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Holiday home rentals in Siena

Find and book unique holiday home rentals on Airbnb

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Popular amenities for holiday home rentals in Siena

Family-friendly holiday home rentals

Guest favourite
Holiday home in Passignano sul Trasimeno
5 out of 5 average rating, 24 reviews

Antico Casale Tiravento - App. con balcone

Marcel SarahRating, 5 stars1 week ago
Antonella, Andreas und nicht zu vergessen Lullu sind perfekte und so entspannte Gastgeber. Sie haben uns jeden Morgen den Start in den Tag mit frischem Brot, Croissants & Kaffee versüßt. Die Wohnung ist bestens und hochwertig ausgestattet. Wir haben uns sofort sehr wohl gefühlt. Der Garten lädt zum Verweilen ein und wird besonders gepflegt. Vielen Dank für diesen besonderen Aufenthalt!
Guest favourite
Holiday home in Matraia
4.91 out of 5 average rating, 106 reviews

"IL FIENILE" rustic stone house

MartinaRating, 5 stars4 days ago
Wir haben den Urlaub mit unseren drei Töchtern (13, 13, 16) sehr genossen. Besonders der Ausblick und der Pool waren fantastisch. Das Haus und die Terrasse sind sehr schön und laden zum Entspannen ein. Toll war es auch, dass wir fußläufig 2 ausgezeichnete Trattorien erreichen konnten, natürlich auf Empfehlung von Marina. Die Straße von Lucca aus ist schmal und kurvig, teilweise etwas aufregend... Wir waren mit einem großen Ford Transit unterwegs.... alles machbar. Man wird oben von der unglaublichen Aussicht belohnt, besonders nachts mit den Lichtern von Lucca, den Sternen und den Glühwürmchen. Ein schöner Ort mit hilfsbereiten Gastgebern.
Guest favourite
Holiday home in Cortona
4.87 out of 5 average rating, 259 reviews

Wonderful Casa Idilio Cortona

AnnaRating, 5 stars2 weeks ago
Perfectly located apartment in old town - with a gorgeous terrace to enjoy some peace outdoors. Simone was most helpful and kind with his instructions and brought me coffee for the moka when I asked was there any coffee. Excellent restaurants and bars nearby. It was a wonderful weekend medieval festival in Cortona - so memorable. Grazie
Guest favourite
Holiday home in Faella
4.93 out of 5 average rating, 111 reviews

Appartamento storico Il Prato a Castelfranco

BettinaRating, 5 stars1 week ago
Die Unterkunft war für uns als Familie mit 3 Kindern ein absoluter Traum. Die Kombination aus modernen Annehmlichkeiten und liebevoll erhaltenen alten Elementen verleiht dem Haus einen ganz besonderen Charme. Man spürt, dass hier mit viel Geschmack und Sorgfalt renoviert wurde – alte Balken, Türen oder Details aus vergangenen Zeiten treffen auf zeitgemäßen Komfort. Die Ausstattung ließ keine Wünsche offen. Traumhafter Pool, wunderschöne Außenanlage. Zudem viele Extras wie Tischfußball, Tischtennis, Bälle, Badminton …. Und vieles mehr. Da kommt keine Langeweile auf.
Superhost
Holiday home in Asciano
4.87 out of 5 average rating, 101 reviews

Dimora di fascino Crete Senesi

TaraRating, 5 stars1 week ago
We had the most wonderful time here, the host was very kind snd helpful, we even met a few of the neighbours, all really friendly and helpful. The views and peacefulness of this house/area made it so special. Waking up to birdsong and roosters everyday. Everything was perfect, thank you.
Guest favourite
Holiday home in Porto
4.95 out of 5 average rating, 130 reviews

