Province of Siena Rentals

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1,144 Houses

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$186

Beautiful Independent Tuscan Cottage For 2 With Spectacular Views

San Casciano dei Bagni cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Views amazing, house beautiful and Village so friendly” We stayed for one week at La Ginestra and could have been there for so much longer. We loved it, the view across the valley is a wow and the house is so tastefully decorated and of high quality. The village is just two minutes walk away and has a fab pub and lovely restaurants. I am a Food Technologist so food is very important to me - the butchers in the old town was fab, sausages and ham just so delicious. We really did feel accepted everyone was just so friendly to us. We toured most days and saw some beautiful Tuscan towns. We loved everything about it. Bed so comfy and beautiful, bedding crisp and white.

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Price per night from

$216

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.

Match: Garden

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Price per night from

$334

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

$1,033

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$230

Cesira Palazzina

Val d'Orcia b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$192

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$230

Podere Lucignano Secondo - Apt. La Mangiatoia (ground floor)

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$296

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$617

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A Slice of Paradise” We stayed at Podere Patrignone for 5 days in September. It was wonderful to stay in a self contained apartment after 4 weeks of hotels in France. The farmhouse is charming, the apartments are unique and quaint, the countryside was picture perfect and the weather was unseasonably warm. Simon and Verity were such hospitable hosts, yet give the guests their own space. We thoroughly enjoyed the weekly meal Verity and Pam created for all the guests. You must have a car to truely experience all the hidden charms of Tuscany, and everything is so close and the quality of food and wine was impressive. Our favourite memory of staying at Podere Patrignone was sharing sunsets on the terrace with other guests and partaking of good wine, great conversation and so many laughs. We will be back for another slice of paradise.

Match: Garden

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Price per night from

$186

Private Elegant Zen Cottage in Siena Tuscany

Torri cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$136

L'Olivo Gina, Minnie's Cottage: Your home in Tuscany, the land of Brunello

Montalcino house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$173

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 2 hours 23 minutes

Match: Garden

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Price per night from

$115

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$151

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: Garden

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Price per night from

$741

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Garden

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Price per night from

$770

4 bedrooms in a tower, home of a sculptor

Montepulciano b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$457

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$905

Casa il Mandorlo private garden - pool

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$136

Casa Giovanna Ap.1

San Rocco a Pilli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$68

Tuscany Villas La Casetta del Borgo San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect base to see all that Tuscany has to offer” La Casetta del Borgo was the perfect location for my recent trip to Tuscany with my wife. The unit is located in a resort with plenty of amenities including two pools and a very nice tennis court with faux grass that can be used for a small fee. It is a 10 minute drive to Montaione where one can go for dinner or buy groceries to cook in the unit's kitchen. All the necessary utensils are available to do some home cooking and I enjoyed a number of home cooked dinners and a delicious breakfast every morning thanks to my lovely wife. The main resort building has a restaurant that serves breakfast, lunch and dinner, however I didn't try it out so I can't say anything about it. Paolo, the owner, was a pleasure to deal with. I was having trouble finding the location with my GPS so Paolo had me meet him at his home which is just off the highway from Florence and very easy to find. To ensure that I found it with no problem Paolo drove to the resort while I followed . Once at the resort he had the keys, a nice bottle of wine, and plenty of info about the local area ready for me. Since he knew that I had the flu he even had some flu medication for me in case I needed it! The weather was unseasonably cold when we arrived and the bedding wasn't sufficient, but Paolo came to the rescue and drove over in the rain with more blankets for us. You'll be hard pressed to find a better host at this type of vacation rental. The location was perfect for us as it was very quiet, yet was within easy driving distance of many towns and cities in Tuscany. Smaller towns like Montaione and San Gimignon were within a 10-20 minute drive and Florence, Pisa, Lucca and Sienna were all within an hours scenic drive. If driving into Florence remember that free parking can be found at the Piazzale Michelangelo which is located outside of the ZTL and is a short walk to the Ponte Vecchio, Uffizi and other old city sites. The views are also magnificent! I wouldn't hesitate to recommend this property!

Match: Garden

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Price per night from

$86

Podere Osteria

Pienza apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$309

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

Match: Garden

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Price per night from

$798

Casina di Arceno - Refurbished Farmhouse - sleeps 6 + 2 - pool - Chianti

San Gusme house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$364

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: Garden

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Price per night from

$1,234

Match: Garden

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Price per night from

$1,434

DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$281

Casale Montesoli

Buonconvento house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$881

San Gimignano villa rental

San Gimignano house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 40 minutes

Match: Garden

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Price per night from

$802

2 Bedrooms Flat Crete Senesi

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$56

10 bedroom Siena villa rental

Ville di Corsano house

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 20

Responds fast! avg. 3 hours 40 minutes

Match: Garden

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Price per night from

$1,573

Belmonte House

Castellina In Chianti house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$335

Casale Etruria

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$353

Casale il Gualdo

Radda in Chianti house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Garden

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Price per night from

$516

L'ANTICO GRANAIO

Montepulciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$153

montechiaro Shed

Siena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$695

Siena luxury villa rental

Asciano house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 40 minutes

Match: Garden

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Price per night from

$864

Farm in Chianti

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$771

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rentals in Province of Siena

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