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Holiday home rentals in Montalcino

Find and book unique holiday home rentals on Airbnb

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Popular amenities for holiday home rentals in Montalcino

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 Cortona
4.98 out of 5 average rating, 46 reviews

La Pergola | Farm House with fantastic view

Rasmus RudRating, 5 stars11 months ago
Autentisk fungerende bolig med fantastisk udsigt. Dejlig placering ugeneret og tæt på vandrerute gør det dejligt at have hund med.
Guest favourite
Holiday home in Cortona
4.87 out of 5 average rating, 260 reviews

Wonderful Casa Idilio Cortona

AnnaRating, 5 stars3 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 Siena
4.85 out of 5 average rating, 78 reviews

"Lisa" apartment with fireplace

AlexRating, 5 stars4 days ago
Der Aufenthalt bei Lisa war traumhaft. Es war alles sogar noch schöner als auf den Fotos. Die Unterkunft war sehr geräumig und sehr ordentlich. Die Umgebung war traumhaft schön. Wir haben Lisa jeden Tag gesehen und konnten uns jederzeit an sie wenden. Der Pool, der Garten alles war einfach nur wunderschön und die Tiere haben uns den Aufenthalt noch versüßt. Wir würden jedem die Unterkunft bei Lisa empfehlen, denn so etwas ist wirklich einzigartig und sehr selten. Wir kommen gerne wieder!
Guest favourite
Holiday home in Faella
4.93 out of 5 average rating, 112 reviews

Appartamento storico Il Prato a Castelfranco

AnneRating, 5 stars2 days ago
Fab pool! Very comfortable accommodation with friendly host. We really enjoyed our family time there. Train station 10 minutes away with free parking. Very good coop near also
Top guest favourite
Holiday home in Bolsena
4.98 out of 5 average rating, 172 reviews

The view with a room - Piazza dei Monaldeschi

EricaRating, 5 stars2 weeks ago
Our stay at Giulio & Emanuela’s place was truly magical. Giulio was very proactive and responsive with giving us directions and instructions on how to get there. They were always there for us if needed and extremely friendly, welcoming, and helpful. Could not rave about this gem more. The place and the surrounding neighborhood are something special, and I hope to be back again someday!
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.
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

Top guest favourite
Holiday home in Orvieto
4.99 out of 5 average rating, 95 reviews

Casa Isla, near Orvieto, amazing views + pool

GeorgiRating, 5 stars1 month ago
We had wonderful stay at Casale Zeno. The pristine environment is exactly what we needed and the beautiful sceneries surrounding the property were divine. Jo and Tony are very friendly hosts and it was pleasure staying at their place. We really appreciate all the small details provided in the accommodation along with the super comfortable mattress and pillows. The house is a perfect base for exploring Orvieto and the fantastic region around it. We would happily come back and recommend it. Thank you for a magical stay!
Superhost
Holiday home in Torrita di Siena
4.83 out of 5 average rating, 18 reviews

Pian'D'olmo, antico casale nel cuore della Toscana

ClaudiaRating, 5 stars3 weeks ago
La estadía en esta casa fue realmente espectacular. Todo precioso, limpio, práctico e incluso mejor que lo que se ve en las fotos. Además la casa estaba equipada con todo lo necesario y hasta cosas extras como para cocinar, descansar, abrigarse y todo lo imprescindible para el baño y el resto de los espacios. Pasamos una increíble estadía con nuestra familia, fue el cierre ideal del viaje a Italia. Un lugar maravilloso con muchísima tranquilidad y cerca de muchos pueblos hermosos que visitar. No tuvimos ningún problema con el hospedaje y aún así Frederic estuvo siempre atento a que estuviéramos cómodos. Recomiendo este hospedaje en un 100%. De los mejores en que me he quedado. Muchas gracias por todo Frederic. De verdad estuvo todo impecable.
Top guest favourite
Holiday home in Cantagallina
4.96 out of 5 average rating, 45 reviews

Il Cipresso, one bedroom apartment near Trasimeno!

GrahamRating, 5 stars1 week ago
An absolutely wonderful place, this was the best Air-BNB we have ever stayed in. The owners are lovely and put so much love and attention to detail into every aspect, not just the property but the gardens too. We felt extremely welcome and comfortable right from the start and throughout our stay. The thoughtful arrangement of properties and trees and hedges ensures all guests have privacy when they want it but at the same time easy access to all facilities and to the owners. The pool was spotlessly clean and we enjoyed using it most days between trips out and the thoughtful provision of garden games made our stay the best. Rosi, Stefano and Valentina are the perfect hosts, we would love to return and highly recommend this fabulous place.
Superhost
Holiday home in Greve in Chianti
4.9 out of 5 average rating, 20 reviews

Cuculo - Rifugium

KlioRating, 5 stars2 months ago
Beautiful apartment in the countryside. Spacious and clean. The access by car was a little difficult but definitely recommended.
Guest favourite
Holiday home in Umbertide
5 out of 5 average rating, 17 reviews

