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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 stars7 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 San Giovanni d'Asso
4.77 out of 5 average rating, 52 reviews

Tuscan Villa Poggetto Montalcino

SamRating, 5 stars7 months ago
Villa poggetto was a beautiful and quiet retreat. Our family used it as a base for seeing other parts of Tuscany and hired a car so it was perfect. It has basic amenities and the pool is in great condition. Only critique is the doors don’t lock well (not really a concern as the area is quiet) and as it is rural there are animals around such as mice and cute local cats. Gastone was a great host who allowed us to check in at 11pm when we were running late. He is very responsive and kind.
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.
Superhost
Home in Cortona
5 out of 5 average rating, 3 reviews

Private villa with pool & AC, few km from Cortona!

MartinaRating, 5 stars1 week ago
The place is as pictured, in the Tuscan countryside. A slice of paradise where you can only hear the sounds of nature. The host and his son were super friendly and helpful in accommodating our requests. We had the opportunity to check in early and late check-out. The house is spacious and equipped with everything you need. The pool is great for relaxing and the outdoor table great for outdoor dining and grilling. We'll definitely be back
Top guest favourite
Home in Arezzo
5 out of 5 average rating, 34 reviews

Beautiful barn among the olive trees

LizRating, 5 starstoday
Barbara has a beautiful home in Tuscany. We stayed for an equestrian event and it was literally five minutes from the equestrian center, they were helpful with all information, they loved our dog, were very dog friendly and we will definitely look forward to staying with them again next year. Amazing hosts, Barbara and her husband.
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 stars7 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 stars8 months ago
The views are beautiful. Peaceful neighborhood. However, the kitchen is missing several items for cooking.
Superhost
Home in Lucignano
4.78 out of 5 average rating, 9 reviews

Beautiful property between Siena and Arezzo

TimRating, 5 stars21 months ago
we had a very nice stay. The whole place was very clean. Highly recommend taking something against the mosquitoes. the only criticism was the chairs on the terrace, as 2 have shackled heavily, there should be a replacement here.
Superhost
Home in Castellina in Chianti
4.75 out of 5 average rating, 60 reviews

Casa Belvedere with Pool

GeoffreyRating, 5 stars8 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
4.89 out of 5 average rating, 18 reviews

The Montebenichi Dovecote

StephenRating, 5 stars2 weeks ago
We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again
Guest favourite
Home in Arezzo
4.91 out of 5 average rating, 86 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 stars7 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, 207 reviews

Gaiole in Chianti Poggio Casabianca

MonicaRating, 5 stars6 months ago
What a great getaway!! We hope to make it back soon!

Private house rentals

Guest favourite
Home in Radda in Chianti
4.85 out of 5 average rating, 178 reviews

Tuscany House "La Querce Sola"

Klery CastilloRating, 5 stars2 weeks ago
I already loved the house from the photos and I have to say that these do not do justice to Rosanna's wonderful and welcoming house. It is a lived-in home, with books to read for all ages and minds, firewood, kitchen stocked as at home. Nothing is missing. It is the ideal place to unplug and enjoy the here and now, to find yourself in balance with nature. I was in the family with small children and dogs. Everything is perfect, we will definitely be back.
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.
Home in Radda in Chianti
5 out of 5 average rating, 10 reviews

Le Bonatte by Interhome

CarlRating, 5 stars7 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 Roccastrada
4.67 out of 5 average rating, 6 reviews

Poggiolo by Interhome

ElizaRating, 5 stars20 months ago
Very beautiful place, it was so quiet and relaxing. The host was also very relaxed and such a sweet man. You really can feel the Tuscany vibes! Would definitely recommend this place if you want to chill and want to stay in a quiet and peaceful place!
Home in Cortona
4.87 out of 5 average rating, 15 reviews

Lucia by Interhome

ChristophRating, 5 stars7 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 stars6 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.
Home in Roccastrada
4.93 out of 5 average rating, 14 reviews

Casa la Selvolina, by Interhome

JonasRating, 5 stars2 weeks ago
Very Kind and lovely guys, quiet and relaxing area. I loved it

Destinations to explore

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  3. Tuscany
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