La Dimora del Lago - Lake views Tuscany and Umbria

MurrayRating, 5 stars1 day ago
Jan's place could not have been better! As advertised..and even better..and Jan was incredibly responsive to everything..INCLUDING being proactive before checkin. She anticipated everything and even when I had one question, she was immediately responsive. Of all my Air Bnb experiences, this was probably my best. She made local recommendations for restaurants, stories and services...all turned out to be accurate. We met Jan and (her husband Emilio--a Doctor--and good to know) and felt more like good friends in their home rather than "tenants." And as a bonus, Jan has researched her property history and has documentation to prove that Leonardo DaVinci -that one--had a role in the areas development. Just a nice touch. Am VERY happy.
Top guest favourite
Holiday home in Loro Ciuffenna
4.93 out of 5 average rating, 30 reviews

"Gelso" (Mulberry) 2/4p, pool, garden, view

AnnaRating, 5 stars1 week ago
Wir hatten einen wunderschönen Aufenthalt! Infos und Checkin waren durch Simone super einfach. Das Anwesen ist wunderschön! Der tolle Pool und das kühle Haus taten sehr gut. Ich kann es zu 100% weiterempfehlen!
Top guest favourite
Holiday home in Rignano sull'Arno
4.89 out of 5 average rating, 345 reviews

Holiday Toscany nello Strettoio

CamillaRating, 5 stars1 week ago
Absolutely beautiful air bnb. The views and surroundings are breathtaking, we loved swimming in the pool whilst looking over the Italian countryside. Leonardo was a great host, always responded quickly and made us feel welcome. We will definitely come back for another stay.

Holiday home rentals with a patio

Superhost
Holiday home in Castelfranco di sopra
4.74 out of 5 average rating, 39 reviews

Casa nel cuore della Toscana

OvidiuRating, 5 stars1 month ago
Foarte frumoasă locatia si peisajul, gazda deosebit de receptiva si prietenoasa, mi-a facut o deosebită placere sa-i cunosc si sa ma bucur de priveliștea mirifică, recomand tuturor.
Top guest favourite
Holiday home in Cantagallina
5 out of 5 average rating, 48 reviews

Il Tiglio, two pax flat between Umbria and Tuscany

AyeshaRating, 5 stars3 weeks ago
Stefano and his family are amazing hosts with everything you need. The space was clean and tidy with a great large pool to swim in whenever you want. Well equipped and great recommendations for site seeing , wine etc. would absolutely recommend and stay again.
Top guest favourite
Holiday home in Chianni
5 out of 5 average rating, 42 reviews

5*Casa Serena,Fab 1 bed with aircon,parking garden

RobertRating, 5 stars3 days ago
Great place to stay to sample Tuscan village life. Only Walking distance for several very good restaurants in an idyllic setting. Very informative and welcoming hosts who have an abundance of information to share in order to make your stay more complete .
Superhost
Holiday home in Ulignano
4.72 out of 5 average rating, 18 reviews

★ Relaxing apartment & stunning view of Tuscany ★

Anna-LenaRating, 5 stars10 months ago
Wir waren schon zum zweiten Mal dort und es war wie auch schon beim ersten Mal einfach nur perfekt. Diegos Anwesen ist wunderschön mit Blick auf San Gimignano, es ist ruhig und sehr idyllisch sodass man richtig gut abschalten kann. Das Apartment war super, ist gut ausgestattet mit allem was man braucht. Wir haben uns sehr wohl gefühlt und würden uns freuen nächstes Jahr ein drittes Mal zu kommen. Danke an Giorgia für die gute Kommunikation und den flexiblen Check-In.
Top guest favourite
Holiday home in Chianni
5 out of 5 average rating, 19 reviews

Villa Sottosopra - Il Limone

TinaRating, 5 stars5 days ago
Wir hatten eine wundervolle Zeit bei Lena. Die Apartments sind sehr hochwertig ausgestattet und der Blick beim Frühstück über die Toskana ist einfach atemberaubend schön. Wer die Chance hat bei Lena und ihren geliebten 4 Beinern zu übernachten - wird sich gleich wie zu Hause fühlen und eine wunderbare , ganz besondere Zeit haben, sodass man am Ende gar nicht mehr abreisen möchte.
Guest favourite
Holiday home in Certaldo
4.93 out of 5 average rating, 15 reviews

