Oliveto Rentals

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Big garden,own pool and wheelchairfriendly, pets

Oliveto house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$480

Casale Irina by VacaVilla

Oliveto villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

Great rentals within 20 miles that match your search

IL CASALE TOSCANO

Cortona house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 10

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Price per night from

$615

Villa Merelli

Alberoro villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$211

Holiday House Le Corniole

Civitella in Val di Chiana villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$246

Podere Sant'Egidio

Castel Focognano villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 23

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Price per night from

$791

UNA VACANZA DA SOGNO

Gaiole in Chianti house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 1 minutes

Match: Private pool

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Price per night from

$271

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$770

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Price per night from

$499

Villa Portoverde Rental with Pool Jacuzzi and Sauna

Foiano Della Chiana villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$576

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Price per night from

$1,434

House in Tuscany with private infinity pool

Civitella in Val di Chiana house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$369

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Price per night from

$516

Pietra E Mattoni Nel Cuore Del Chianti

Loro Ciuffenna villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$738

Villa Arianna - 3 bdr-villa over the Trasimeno Lake!

Cortona villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$1,022

Casale Girifalco

Cortona villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$717

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: Private pool

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Price per night from

$738

Chianti Luxury Suite, Boutique Rental, Radda in Chianti - Siena

Radda in Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Dreams do come true in Radda” We spent a month in Europe and Radda was the last leg of our journey and the absolute best part of our trip. Besides the breath taking vistas that abound in all directions, the accommodations are spectacular. A comfortable bed, a gorgeous bathroom and a quaint sitting area with sink and fridge. Evenings we would enjoy a glass of wine on the terrace overlooking the orchard. The gardens are filled with rows and rows of lavender. Exquisite! The entire villa is like a setting from a romantic movie about Italy. To be really decadent, we had a massage poolside that Mila arranged for us. It was heaven. It really is a place to find peace and tranquility, away from the noise of life. Mila is a charming hostess and a fountain of knowledge re the neighboring villages and history. She was fascinating to listen to and not the least bit intrusive. If we needed her she was there, otherwise she respected our privacy. My one wish would be, to have the opportunity to return again to this paradise. Thank you Mila for a wonderful experience in Chianti.

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Price per night from

$332

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: Private pool

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Price per night from

$2,371

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$669

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$702

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

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Price per night from

$183

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Price per night from

$391

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Price per night from

$214

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Price per night from

$634

IL BORGO DI GEBBIA B & B Holiday House

Civitella in Val di Chiana b&b

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$308

Agriturismo Il Torrino

Cortona villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$509

Agriturismo L'Olivo

Serre di Rapolano cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 1 hour 11 minutes

Match: Private pool

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Price per night from

$111

Villa near Florence WiFi / Pool / Amphitheatre

Tuscany villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

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Price per night from

$1,322

Villa Magnolia

Teverina villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$474

Villa Ginestra

Teverina villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$359

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Price per night from

$187

Agriturismo Villa Panorama - 8 posti letto - Villa esclusiva - Siena

Rigaiolo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$590

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$1,229

A HOLIDAY IN THE HEART OF CHIANTI

Gaiole in Chianti villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 1 minutes

Match: Private pool

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Price per night from

$271

morandi mill old mill with private pool

Loro Ciuffenna watermill

  • 6 bedrooms
  • 16 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$746

Enchanting country house (12 + 4) with private pool

Lucignano b&b

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 31 minutes

Match: Private pool

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Price per night from

$290

Viewing 38 of 665
rentals in Oliveto

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