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Province of Siena Rentals

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2,850 Houses

VILLINO

Montisi house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$182

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$137

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$171

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.

Price per night from

$160

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.

Price per night from

$262

Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

Price per night from

$1,044

Monteriggioni Suite 4

Monteriggioni house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$133

Morgana

Buonconvento villa

9 bedrooms / 9 bathrooms / sleeps 18

Price per night from

$1,444

Romantic Cottage in Tuscany

Radicofani cottage

3 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 44 minutes

Price per night from

$103

Beautiful cottage 2/9 people with pool, near Siena

Trequanda villa

2 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$119

Cesira Palazzina

Val d'Orcia b&b

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$177

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$232

Cottage in Chianti, with pool, spa, and wonderview

Castellina In Chianti cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$250

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

Nusenna villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$213

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$160

B&B Il Pozzo - Giuggiolo

Sinalunga b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$57

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$568

Rental house in the centre of this Chianti village

Castellina In Chianti apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 33 minutes

Price per night from

$80

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$80

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$308

Lovely apartment in a small winery

Castellina In Chianti barn

2 bedrooms / 1 bathroom / sleeps 4

“The real heart of Tuscany, a dreamholiday” For many years we have spent every summerholiday in Italy. It took only little time trying out various locations before we realized that the Casina at Setriolo was the perfect place and since then we haven't been anywhere else. The place is beautiful, quiet, romantic. The views from the terrace breathtaking. The garden lush and colourful, the swimming pool surrounded by lavender and green hedges. The house itself offers everything you need, it is compact, practical and yet full of character. And situated in the heart of the Chianti region of Tuscany all the main attractions are nearby. And even after having bought our own house in Umbria, we will go on visiting Setriolo for the dear owners and the beautiful memories.

Price per night from

$148

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

Castellina In Chianti cottage

1 bedroom / 1 bathroom / sleeps 2

“Very Romantic and Relaxing” Podere Patrignone, is a very well managed holiday/vacation destination. Simon and Verity (owners), went to great lengths to make sure ours and other guests stays we're relaxing and enjoyable. Always available, but rairly needed, they have created an "old world charm" and very natural feel to their quiet olive orchard. Whether it's a romantic getaway (ours was our 10th wedding anniversary), a quiet place to retreat and relax, or just a quaint Tuscan "centrally" located place to stay, we highly recommend it. Everything on their website was exactly as advertised! What isn't as highly advertised, but left to us to tell about, is the care and passion Simon and Verity have for making this such a special place to stay. And don't miss the weekly group dinner. Verity goes all out for that, and it's a delicious Tuscan style feast with a wonderful group of people! We can't wait to return!

Price per night from

$171

CASA ALADINA: STUDIO RIGHT IN THE CITY S.GIMIGNANO

San Gimignano apartment

/ 1 bathroom / sleeps 3

Price per night from

$80

Private Elegant Zen Cottage in Siena Tuscany

Torri cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$125

Charming Apartment in Historic Center of Montepulciano, Tuscany

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 52 minutes

Price per night from

$80

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

Montalcino house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$111

Villa with Pool and Jacuzzi private Deal 2023

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$110

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

$149

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. 1 hour 35 minutes

Price per night from

$106

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

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

“Wow! A relaxing well appointed holiday home” This is central rural position 6ks from Torrita di Siena makes it easy to enjoy beautiful Tuscany. With easy day trips with a car to Seina, Arezzo, Cortona, Castiglione del Lago or Firenze to name a few.Quiet, comfortable with a very suitable kitchen facilities, all helping to make a very relaxing home base in the middle of the wine area. A good map and GPS navigation system is a must to find your way in this amazing countryside.

Price per night from

$129

Authentic 3 Bedroom Farmhouse

Castellina In Chianti b&b

3 bedrooms / 2 bathrooms / sleeps 8

“Ankommen und sich Wohlfühlen !!” Es ist etwas besonderes auf poderi val verde zu sein.Es beginnt schon mit dem Begr?ssungs Essen an dem abend lernen sich alle G?ste kennen und man bekommt das besondere Toskana Gef?hl.Gutes essen, guter wein, super Wetter einfach la dolce Vita.So beginnt Urlaub. Das gel?nde ist einfach toll.?berall Blumen und Kr?uter und ums Gel?nde herum Natur und Ruhe.Keine Stadtger?usche wie autos usw.So kann man sich wunderbar rund um den Pool auf den Liegen oder sitzm?glichkeiten erholen. Die wohnung die wir hatten war klasse wir haben uns sehr wohl darin gef?hlt.Obwohl wir die meiste Zeit auf unserer Terasse waren.Was auch besser ist wenn man Kontakte zu anderen G?sten sucht. Die einrichtung der Wohnung ist sehr sch?n,hier merkt man den guten Geschmack von Frau Eder.In der Wohnung hat man das Gef?hl hier leben nicht nur Urlauber sonder Bewohner.Das ist besonders bei der K?che,da wir sehr gerne und gut kochen ist es toll so eine gut eingerichtete K?che vorzufinden.Ich konnte von Caprerse ?ber Zucchini-Frittataund Zitronen-Knoblauch-H?hnchen und viele andere Gerichte ohne Probleme zaubern,weil allle K?chenutensilien da waren.Und fehlt wirklich einmal etwas geht man zu Ulricke (Frau Eder) und sie hilft sofort.Sie gibt auch die besten Tips.Wie zum beispiel das einkaufen. Besonders kann ich empfehlen die M?rkte:Dienstag in Poggibonsi,Mittwoch in Siena,Samstag in Casttelina,Sonntag in Panzanno.Toll ist auch der Metzger in Castellina. Was f?r uns als Naturliebhaber klasse an Poderi Val Verde ist, die m?glichkeit direkt von hier supertolle spazierg?nge oder Wanderungen zumachen.Zum Beispiel nach Lilliano durch Wald ?ber H?gel und Weinberge.Oder nach Panzanno ?ber einen H?henkamm mit super aussicht und nat?rlich durch Weinberge. Nat?rlch kommt die Kultur nicht zu kurz Jeder kleine ort hat seine Reize besonders unsere lieblings Stadt Siena. Und abends sitzt man wieder auf seiner Terasse geniesst das Essen dazu einen super tollen Chianti. .

