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House vacation rentals in Province of Siena

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Popular amenities for Province of Siena house rentals

House rentals with a pool

Guest favourite
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars6 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Guest favourite
Home in Gavorrano
5 out of 5 average rating, 11 reviews

Pirite Dependance Agriturismo La Miniera (swimming pool)

HélèneRating, 5 stars6 months ago
Nice little house in a very large enclosed yard with a beautiful house in front with several rentals. Functional, enough to cook in terms of utensils. Provide extra bath towels for the pool. Nothing is closed or locked outside between rentals (ideal place to organize a family stay, family reunion or with friends, the setting is so ready) with this beautiful swimming pool (totally fenced for security) plenty of space around, it's not disturbing if there are several people, deckchair, it is cleaned every day. Very green setting with farm animals (ponies, donkeys, pigs, cow and her calf, etc.) nearby and wild boars. Just for info it's nestled, no view but rejuvenating because in nature. We did not meet Giancarlo who is very responsive to messages but we met his son with his small family who are very friendly, give advice and information, they like to exchange. Thank you all
Superhost
Home in Asciano
4.83 out of 5 average rating, 12 reviews

house with pool between Siena and Valdorcia

MatthewRating, 5 stars1 week ago
Had a wonderful 4 nights in this very peaceful villa in Tuscany. Check in with Ricardo was easy, very friendly. We had no problems in our stay so didn’t need to bother him, so while he lives on site it felt like our own villa for the whole time. The pool was very kindly opened early in the season for our kids to use. Wonderful views from the pool terrace. Only suggestion is for simple things like salt, pepper, balsamic etc to be left so to avoid every guest having to buy new. . But overall this was a 5 star stay and we would highly recommend, thank you!
Superhost
Home in Ville
4.79 out of 5 average rating, 29 reviews

Independent Tuscan Villa Siena with Pool (7+1)

RonRating, 5 stars7 months ago
We stayed for a week and had a wonderful time. The house is well maintained and exactly as per the description provided. Giovanna and her family are highly responsive and responded instantly to any queries we had. We would highly recommend anyone wanting to go to the Toscana to stay at this wonderful house.
Top guest favourite
Home in Serre di Rapolano
4.97 out of 5 average rating, 74 reviews

L'Olivo - detached villa with swimming pool

MartaRating, 5 stars7 months ago
Amazing place in a quiet area with a beautiful view of the countryside. Climate cottage equipped with everything you need. Together with our dogs we felt like at home. Bruna is an incredibly warm and helpful person. Thank you for a wonderful time.
Guest favourite
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars6 months ago
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!
Top guest favourite
Home in Arezzo
5 out of 5 average rating, 30 reviews

Beautiful barn among the olive trees

AnitaRating, 5 stars1 week ago
We are delighted with our stay, the house was what we were looking for, authentic exotic, crazy charm
Top guest favourite
Home in San Giovanni D'Asso -Montalcino
5 out of 5 average rating, 22 reviews

Pasqui Villas :Historic mansion La Consuma

MariaRating, 5 stars6 months ago
Our stay at Historic Villa La Consuma was unforgettable! The villa combines historic charm with modern comfort, set against stunning Tuscan landscapes. Spacious rooms, elegant decor, and lush gardens make it the perfect escape. Federica, our host, was exceptional—welcoming, attentive, and knowledgeable, adding personal touches that made our stay special. Thanks to her recommendations, we easily explored nearby gems like Montalcino and Montepulciano. For anyone seeking an authentic and luxurious Tuscan experience, Villa La Consuma is a dream come true.

Weekly house rentals

Superhost
Home in Contignano
4.77 out of 5 average rating, 31 reviews

Noi 2 Vacanze - Dario's House

LaurenceRating, 5 stars7 months ago
The views are beautiful. Peaceful neighborhood. However, the kitchen is missing several items for cooking.
Superhost
Home in Castellina in Chianti
4.75 out of 5 average rating, 60 reviews

Casa Belvedere with Pool

GeoffreyRating, 5 stars7 months ago
The photos do not capture beauty and character of this place. Very comfortable and high spec renovation of the historic farmhouse ... spacious, relaxing, huge pool, bedrooms stayed cool even as temperature reached 30+ degrees. Great restaurant just round the corner, and top wineries nearby. Fantastic weekend was had, thank you Maurizio!
Superhost
Home in Montefollonico
4.89 out of 5 average rating, 18 reviews

[15 min da Montepulciano] Villa Chiara

JoeRating, 5 stars7 months ago
Great location and the 2 full size bathrooms were nice!
Guest favourite
Home in Montebenichi
4.88 out of 5 average rating, 16 reviews

The Montebenichi Dovecote

RoisinRating, 5 stars3 weeks ago
All I can say is wow. This house was amazing it had everything that you needed. It was spotless and had extra blankets and towels. It had loads of household supplies and I really felt like it was a home away from home. The views are spectacular….. like something out of a movie, they really take your breath away. Sharyn was so helpful and gave me great instructions on how to get there and the amenities around the area. Cristina and her son were there to welcome us and were amazing. I can’t thank you enough. We are already planning our next stay for longer.
Guest favourite
Home in Arezzo
4.91 out of 5 average rating, 85 reviews