La Selva , Country house, 130 mq, Stunning views

LindaRating, 5 stars1 month ago
Verblijven bij Carmine is top. Wij zijn een maand (half april / half mei) bij Carmine en Alessandra in Certaldo geweest en dat kunnen we iedereen aanraden. Niet alleen de ontvangst ( in ons geval heel laat) was ontzettend hartelijk maar gedurende ons hele verblijf hebben we ons heel comfortabel gevoeld, deze host staat altijd open voor vragen, is pro actief met geven van informatie, tips over van alles zoals waar het leuk / lekker/ mooi is om te bezoeken. Daarnaast is het huis hartstikke fijn, het ligt geweldig in het Toscaanse heuvelland, tussen de wijn en olijf boeren, fijne bedden (vinden wij altijd belangrijk vooral als je er langer verblijft) en echt goede wifi wat voor ons belangrijk was om zo ook van hieruit te kunnen werken. De locatie is perfect. Je zit dichtbij Florence, Siena, Pisa, en vele bijzondere andere dorp/stadjes die het bezoeken meer dan waard zijn. De maand was te snel voorbij! Als we nog eens Toscane bezoeken zeker weten bij Carmine en Alessandra!
Superhost
Holiday home in Montaione
4.84 out of 5 average rating, 32 reviews

Podere Sant'Anna | Casa Fiordaliso

KamilaRating, 5 stars3 weeks ago
Cudowne miejsce, wszystko co potrzeba na miejscu. Widok z balkonu najlepszy na świecie. Byliśmy już w Toskanii, ale do tego miejsca wrócimy z wielką chęcią.
Guest favourite
Holiday home in Gaiole in Chianti
4.96 out of 5 average rating, 28 reviews

The Piccola Villa of Borgo Argenina

MeghanRating, 5 stars4 weeks ago
This was our favorite place we stayed in Italy and we went to three other locations. The view is unbeatable and so much to do nearby. We went to a few wineries and ate at Malborghetto (Highly recommend for an authentic experience and small town feel!). We hope to come back! Communication with hosts was great. amenities such as the pool, breakfast, the kitchen, were awesome. Thanks so much for a wonderful stay!

Holiday home rentals with a washing machine and dryer

Top guest favourite
Holiday home in Serravalle Pistoiese
4.93 out of 5 average rating, 45 reviews

Il Glicine @ Casa d'Olival

PatrickRating, 5 stars8 months ago
Gioia’s little piece of Tuscan paradise exceeded all expectations. The apartment was lovely, the scenery gorgeous and the pool perfect for lounging amongst the lavender and olive trees, not to mention hanging out with Wolfy. Do not miss an opportunity to take the pasta making class with Graziella as she helped us craft one of the best Italian meals we’ve had! This was one of the highlights of our weeks in Europe and we can’t wait to return.
Top guest favourite
Holiday home in Figline e Incisa Valdarno
5 out of 5 average rating, 43 reviews

Casa colonica nel verde con piscina Solatìo

ArnoRating, 5 stars2 weeks ago
We absolutely loved our stay at Marco’s beautiful place! The apartment is stylish, comfortable, and fully equipped with everything you might need. The swimming pool and stunning views of the Tuscan countryside created the perfect setting to relax, read a book, or enjoy a glass of wine. What truly made our stay exceptional, though, was Marco himself—his warm personality and genuine hospitality made us feel incredibly welcome. We highly recommend staying at Marco’s and would love to come back someday!
Superhost
Holiday home in Crespina
4.91 out of 5 average rating, 11 reviews

