Province of Siena Rentals

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2,072 Houses

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$162

Beautiful Independent Tuscan Cottage For 2 With Spectacular Views

San Casciano dei Bagni cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Postcard perfect setting and views!” My husband and I rented La Ginestra for one week in October. It was a perfect choice for us--size of the house, its location, amenities, and the incredible vistas from every window and door. We felt that in choosing La Ginestra we had a real Tuscan experience, as the town is very "untouristy" and genuine. We loved shopping in the local stores, sipping coffees and wine at the local bar/terrace, and feeling like locals for one week. Richard has done an outstanding job of furnishing the lovely house, providing lots of local information, and responding to us in a timely manner. Maruizio, the caretaker, was a joy to meet and a wonderful source of more information. We highly recommend La Ginestra!

Price per night from

$218

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$232

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 4 minutes

Price per night from

$113

Cesira Palazzina

Val d'Orcia b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$194

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

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$299

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$175

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.

Price per night from

$187

CASA ALADINA: STUDIO RIGHT IN THE CITY S.GIMIGNANO

San Gimignano apartment

  • 1 bathroom
  • sleeps 3

Price per night from

$88

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.

Price per night from

$234

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

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$191

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

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$211

Accommodation near Pienza Tuscany

Pienza apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$225

Piettorri Rosemary

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Price per night from

$155

Guidi

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$119

CASTELLO DI MONTALTO - 2 bedroom Villa in Chianti

Castelnuovo Berardenga house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$288

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

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$174

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.

Price per night from

$234

Casa Borgianni. Villa Caprera, Siena Farmhouse.

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$299

Ciliegio house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$100

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

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$914

Casa Giovanna Ap.1

San Rocco a Pilli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$69

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$413

Podere Osteria

Pienza apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$390

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

Price per night from

$807

Tuscan Tower - A unique castle apartment

Montefollonico apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

“Such a gem in a magical place!” Our weeklong stay at the beginning of October was nothing short of magical. Such an incredibly serene and peaceful setting with far reaching views of the area from the Tower. Located in an intimate Tuscan village filled with history, beautiful medieval architecture and the loveliest people who went out of their way to help you. Wendy and John went above and beyond to ensure our stay was comfortable and to steer us to the must see sites, restaurants and wine tastings. The apartment was clean with all the necessary kitchen and laundry amenities, and the space was generous with two bedrooms and two bathrooms, making the layout ideal for two couples. The village had some outstanding restaurants and a well stocked grocery store. Superb location for visiting many of the top tier wine producers of Montepulciano and Montalcino. Would love to return someday.

Price per night from

$228

Price per night from

$1,432

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.

Price per night from

$299

Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Return visit” One again we enjoyed our visit to this well run set of apartments. They are ready on time, cleean and well equiped. A caretaker lives on site to provide backiup if needed. The gardena and pool are tell tended and maintained. Montipulciano is 10 mins away by car. Be aware that it is in the middle of the countryside with no shops or restaurants nearby.

Price per night from

$213

Country House at Antico Podere in Montepulciano, Tuscany

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$150

Hermitage Cloister

Gaiole in Chianti apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$392

Noci bedsit house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$63

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

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$312

Casale Stine

Monteroni d'Arbia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$149

House Giobatta A

Lucignano d'Arbia house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 35 minutes

Price per night from

$250

Casale Montesoli

Buonconvento house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$890

Quercia house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$125

Suite Le Camelie

Caprera apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$150

Viewing 38 of 2,072
rentals in Province of Siena

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Top Destination reviews

Exclusive Tuscan Villa with pool,hot tub,A/C,7 bd, free wi-fi,15 km from Siena
Perfect in every way!!!

What can I say….???We have already decided to book this Villa for next year…..one week is not enough, we will be back Villa "Le Caggia" was the setting for a fabulous vacation with our family. The location was perfect as we could take a number of day trips to explore Tuscany, from Florence(one hour driving) to Siena(20 minutes) and many other lovely towns in the Chianti or in the Orcia valley Waking up in the morning to see the fields spread below us was absolutely incredible, the Villa is spacious, very clean and decorated with care in every detail. A huge garden with a beautiful swimmingpool where you can relax while sipping a good Chianti wine, always cherished by the magical breeze(it is a Le Caggia trademark that you can only find here) ever-present and pleasant. Last but not least, Fabio e Jacopo were terrific hosts, always helping us, have made our stay more enjoyable and memorable…. Absolutely do not miss their welcome dinner and their cooking class….I already used their recipes to prepare a dinner and I have delighted all my friends, friends that will be with us for the second time at Le Caggia Absolutely the perfect place for those who want to enjoy Tuscany.see more
Villa Le Bolli: a vacation like at your home!
A true dreamspot in the heart of Tuscany

Our trip to Le Bolli turned out to be one of our best holidays ever. A long-time friend of ours had booked the house to round up old buddies for a get-together on the occasion of his upcoming birthday. And there it was, the wonderful house with the lovely garden, the huge kitchen and the cosy living-room with the fire-place. We liked the place from the first moment on, our two kids were perfectly happy with the other 4 kids, the pool and Luigi, the cat. We had a great time with our grown-up friends and enjoyed long hours of talk, laughter and red wine. Pierangelo is a great host and a formidable cook. He showed up with a few local helpers and prepared a great farewell dinner for all of us (15 persons). It was a shame we could not stay another week on top. Le Bolli is a true dreamspot in the heart of Tuscany. Go there and you will find out for yourself.see more
Il Granaio 1 Bedroom Tuscan Farmhouse
Tuscany at its best!