Daniele&Patrizia-Family's House, relax and view

LisaRating, 5 stars6 months ago
The views from this guest suite will be some of my favorite memories of Tuscany. I highly recommend going outside 30 minutes before sunrise to watch the sky change colors against the mountains while you take a deep calming breath looking across the valley below. The guest house is compact, modern, and clean. And Patrizia and her family are just next door, available and friendly if you need anything.
Superhost
Home in San Gimignano
4.84 out of 5 average rating, 44 reviews

Uliveta, cosy villa in country of San Gimignano

NaiyaRating, 5 stars6 months ago
What an absolute gem of a place. Lovely three bed property, that was spacious and clean. The gardens and view were breath taking. Many vineyards which are at a walkable distances. The town was around a 40min walk but we didn't mind this as it was so peaceful. Concetta was such a welcoming host, and the best part was the lovely meal she prepared for on my birthday. It was well worth the extra money. Wish we could have stayed longer to explore more. Thank you concetta!
Superhost
Home in Rietine
4.85 out of 5 average rating, 206 reviews

Gaiole in Chianti Poggio Casabianca

MonicaRating, 5 stars5 months ago
What a great getaway!! We hope to make it back soon!
Top guest favourite
Home in Montepulciano
4.97 out of 5 average rating, 35 reviews

A moment of relaxation

FrancescaRating, 5 stars5 days ago
I recommend this apartment to visit the Val d 'Orcia , the apartment is large and clean, nearby there are several shops, and the host Francesca is very helpful

Private house rentals

Guest favourite
Home in Radda in Chianti
4.85 out of 5 average rating, 177 reviews

Tuscany House "La Querce Sola"

EricRating, 5 stars1 week ago
Rosanna and her country house are as great as all the reviews say. The house is spacious, comfortable, clean, quiet, charming with beautiful views of the surrounding hills. Great place to relax with family. If you intend to use the oven ask for instructions, it works fine but the operation wasn’t intuitive for us. Also bring plenty of bottled water, the house supply is fine for washing but not for drinking/cooking. Rosanna gave us great recommendations for dining and sightseeing in the Radda/ Castellina area, great place at a reasonable rate!
Guest favourite
Home in Civitella Paganico (GR)
4.94 out of 5 average rating, 18 reviews

Podere Vignali by Interhome

SimoneRating, 5 stars7 months ago
Really beautiful place and beautiful surroundings. All communication went smoothly. Very clear instructions and descriptions sf amenities. The host will be in touch with you a few dsge before arrival and check in was super easy.
Home in San Gimignano
4.75 out of 5 average rating, 4 reviews

Villa Alba by Interhome

BernieRating, 5 stars31 months ago
Casa Alba was fantastic. We had a wonderful stay. We renewed our vows, at Casa Alba, to celebrate our 10 year wedding anniversary & it was a dream day 🤗 Luigi & his wife were there to welcome us & couldn't have been friendlier. My sister, brother in law & their toddler stayed the week with us & I can definitely say we loved it & would absolutely return 🙌 its very close to San Gimignano for everything you could need.
Top guest favourite
Home in San Gimignano
4.97 out of 5 average rating, 38 reviews

House with private pool, 2 independent apartments

KellyRating, 5 stars3 months ago
Beautiful, comfortable and cozy house. We had amazing days with friends and the kids loved the place. The owners are always available and super attentive. I highly recommend it!!
Home in Radda in Chianti
5 out of 5 average rating, 9 reviews

Le Bonatte by Interhome

CarlRating, 5 stars6 months ago
Joy (the owner) is a joy! She is one of the best hosts we’ve had on this platform. Flexible checking, due to delayed flight. Rooms were bigger than anticipated and beautiful. Lovely rustic Tuscan charm of a property. Plenary of recommendations at the property for local restaurants and activities. Can’t recommend this property enough!
Home in Castellina Chianti SI
5 out of 5 average rating, 4 reviews

Capanna di Sotto by Interhome.

AntjeRating, 5 stars8 months ago
we immediately felt comfortable 7 d enjoyed the stay very much. A ideal starting point for excursions.
Home in Cortona
4.87 out of 5 average rating, 15 reviews

Lucia by Interhome

ChristophRating, 5 stars6 months ago
The terrace was great, and the entire place had a quiet and peaceful feeling.
Top guest favourite
Home in Castiglion Fiorentino
5 out of 5 average rating, 17 reviews

Volpe by Interhome

MartinRating, 5 stars5 months ago
It was an absolute delight to stay at this gem of a property. We booked for 10 days and had a chance to enjoy and explore the surrounding areas. The house is spotless, comfortable, spacious, and fully equipped with modern appliances. So it has exceeded our expectations and would love to book it again in the future. Our host Alberto, is welcoming and very friendly, making the process of checking in and out quite seamless. My overall impression is 10/10.

Destinations to explore

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