa itself is at the foot of the hill to Cortona. It is well situated as there is a great grocery store very close by with charming Cortona at the top of the hill. There is a beautiful olive grove and vineyard behind the house as well. It is also very close to the train station I have so many wonderful memories of this place and I cannot recommend it more highly. I know I will go back to this place!

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$550

Orchidea - Two double bedroom # 6

Val di Chiana guest house

  • 13 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$272

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$161

Fonte al Vento:the Villa

Cortona villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$879

2 of 3 match: Children's pool, City breaks, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$353

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