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Castle holiday rentals in Province of Siena

Find and book unique castle rentals on Airbnb

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Popular amenities for Province of Siena castle rentals

Family-Friendly Castle Accommodation

Farm stay in Castiglione della Pescaia
4.91 out of 5 average rating, 22 reviews

Castiglione della Pescaia-in MEDIEVAL FARM

ElisaRating, 5 stars9 months ago
A little paradise in the Tuscan view. Immediately upon arrival you feel like you're entering a great atmosphere. The castle welcomes you without being imposing because the context is harmonious with the manicured garden full of succulents. Each decor is designed and essential with a vintage style that makes you feel at home. The welcome is perfect every apartment has its own small intimacy space in the common garden. Friendly sociable and passionate, the owners will make you feel at home and recommend activities and treats to eat nearby. My dog (Maremma shepherd) and I were greeted with love and respect despite the large size of the dog. You will not miss the company because many fantastic cats await you for cuddling making the environment cheerful and vital, but without being invasive and annoying. It's the perfect setting in the Tuscan countryside.
Private room in Sarteano
4.57 out of 5 average rating, 7 reviews

Charming studio in a Castle & Farm w shared pool

GregorioRating, 5 stars23 months ago
Beautiful property immersed in the Tuscan countryside. We were extremely satisfied and highly recommend it. Great value
Top Guest favourite
Private room in Serre di Rapolano
5 out of 5 average rating, 64 reviews

Castello delle Serre B&B: Pool Cottage/Standard

JasmineRating, 5 stars2 months ago
Beautiful property in an amazing part of Tuscany. Incredible and friendly hosts who were always so happy to help us, all details had been thought of at the property. The most comfortable bed I’ve ever slept on too!
Private room in San Giovanni d'Asso
4.81 out of 5 average rating, 43 reviews

Montelifrè's castle. Grand Duke's suite

RebeccaRating, 5 stars11 months ago
Not only the place was extremely pretty, Niccolo was one of the sweetest person we have ever met and it is truly a great honor to get to know him and have dinner with him. He would let us borrow his kitchen to cook and invited us to have dinner together. It was such a memorable experience.
Apartment in Sovicille, Siena
4.71 out of 5 average rating, 34 reviews

Agriturismo at Poggiarello (II)

RachelRating, 5 stars11 months ago
We truly cannot rave enough about this place. We had an absolutely perfect week at this property. Elena, Sveva, and Marco were the perfect hosts and every single thing we could ever wish for was at our fingertips. I almost don’t want to tell the world how amazing this Airbnb is, because we want to keep it to ourselves. Truly one of the most spectacular stays we’ve ever had and a perfect way to experience Tuscany.
Guest favourite
Private room in Monteroni d'Arbia
4.92 out of 5 average rating, 38 reviews

B&B - Suite in Castle near Siena

AvianaRating, 5 stars3 weeks ago
Giovanni and Benedetto were wonderful hosts. Could not ask for more. We had the most magical time in this gorgeous castle with a clean and spacious pool, stunning grounds, and a delicious and beautifully displayed breakfast every morning. The family feel of the castle is just wonderful as well--we loved mama! Finally, we had one member of our group organize a surprise dinner for the rest of us to ask us to be her bridesmaids. Giovanni and Benedetto executed it perfectly and even brought us tissues when we all started crying lol. Truly an unforgettable experience. Cannot wait to go back!
Farm stay in Chiusdino
4.38 out of 5 average rating, 8 reviews

Palazze Torre -

DominikRating, 5 stars45 months ago
It's been an amazing time on the wineyard of Spannocchia. The house is beautifully rustical and located in between the hills of wine. Definitely a place worth staying to relax and enjoy.
Apartment in San Donato in Poggio

Apartment in Chianti – B&B

MartinRating, 5 stars109 months ago
Staying with Beatrice and her family was one of the highlights of our trip to the Chianti region. The home was absolutely perfect, from the beautifully decorated living space and bedrooms, to the manicured gardens, and even a wine cellar with local vintages to taste. The location was ideal for visiting Tuscany and easily accessible from the autostrata. Enjoying breakfast in the garden overlooking the Tuscan hills felt like a guilty pleasure. We will certainly be back and we would highly recommend it to anyone.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Castle rentals