Castiglione Rentals

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2,362 Houses

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

Gaiole in Chianti villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 13

“Unforgettable Vacation!” My family and I (six of us) stayed at Le Pratola for a week in June. We had such a great time. The villa is beautiful and comfortable, and the views of the Tuscan hills are stunning. The team at Le Pratola is amazing. Laura, the cleaning lady, is a doll. The cooking class with Barbara is so much fun! Elena and Monica's (the personal chefs) meals are delicious. The villa is beautifully decorated and so comfortable. We all had the best vacation! We will definitely recommend the villa to family and friends. It was the best trip we've ever been on! We would like to thank the team at Le Pratola for making our vacation to Tuscany so special.

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Price per night from

$2,378

Villa Adinolfi - Your perfect Escape on the Como Lake area

Annone di Brianza villa

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 18

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Price per night from

$2,995

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Vernianello - Type B

Poggibonsi farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Housekeeping Included, Games room, Pool or snooker table, Swing set or jungle gym

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Price per night from

$204

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Housekeeping Included, Games room, Pool or snooker table, Swing set or jungle gym

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Price per night from

$121

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

Casa

Piana di Lucca farmhouse

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 1

3 of 4 match: Housekeeping Included, Games room, Pool or snooker table, Swing set or jungle gym

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Price per night from

$370

Relais Villa Bonini, La Merope

Massa b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$259

Ripostena 7-Trinciatoio

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

Ripostena 6-the dryer

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

Ripostena-5 The Remittance

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

Villa Colonica Tuori - Tuscany Farmhouse with Staff in Truffle Hunting Estate

San Piero A Sieve villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$3,081

Villa Giuliana, appartamento BILOCALE 4 Ptl, all'Isola d'Elba.

Capoliveri townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$68

Gardenpark Soleil Nebbiuno Lake Maggiore Villa 6 rooms

Fosseno villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 12

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$302

Antico Borgo Ripostena - 8 Casa Vecchia

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

Ripostena-Melissa House 1

Casole d'Elsa house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$1,233

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$99

Tenuta Contessa Chiara

Fontanile villa

  • 9 bedrooms
  • 15 bathrooms
  • sleeps 17

“Gail's review of Villa Cortese” Our experience at Villa Cortese was terrific. The owner is a great hostess and we felt very welcomed. The property is lovely and the region is our favorite.

Responds fast! avg. 1 hour 24 minutes

3 of 4 match: Housekeeping Included, Games room, Pool or snooker table, Swing set or jungle gym

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Price per night from

$1,479

Villa Le Panche, An 18th Century Bishop's Villa in a Lush Tuscan Valley

Pistoia villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

3 of 4 match: Housekeeping Included, Games room, Pool or snooker table, Swing set or jungle gym

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Price per night from

$529

3 of 4 match: Housekeeping Included, Games room, Pool or snooker table, Swing set or jungle gym

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Price per night from

$572

Casale del Lago

San Casciano in Val di Pesa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

3 of 4 match: Housekeeping Included, Games room, Pool or snooker table, Swing set or jungle gym

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Price per night from

$247

Villa Roncovisi

Monsummano Terme villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 19

3 of 4 match: Games room, Housekeeping Included, Pool or snooker table, Swing set or jungle gym

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Price per night from

$688

Poggio Rosemary - luxury farmhouse

Montespertoli farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 8

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$1,233

Villa Le Bolli: a vacation like at your home!

Radicondoli villa

  • 12 bedrooms
  • 14 bathrooms
  • sleeps 36

“A beautiful place to spend great moments with friends and family” We have been three families, a couple and some friends arriving on their own. It was one of the most relaxing, funny and wonderful holiday we have ever spent. The kids loved their time at the pool, the garden, with dart, billiard, ping-pong and table soccer and of course with the cat "Luigi". We adults had lots of time for chatting, laughing, joint cooking and eating, relaxing and some sports. The professional and big kitchen is a real asset. Albeit the nearby very fine and cosy restaurants, we usually preferred staying among us in the villa. Both, in sun shine and rain, the villa offers all you need for a great time in the big group (a big salon with open fire, several living and dining rooms indoor, the big and well-kept garden, main terrace, barbeque and pool outdoors). There are however also enough spaces to retire to, such as a hammock below a beautiful old oak, hidden benches in the garden, comfortable sofas here and there, and of course the spacious sleeping rooms, each with individual features and great views over the Tuscan landscape. We definitely can recommend this place!

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$1,972

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$2,113

Castello di Cabbiavoli

Castelfiorentino castle

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$1,405

Tenuta Le Selve

Toscolano-Maderno villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 18

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$2,736

LAKE COMO HISTORIC LUXURY VILLA- 1200M2 OF PURE SPLEDOUR

Como apartment

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 22

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$11,450

THE ITALIAN FAIRY TALE ON THE SHORES OF LAKE COMO- A MAGICAL 1300M2 HOME

Pigra apartment

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$7,901

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$2,061

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$6,902

Petrolo winery Villa. Events, weddings & large families. Service included

San Leolino villa

  • 16 bedrooms
  • 14 bathrooms
  • sleeps 33

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$1,972

Historic Villa

Toscolano-Maderno villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

3 of 4 match: Swing set or jungle gym, Games room, Housekeeping Included, Pool or snooker table

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Price per night from

$1,356

Chalet in Toscane aan zee te huur | Camping Paradiso in Viareggio | Italië

Viareggio chalet

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Pool or snooker table, Games room, Housekeeping Included, Swing set or jungle gym

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Price per night from

$81

the farmhouse is surrounded by the famigliaree environment

Ciliegi b&b

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 6

2 of 4 match: Games room, Swing set or jungle gym, Housekeeping Included, Pool or snooker table

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Tuscany Chalet in family camping by the sea, near Pisa and Lucca

Viareggio caravan/mobile home

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Housekeeping Included, Swing set or jungle gym, Games room, Pool or snooker table

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Price per night from

$35

Agriturismo Terra e Cielo

Serra Ricco farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Games room, Pool or snooker table, Housekeeping Included, Swing set or jungle gym

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Price per night from

$117

Viewing 38 of 2,362
rentals in Castiglione

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