Casa Monte

SydRating, 5 starstoday
Gabriele was a great host. The property has a lot of character and had several great spaces to experience with friends. Highly recommend.
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.
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!
Superhost
Holiday home in Radda in Chianti
5 out of 5 average rating, 31 reviews

Tuscany Country House, Central Chianti, Pano Views

KyleRating, 5 stars1 month ago
We found Peggy’s place to be the perfect spot for exploring Tuscany. The instructions made it for easy to find & only a few short minutes drive from Panzano where we had lunch at Dario’s (a must in our opinion). Also highly recommend Montese Cooking Experience in San Gimignano.

Holiday home rentals with a washing machine and dryer

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!
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.
Guest favourite
Holiday home in Centro Storico
4.93 out of 5 average rating, 179 reviews

TOSCANELLA STUDIO RUBINO

BilbaoRating, 5 stars1 month ago
We had an excellent stay at this apartment in Florence! The space is simple yet very practical, comfortable, and equipped with everything needed. The building is old, charming, and authentic — a true piece of the city’s history. Having an elevator was a big plus. The apartment is cozy, well laid out, and perfect for relaxing after a day of exploring. The neighborhood is wonderful, full of life, with many art galleries, bars, and cozy cafes. The neighbors are friendly and the street is especially beautiful — ideal for peaceful walks. Everything combined made our experience in Florence truly special. Highly recommend!
Superhost
Holiday home in Mugnano
4.69 out of 5 average rating, 42 reviews

Best Luxery Stay Umbria/Tuscany/Lago di Trasimeno

DanielRating, 5 stars5 months ago
Wir waren über die Weihnachtsferien hier und haben unseren Aufenthalt sehr genossen, der grosse Wohn- und Essbereich ist sehr gemütlich und der Kamin hat eine wunderbare winterliche Stimmung geschaffen. Die Ausstattung der Bäder, der Zimmer und der Küche ist wunderbar, modern und stilvoll. Das Haus eignet sich ideal für größere Gruppen, wobei niemand auf einen Rückzugsort verzichten muss. Die Lage ist sehr ruhig und die Aussicht auf die umliegenden Hügel herrlich. Gleichzeitig liegt das Haus der strategisch und innerhalb einer Stunde in jegliche Richtung findet man tolle Ausflugsziele (Perugia, Assisi, Todi, Montepulciano…). Unser Gastgeber war immer zu erreichen und wir wurden herzlich empfangen. Wir kommen gerne wieder!
Guest favourite
Holiday home in Poggibonsi
4.92 out of 5 average rating, 53 reviews

App.Cavallo - Megognano,2/A

MattiaRating, 5 stars5 days ago
Abbiamo soggiornato presso la struttura di Flaminia insieme a nostra figlia di 13 anni e ci siamo trovati molto bene. Flaminia è cordiale, attenta e molto disponibile. I letti davvero molto comodi e il loro bio lago una favolosa sorpresa. L’appartamento era in linea con le foto ed è stato uno splendido soggiorno. Grazie Flaminia 🥰
Guest favourite
Holiday home in Montespertoli
5 out of 5 average rating, 7 reviews

Casa Vacanze Rondini Blu - Appartamento Uva

ErikaRating, 5 stars2 months ago
A perfect Tuscany stay. We really enjoyed our stay. Thank you!
Superhost
Holiday home in Centro Storico
4.86 out of 5 average rating, 106 reviews

L'affresco dei Macci

NenadRating, 5 stars1 week ago
Stella’s apartment is in the perfect location. This was our second time in Florence and we knew we wanted to stay in Santa Croce for the incredible location and the local feel. She was very accommodating and let us check in late and even held my luggage during checkout. 10 stars for being a great hostess! The frescoes are very interesting and give you the feeling that you’re in a truly historic place. The 2 bedrooms had everything we needed for my wife and I and our young children. The bathroom and shower have been fully renovated and look great. The location is perfect and is just outside the hustle and bustle of the duomo and palazzo Vecchio. Also, we had really enjoyed a small local pizzeria called Malborghetto, and as soon as we booked, we realized it was right across from the apartment! Do try it out if you get a chance, it’s run by locals and is some of the best pizza you’ll ever have. Also, the osteria right next door has amazing pasta. You can’t go wrong with Stella’s apt
Top guest favourite
Holiday home in Noce
5 out of 5 average rating, 21 reviews

Intera Villa storica con piscina privata inToscana

BrunoRating, 5 stars4 months ago
Niccolo was a great host from reservation to check out... in fcat, even after he kept giving us recommendations for the rest of our short trip in Tuscany. The property has a picture-perfect view and this was in January. I can hardly imagine how beautiful it would be in summer with the vines.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montalcino
  6. Holiday home rentals