Poggio al Casone - Barrique basic apartment

DanielRating, 5 stars6 days ago
Wundervolle Unterkunft mit jeglichen Möglichkeiten. Von eigens gestalteter Selbstversorgung bis hin zur Buchungsmöglichkeit aller Services für die Rundum-Versorgung. Alles vorhanden was man für einen sehr guten Entspannungsurlaub benötigt. Wir werden nochmal vorbeikommen.
Guest favourite
Holiday home in Centro Storico
4.91 out of 5 average rating, 275 reviews

Melarancio Residence

TasneemRating, 5 stars3 weeks ago
We enjoyed our stay at this apartment. Having an elevator was a blessing on days we were exhausted and air conditioning in every room meant we didn’t have to melt the few days we had really hot weather. Location is super convenient with the Mercato Centrale, Firenze SMN station, and the Medici chapel just around the corner from us. The grocery store downstairs was well stocked and there’s also a dollar store, pharmacy, and gym nearby.
Superhost
Holiday home in Paciano
5 out of 5 average rating, 3 reviews

part of luxury farmhouse - airco, infinity pool

ViktorRating, 5 stars8 months ago
I recently had the pleasure of staying at Villa Lidia, and I can confidently say it was one of the best travel experiences I've ever had! From the moment we arrived, we were greeted with warm hospitality and stunning views that took our breath away. The location is simply perfect—a peaceful retreat in the middle of an olive yard. The recommendations provided by our host were spot-on, guiding us to hidden gems that we would have missed otherwise. One of the highlights of our stay was the pool area, where we spent sun-soaked afternoons relaxing and enjoying the peaceful ambiance. It was the perfect way to unwind after a day of exploration. Overall, Villa Lidia exceeded all our expectations. Whether you’re looking for a romantic getaway or a family retreat, this is the place to be! I can’t recommend it highly enough, and I can't wait to return to this little slice of paradise in Umbria. Thank you for an unforgettable stay!
Top guest favourite
Holiday home in Centro Storico
4.98 out of 5 average rating, 93 reviews

Two floors of BLUE in the center of Florence

VanessaRating, 5 stars2 weeks ago
Claudia was the best host I have had the pleasure of experiencing, her place is amazing and she was wonderful. I greatly appreciate her being flexible with checking and being so kind with my family. Please stay with her, I felt right at home and so will you :)
Guest favourite
Holiday home in Centro Storico
4.92 out of 5 average rating, 167 reviews

TOSCANELLA STUDIO QUARZO

MandoRating, 5 stars2 weeks ago
This place was awesome!! Perfect location close enough to everything but far enough from all the noise.. it was just right for me and my wife I highly recommend it!!
Guest favourite
Holiday home in Casole d'Elsa - Siena
4.91 out of 5 average rating, 23 reviews

Elegante Agriturismo immerso nella natura, Aria

PatriziaRating, 5 stars2 months ago
Wir hatten über Ostern einen Tour durch die Toskana geplant und wurden von Romina direkt sehr herzlich empfangen. Die Unterkunft liegt sehr abgelegen und ist mit dem Auto über Feldwege erreichbar. Durch die Beschreibungen von Romina konnten weiter das Gelände aber direkt finden. Wir sind mit dem E-Auto angereist und konnten unser Auto problemlos vor Ort laden. Von dort haben wir Siena, San Gimignano und Volterra besichtigt, was alles zwischen 30-50 Minuten mit dem Auto entfernt liegt. Ansonsten hatten wir auch dort eine schöne Zeit durch die Ruhe vor Ort. Romina und Riccardo haben eine Olivenplantage und stellen eigene Produkte her. Darunter nicht nur Olivenöl, sondern auch Honig und Ätherische Öle. Romina hat uns alles gezeigt und wir durften Öl und Honig probieren. Wir haben direkt auch Ölivenöl und Honig gekauft, um es mit nach Hause zu nehmen. Wir würden jeder Zeit wieder kommen. Vielen Dank für den schönen Aufenthalt!

Destinations to explore

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