We stayed at the property Il Granaio for 1 week and added two days because we fell in love with it the moment we saw it. First of all, the booking was done very professionally right up to the point when we phoned from San Gimignano for directions and were guided right to the gate. The owners of the property Guiseppe and Rosina welcomed us warmly and showed us the cottage we had booked. We loved it the minute we set foot into it. The view over vineyards and olive groves to the towers of San Gimignano on the hill was breathtaking. The cottage itself was well appointed, clean and comfortable. The living room-kitchen was well appointed and had everything one would need. The bedroom was spacious and the bed very comfortable. The cottage was advertised for 2 to 4 people. I would say that it is perfect for a couple and maybe a couple with 1 child. I would find it to be too small for 4. The grounds were immaculately kept, the pool sparkled and the relaxed atmosphere made for a perfect Tuscan experience, especially because the towers of San Gimignano were always visible. The property is only minutes from the town of San Gimignano and a super market for grocery shopping. It is close enough to visit such Tuscan treasures like Siena, Pisa, Voltera, Greve di Chianti and more. I am mobility challenged so what made it even more special for me was the help of Guiseppe. Tthere were three steps to get into the cottage. Guiseppe, without having to ask, immediately brought boards and built a ramp which made it possible for me to enter the cottage with my scooter. This was far beyond the call of duty and very much appreciated. Rosina had offered a unit that had no steps but once I had seen the cottage I didn't want to give it up, so Guiseppe's ramp was a real gift. Because we loved our stay so much, we added 2 more days. While we had to vacate the cottage for the next guests, Rosina offered us the accessible unit, which we were able to enjoy for these last two days. It was a dream vacation and I can only recommend this lovely property to anybody who likes a peaceful, relaxed vacation near beautiful San Gimignano.see more
Tuscan Tower - A unique castle apartment
Outstanding

Cannot wait to get back! Amazing apartment in one of my new favorite areas of the world. Next time, we'll just make sure to stay longer...4 nights wasn't nearly enough. … see more
Casa Borgianni. Villa Caprera, Siena Farmhouse.
A perfect Tuscan retreat

We have just returned from Italy, the first week of which was spent at Villa Caprera. We already loved Tuscany, as we have been twice before. However, nothing prepared us for the wonderful find of Villa Caprera, and we didn't want to leave. The location is perfect for our beloved Siena, and is in the heart of rural tuscany. The booking was efficient, and queries dealt with quickly and in a friendly, helpful manner by Simona. We arrived to the warmest of welcomes from Daniella, with lots of homely touches like homemade cake, wine, milk, olive oil and balsamic. The villa itself is beautiful: clean, tasteful, comfortable and full of love. Everything we required was provided, and more. Fresh vegetables and fruit were brought to us by lovely Daniella, and we couldn't have asked for more. It is even more beautiful than the photographs suggest. We will definately be returning to Villa Caprera. Thank you so much Daniella and Simona for everything.see more
Beautiful Independent Tuscan Cottage For 2 With Spectacular Views
Wonderfully comfortable Tuscan cottage with spectacular views

We've just returned from a week at La Ginestra and can't possibly say enough nice things about it. The house is well situated, around halfway between Rome and Florence, and just a short drive from the train station at Chuisi. Nearest towns are Celle Sul Rigo and San Casciano dai Bagni, both wonderful small towns with local restaurants, butchers, etc - those looking for an authentic Italian experience don't need to look any further than this! The house itself is set just outside the town of Celle Sul Rigo, so walking distance from restaurants and shops. It is very well situated, on a plot filled with olive trees and overlooking a valley with views we admired for hours (and days) on end. To be able to sit outside at sunset, as the valley gradually turns purple and blue in the fading light, with a glass of wine in hand is an experience we won't soon forget. The house itself is very well equipped and perfect for two. You can tell it has been set up as a home rather than as a holiday rental. It had everything we needed, from proper wine glasses, a range of pots and pans, to a fan for the summer heat. The bathroom was also well equipped, with good water pressure and plenty of hot water in the shower. There was even a washer and separate dryer, perfect for a week long stay. The fireplace was lovely at night, making it a treat to come inside at dark and sit beside the fire. From La Ginestra, day trips to Montepulciano and the Val d'Orcia were only a short drive, and very achievable. We would not hesitate to recommend La Ginestra to anyone, and hope to return ourselves very soon.see more

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