Villas Castiglione del Lago

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565 villas

Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 58 minutes

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Price per night from

$1,031

Spacious Villa in Tranquil Setting with Solar Heated Pool, Views and Wifi

Citta di Castello villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

“Great holiday for everyone” We were a combination of three families, including grandparent, cousins, friends, including children from 9 - 23 and there was something for everyone. Lots of room for kids to run around in grounds, big pool with lots of chairs/lounges, great outdoor eating morning, noon and night, good kitchen, bedrooms and bathrooms in abundance. Ipod dock and books for everyone. We travelled as far as Rome, Perugia, Todi, Spoleto, etc. Highly recommended.

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Price per night from

$388

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Price per night from

$381

Luxury Country Villa in Val d'Orcia, close to Montepulciano and Pienza

Chianciano Terme villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$454

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$552

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

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Price per night from

$3,138

La Dimora Main Villa + 2 Cottages for 20

Sarteano villa

  • 9 bedrooms
  • 2 bathrooms
  • sleeps 20

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Price per night from

$3,497

Aiola

Sarteano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,660

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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Price per night from

$1,104

Tullia

Cortona villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$798

La Dimora Main Villa for 14 adults plus 2 children

Sarteano villa

  • 7 bedrooms
  • 11 bathrooms
  • sleeps 16

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Price per night from

$2,771

Tuscan private villa with large pool and garden

Chiusi villa

  • 12 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$665

Holiday Villa in Cortona

Cortona villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$687

Il Casale, Casa Nova

Spedalicchio villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 17

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Price per night from

$859

Villa San Martino

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$502

Stunning, luxury villa with large private pool

Piegaro villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$252

Villa Sant Antonio

Castiglion Fiorentino villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$386

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Price per night from

$381

Windmill

Cortona villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$491

villa ai cedri

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$404

Fonte al Vento:the Villa

Cortona villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$875

Villa L'Antica Vetreria

Piegaro villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$491

Villa Ivana - Exclusive Luxury Tuscan Villa in Cortona - Italy

Cortona villa

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 18

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Price per night from

$1,545

VILLA BIANCA LA LUNA

San Feliciano villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$1,052

Colognola, authentic hilltop villa overlooking Trasimeno Lake

Magione villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$1,341

Villa Biancaluna

San Feliciano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$701

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$781

Rural Tuscany | Panoramic luxury villa with pool

Sarteano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$2,147

Casa di Pan 6, Emma Villas

Panicale villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$372

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.

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Price per night from

$1,480

La Villetta di Dante 6, Emma Villas

Citta della Pieve villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$557

Villa Gaggioleto

Castiglion Fiorentino villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$351

Villa il Mandorlo

Passignano Sul Trasimeno villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$329

Villa San Francesco

Fratticciola villa

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 24

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Price per night from

$889

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Price per night from

$482

Villa Biancaluna

San Feliciano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$701

Casale Collina Verde - San Casciano Dei Bagni, Toscana

Casciano villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$1,985

Villa Il Granducato

Rigutino villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 19

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Price per night from

$536

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rentals in Castiglione del Lago

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