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Castle vacation 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 rentals

Top guest favorite
A sunlit view of a tranquil outdoor area features a swimming pool surrounded by stone pathways and manicured greenery. The landscape includes historic buildings and a tall clock tower, set against a backdrop of rolling hills and open sky.
Private room in Serre di Rapolano
5 out of 5 average rating, 63 reviews

Castello delle Serre B&B: Pool Cottage/Standard

JasmineRating, 5 stars1 week 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!
The dining area features a red tablecloth draped over a large dining table, accompanied by a dark wooden chair. The walls are adorned with rich burgundy paint and historical artwork, while natural light filters through large windows framed by heavy red curtains. A rustic chandelier hangs above.
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 stars9 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 stars10 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.
A well-maintained garden features neatly trimmed hedges and decorative planters. The landscape is dotted with cypress trees, complementing the open Tuscan countryside in the background. A charming stone building is seen in the distance, surrounded by lush greenery under a cloudy sky.
Farm stay in San Rocco a Pilli
4.2 out of 5 average rating, 5 reviews

Prestigious apt typical farm breath-taking views

GregRating, 5 stars70 months ago
Great space, such character and a good place to relax away from the city life
Guest favorite
A cozy bedroom features a spacious bed dressed in soft linens, complemented by an elegant armchair. Natural light enters through a window adorned with a flowing curtain, highlighting the simplicity and charm of the space.
Private room in Monteroni d'Arbia
4.92 out of 5 average rating, 36 reviews

B&B - Suite in Castle near Siena

LucasRating, 5 stars8 months ago
We had such a lovely time staying at Giovanni's villa. He was super attentive to everything and gave us daily recommendations for restaurants, points of interest, and where to really feel like a local. The villa is beautiful -- If you are looking for a Tuscan countryside escape this is the place to be. The rooms are tastefully decorated and transport you back in time. The daily breakfast is divine and one can really feel the love the family puts into maintaining this place. Would love to return -- Having a car is essential
The rustic exterior of the stone house is highlighted by its weathered façade and central gabled roof. Surrounding greenery and a pathway lead towards the entrance, while a decorative flower arrangement adds a touch of color to the peaceful countryside backdrop.
Farm stay in Chiusdino
4.38 out of 5 average rating, 8 reviews

Palazze Torre -

DominikRating, 5 stars43 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.
An expansive courtyard is illuminated by warm lights, showcasing the historic architecture of the building. Towering trees frame the scene, while decorative potted plants line the pathway, enhancing the serene ambiance of the estate during dusk.
Private room in Trequanda
4.81 out of 5 average rating, 37 reviews

Superior Room in Abbadia Sicille Relais

Hans-JürgenRating, 5 stars2 weeks ago
Abbadia Sicille is an accommodation you don't find every day: a successful mix of old and modernization. The ristorante is excellent, of course, all this comes at a price.
Villa in Castiglione del Lago
4.56 out of 5 average rating, 36 reviews

Magic Umbrian Villa, Private Garden Stunning Views

HelenRating, 5 stars10 months ago
Beautiful home with such a beautiful garden! A communicative and a considerate host. Highly recommend!

Destinations to explore

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