Province of Siena Rentals

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2,092 Houses

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$160

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$185

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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$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.

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$332

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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$1,033

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$229

Morgana

Buonconvento villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

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$1,709

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 11 minutes

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$111

Cesira Palazzina

Val d'Orcia b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$191

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

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$230

Cottage in Chianti, with pool, spa, and wonderview

Castellina In Chianti cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$292

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

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$295

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$173

B&B Il Pozzo - Giuggiolo

Sinalunga b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$62

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$615

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$372

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.

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$185

Private Elegant Zen Cottage in Siena Tuscany

Torri cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$136

Charming Apartment in Historic Center of Montepulciano, Tuscany

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$86

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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$173

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool!

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

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$194

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

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$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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$151

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$208

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!!

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$738

Accommodation near Pienza Tuscany

Pienza apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$222

Casa Bartoli at Borgo Mummialla-your Tuscan home !

San Gimignano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“A jewel in the heart of Tuscany.” Booking very easy helped by the owner. Apartment exceptionally comfortable with all the facilities we required. There was no problem moving in thanks to being met by Fabio when we arrived. A beautiful location with amazing views of Tuscany. An ideal spot for touring and visiting the many medieval towns in this area.

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$185

Tuscan countryhouse apartment in San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$105

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

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$770

Cozy Collection of Villas in Tuscany

Montalcino villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 26

“Great stay- we hope to return!” We truly enjoyed our stay here. Matteo was a wonderful host and even met us outside of town to make sure that we did not get lost on the way to the agriturismo. The room was clean and very comfortable, especially important since we brought our 3 month old baby. The kitchenette was very useful and had everything we needed. This was a perfect place to stay while in town for Benvenuto Brunello because it allowed us a gorgeous drive and was away from crowds. We even enjoyed Quercecchio's wine, both Brunello and Rosso. Next time, we hope to visit around harvest time!

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$1,697

Piettorri Rosemary

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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$132

Guidi

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$117

CASTELLO DI MONTALTO - 2 bedroom Villa in Chianti

Castelnuovo Berardenga house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$284

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$171

Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful place with beautiful vistas of the hills and valley fr” We were able to stay 5 days and 4 nights in this lovely place. The property was as or better than described. Very comfortable and clean. Everything we needed for the time we stayed there. It was a very nice location to be able to take day trips to Siena, Pienza, Montepulciano, Montalcino and Orvieto on the way back to Rome. Such great views from apt #2. We even saw deer in the evening and morning running through the fields below. Montepulciano is very close and you can be there in a matter of a few minutes to shop at the Conard or enjoy shopping and meals. There are a lot of rules on lists provided to follow regarding trash, cleaning, linens, etc. We didn't see much of the caretakers as they had other jobs/work, a new baby, etc. But they were very pleasant and helpful if we needed anything. This is definitely a place we would go back to again.Once we found it. I am glad we got to the location during the day and not at night. You just really have to believe the directions and keep going. The signs are a bit small and I am glad everyone was looking for them. Please go eat at the 13 Gobbi in Montefollonico about 5-6 miles away on a hill top to the north. You will love it. And have their house wine, great. By the way, a bottle of wine and olive oil was provided upon our stay. Both were very good. Wish I could have bought more of it.

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$194

Casa Borgianni. Villa Caprera, Siena Farmhouse.

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“heavenly” A beautifully appointed home, with mercifully two batherooms, tastefully decorated with all that you need. The kitchen is a dream - everything you need. Lovely crockery, not bottom-of-the-range, and the bed linen also of excellent quality. Easy access to Siena, on the bus-route - useful to go into Siena by bus, because parking can be a nightmare in Siena itself. Lovely view of Siena, from the top floor. So all in all, this is a hard place to beat, if you want a few days, or longer, just to chill-out and relax and you would be forgiven for thinking Maggie Smith is going to come walking up the drive-way...

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$296

4 bedrooms in a tower, home of a sculptor

Montepulciano b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$455

Ciliegio house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$99

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