Vacation Rentals & Villas in Grosseto

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244 Houses

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

Match: Heated pool

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Price per night from

$1,031

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 11 minutes

Match: Heated pool

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Price per night from

$111

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Heated pool

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Price per night from

$124

Villa Colle Tuscan Poolside House with Jacuzzi

Volterra house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Heated pool

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Price per night from

$370

Villa LA VALIANA (Montepulciano)

Montepulciano villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening sun sets over the gently rolling hills, relaxing in a chaise by the glistening pool, enjoying a café crème or glass of wine on the patio surrounded by roses, lemon trees and pots of flowers, or gazing beyond at Cortona high on a hill or Trasimeno Lake in the valley below, you will come to know this is a very special place. La Valiana is centrally located for explorations to nearby villages and wineries, Cortona, lovely Pienza (a favorite), Montepulciano or easy day trips to Montalcino, Orvieto, Siena, Arezzo, Florence, Chianti and beyond. It is comfortable and beautifully decorated in classic, Tuscan style with fine architectural details such as wrought iron arched windows, doors and Travertine marble floors. You will be well taken care of and looked after by Cecelia and her Family who are the most gracious hosts - they are dedicated to making your stay a wonderful, memorable one, making themselves available should you need any assistance. Their warm hospitality and attention to detail will make you feel special and, at once, a part of the family. If you opt to have a meal prepared and waiting for your arrival after a long day of travel or touring, it will not disappoint and, quite possibly, could be one of the best meals in all of Tuscany, especially when enjoyed under the stars. You will want for nothing - except perhaps to extend your stay, or at the very least, come back again! You can be sure we will be back!!

Match: Heated pool

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Price per night from

$739

Casale Santappiano

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

Match: Heated pool

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Price per night from

$555

Luxury Villa at Greve in Chianti

Greve in Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 9

Match: Heated pool

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Price per night from

$616

Farmhouse immersed in the woodland

Volterra house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$801

Casa il Mandorlo private garden - pool

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Match: Heated pool

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Price per night from

$136

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!

Match: Heated pool

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Price per night from

$1,232

Molino del Chianti

Bucine villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$792

Casale Etruria

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Heated pool

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Price per night from

$353

Casale i Gotti

Guardistallo villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$704

Villa Martina

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$1,584

Farm in Chianti

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Heated pool

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Price per night from

$770

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

Match: Heated pool

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Price per night from

$510

Castello del Granduca 20

Campiglia Marittima villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

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Price per night from

$2,094

Villa Stefano

Bibbiena villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 15

Match: Heated pool

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Price per night from

$423

Villa Pergine

Pergine Valdarno house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$566

Casale Kiss

Guardistallo villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$748

Villa Berta

Poppi villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Match: Heated pool

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Price per night from

$652

Villa in Chianti with heated swimming pool and A/C

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 19

Match: Heated pool

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Price per night from

$577

Match: Heated pool

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Price per night from

$909

Il Sasso Il Sasso

Chianciano Terme house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Heated pool

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Price per night from

$1,153

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.

Match: Heated pool

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Price per night from

$2,376

Villa Rinaldi

Sammontana villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Heated pool

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Price per night from

$1,056

Villa Cascine

Montaione villa

  • 17 bedrooms
  • 14 bathrooms
  • sleeps 29

Match: Heated pool

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Price per night from

$1,446

CASA FEBEA 6 people

Chiusi villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$210

4BR Tuscany’s sun-basked countryside

Montespertoli house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Heated pool

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Price per night from

$2,218

Villa i Prati

Montaione villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 22

Match: Heated pool

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Price per night from

$996

Villa Sarteano

Contignano villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

Match: Heated pool

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Price per night from

$1,943

Villa Lombards

Peccioli villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Heated pool

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Price per night from

$718

Il Felceto - luxury 6 BDA villa with heated pool

Citta della Pieve villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Heated pool

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Price per night from

$986

Podere il Sogno

Tavernelle villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$907

Villa Ciggiano

Castelfalfi villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$2,112

Villa Popillo

Montaione villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Heated pool

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Price per night from

$840

Villa in secluded grounds of 1 hectare

Gavorrano villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$247

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Heated pool

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Price per night from

$824

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