Price per night from

$263

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

Acquaviva di Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$136

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!!

Price per night from

$569

Accommodation near Pienza Tuscany

Pienza apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$205

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.

Price per night from

$171

Tuscan countryhouse apartment in San Gimignano

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 51 minutes

Price per night from

$97

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

7 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 43 minutes

Price per night from

$778

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!

Responds fast! avg. 2 hours 59 minutes

Price per night from

$1,569

Viewing 38 of 2,850
rentals in Province of Siena

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Top Destination reviews

Villa Patrignone 7 bedroom Tuscany villa with pool
La Vista Bella

My family and I stayed in the "villa" at this beautiful Tuscan estate. Gorgeous views and sunsets to die for. Rosemary hedges line the property. Close in proximity to all of the wine towns along the Chiantgiana, as well as Sienna. The accommodation was charming and we loved the feeling of old Tuscany in everything from the furnishings to the beautifully hand stitched sheets on our beds. Simon and Verity were awesome to deal with before our arrival and even better in person. My grandchildren ages 10 and 5 made fast friends with their boys and I am sure will have pen pals forever,or until we return. We were sorry to go onto our next adventure, it was a teary send off for all the children. A Tuscan dream come true. Thank you, Simon, V, Max, Sam and Dawn too! Warm regards, Antoinette, Lee, Billy, Kelly, Vivian and little Billysee more
Romantic farm for 2/4 persons with pool near Siena
Gorgeous authentic italian stone house with a village within walking distance for eating, supermarket, info centre,wifi.

An authentic italian stone home stylishly renovated and appointed yet with old world charm and character. Two stories large bedroom/bathroom downstairs leading out to casual seating and upstairs via spiral staircase to large kitchen/sitting eating area. Very spacious and comfortable for our weeks stay. A lovely option was the clean and fresh swimming pool to relax by. Wonderful location to explore the beauty of Tuscany and Margheritas very useful and correct information on touring sights and eating places a great help. We would recomment this accommodation to any couple for a holiday.see more
CASA DANIELA - ONLY YOU AND YOUR FAMILY -
Best holiday in peacefull location

We spent a very relaxing holiday in Danielas house. The apartment is well equipped and has a great pool and patio to rest in peace.We loved to watch deers who visit us daily on the property. We felt welcome by the owner, Daniela was kind and atentive. The place is close to Casole dElsa, a nice village, 25 minutes to walk, a place to eat and relax . Volterra ( in special ) and Cole val dElsa worth a visit, Florence, Pisa and Siena are easy to reach by car. A car is needed (preferable a small one because of narrow roads) because the location is remote, far from shops, and is better to fill up with food and beverages before arrival. The house itself is a little dark, bathroom needs some renovation, but most annoing was mosqitos. So be prepared and ready with all the weapons against! We recommend this house to whos looking for a peaceful vacation.see more
LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS IDEAL FOR COUPLES
We had a most enjoyable 2 week stay in your apartment!

The location was perfect for visiting the Tuscan Hill towns and local Wineries. The apartment was well equipped to satisfy all your needs. The Terrace was beautiful and we had many nights sitting outside with a glass of wine looking at the scenery. Hopefully we will be able to return in the future!see more
Siena historic centre apartment Mimosa
Beautiful apartment

A friend and I stayed for 5 days, and were delighted with this accommodation. It was bright, very clean and comfortable. Very close to the town centre, Silvia was there to meet us on arrival, went through how everything worked in the apartment, gave us detail on events going on that week in Siena, and highlighted some places of interest in the map. She texted during our stay to ensure everything was fine. She also offered to call a taxi for us on departure. Overall a great experience. Thank you Silvia for the personal touch and effort you put in, it helped make our stay in Siena very memorable!see more
APPARTAMENTO SOLANGE SIENA
Great

It was a wonderful experience to have visited this location, great amenities, great location and historic surroundings. I hope to visit this apartment again sometime in the future. … see more

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