Castellina In Chianti Rentals

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Price per night from

$1,295

Great rentals within 20 miles that match your search

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

$2,371

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

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Price per night from

$1,229

la lodola

Crete Senesi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$148

Salve Regina

Chiesanuova barn

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$405

VILLA FLORENCE CASA SERENA

Montespertoli villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$521

VILLA POZZOLO Exclusive All-inclusive Charming family parties lovely weddings

Florence villa

  • 18 bedrooms
  • 16 bathrooms
  • sleeps 40

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Price per night from

$3,687

Villa rentals apartments 4 bed

Montespertoli villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$220

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$2,107

Casa Farsetti

Castelfiorentino villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$357

VILLA TALCIONA

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$191

TuscanFlat

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 7 minutes

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Price per night from

$172

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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Villa Chianti Furnace with pool and spa in Tavarnelle Val di Pesa!

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,668

Villa Parmolaia

Ville di Corsano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$1,931

Villa Florence - Casa Serena

Montespertoli villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$521

Villa Rinaldi

Sammontana villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,054

Luxury Villa Canova

Mercatale di Val di Pesa villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 16

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Price per night from

$4,953

Luxury Villa Pratomaggio

Radda in Chianti villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 10

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Price per night from

$2,752

Luxury Villa Faggeto

Siena villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 17

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Price per night from

$2,354

Luxury Villa Castelio

Radda in Chianti villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

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Price per night from

$4,799

Villa Reggello

Ruota villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$918

Villa Radda

Selvole villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$2,930

Villa Ripertoli luxury secluded family-owned farmhouse, Tuscany

Greve in Chianti villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 17

“Second visit as great as the first!” We have rented the Ripertoli property twice in the past three years. We spent a wonderful week there in 2010 and then two weeks in October of 2013. The location is exceptional, both for it's proximity to the heart of Chianti Classico, and for the sheer beauty of the area. Great cycling, hiking, and relaxing. As a professional caterer, I particularly enjoy the great availability of local foods and the well equipped kitchen that Deborah has put together. The home is large, plently of privacy as well as wonderful common area with a great kitchen and sitting area. The grounds are great as well. There are a plethora of great restaurants in the area, varying in price and style. Greve has plenty of local grocers including a wonderful local butcher shop run by Paulo and his mother, and a great green grocer as well as two bakeries, excellent gelato, and all of the other typical but essential shops.

Responds fast! avg. 1 hour 53 minutes

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Price per night from

$509

Casale Figlinelle

Gaiole in Chianti villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$1,545

Villa Perla- Homelike Villas

Cancelli villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$282

Villa Velari In Volterra With Private Pool, Ac - Villa Velari

Ulignano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$170

Villa il Vigneto- Homelike Villas

Panzano in Chianti house

  • 7 bedrooms
  • 11 bathrooms
  • sleeps 14

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Price per night from

$2,108

Villa nel Verde- Homelike Villas

Panzano in Chianti villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$1,195

Villa Terra di Siena- Homelike Villas

Panzano in Chianti villa

  • 18 bedrooms
  • 18 bathrooms
  • sleeps 36

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Price per night from

$5,408

Villa Chianti - Homelike Villas

Terranuova Bracciolini house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$576

Villa delle Torri - Homelike Villas

San Gimignano house

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 20

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Price per night from

$1,475

Villa il Giardino- Homelike Villas

Lucolena villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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Price per night from

$2,108

Villa Sempreverde- Homelike Villas

Panzano in Chianti house

  • 15 bedrooms
  • 16 bathrooms
  • sleeps 30

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Price per night from

$3,161

Villa Bellavista - Homelike Villas

Montegonzi house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$413

Villa la Corte-Villa with pool and tennis court in the Chianti countryside

San Donato in Poggio villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

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Price per night from

$1,266

Villa Poggio Cherici-With private pool in the Tuscan countryside, near Florence

Rignano sull'Arno villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$1,120

VILLA BELSOLE

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

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Price per night from

$639

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rentals in Castellina In Chianti

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