Province of Siena Rentals

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1,325 Houses

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$160

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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$1,699

Cottage in Chianti, with pool, spa, and wonderview

Castellina In Chianti cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$291

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

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$295

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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$614

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$111

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$371

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

CASA ALADINA: STUDIO RIGHT IN THE CITY S.GIMIGNANO

San Gimignano apartment

  • 1 bathroom
  • sleeps 3

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$86

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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$123

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

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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$737

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

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

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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$295

Ciliegio house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$99

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

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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$900

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$407

Podere Osteria

Pienza apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$307

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

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$795

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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$668

Tuscan Tower - A unique castle apartment

Montefollonico apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

“Heaven on earth!” This castle apartment, this town and this region of Tuscany were absolutely beautiful, exceeding our expectations! We were 2 couples celebrating our 25th anniversary,and stayed here following our 12 day Mediterranean cruise last October (2012). We had seen amazing countries and places on our cruise, however when we arrived here and climbed the stairs to the tower in the apartment, the view took our "breath away"! This was the highlight of our entire trip! This was the first time we had rented an apartment, and of course a little nervous about the process. Without meeting John and Wendy, they made us feel so comfortable and welcome. The "Welcome Package" that they provide gives you all the information that you need for your stay and any question you may have, you are sure to find the answer in their guide. Located in this amazing medieval town of Montefollonico, you are in the heart of the most beautiful area of Tuscany. John and Wendy include the sights to see and places to visit in their guide, which we followed and were so glad we did! The town provides everything you need, all within a short walking distance - groceries (including wine, spirits and beer) and local restaurants which were all very good. The apartment was perfect for 2 couples,we each had our own bedroom and own bathroom. The beds were very comfortable and all the linens and towels provided were of the highest standard. Just remember no elevators here, so when you first arrive, you must carry your bags up the stairs. John and Wendy let us know that the internet was a little unstable, which it was, but that was okay too. Every daylight moment we spent at the apartment were spent in the tower, enjoying our Tuscany wines, along with our sheep cheese( so good Wendy!) and never getting enough of the beautiful views, the peace all around us, and the sounds of the birds singing. Truly heaven on earth! Thank you John and Wendy for sharing your world with us!

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$227

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

San Gusme house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$363

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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$1,228

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$1,426

La Canonica

Colle di Val d'Elsa apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

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$350

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

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$295

Casa Baiocco // Private Tuscan Villa With Swimming Pool

Chiusi villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

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$140

Noci bedsit house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$62

DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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$280

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$702

"Policiano Suite" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$307

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