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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 - Apartment with balcony

Marcel SarahRating, 5 stars1 week ago
Antonella, Andreas and not to forget Lullu are perfect and so relaxed hosts. They sweetened our mornings with fresh bread, croissants, and coffee. The apartment is well equipped and of high quality. We felt very comfortable right away. The garden invites you to linger and is particularly well maintained. Thank you for this special stay!
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
Authentic working home with great views. Lovely location secluded and close to hiking route makes it nice to have a dog with you.
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 Siena
4.85 out of 5 average rating, 78 reviews

"Lisa" apartment with fireplace

BerinRating, 5 stars3 weeks ago
The place is just breathtaking. Lisa was very sweet and had prepared us a little gift. I would definitely recommend! There are lovely dogs which we got used to so much 🥹🧡
Guest favourite
Holiday home in Faella
4.93 out of 5 average rating, 112 reviews

Historic apartment Il Prato in Castelfranco

AnneRating, 5 stars1 day 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 stars1 week 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

Charming home 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 nel 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, an ancient farmhouse in the heart of Tuscany

LauraRating, 5 stars1 week ago
We had a great stay and Frederic was always reachable. The house and garden are beautiful and it’s perfect for 4 people.
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 stars6 days 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, 16 reviews

Casa Monte

AdamRating, 5 stars10 months ago
Umbria gem. This place was beautiful, clean, comfortable and peaceful. highly recommend it for an Italy getaway we will be back. Gabriele was a kind and welcoming host.
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
We went there for the second time and it was just perfect as the first time. Diego's property is beautiful overlooking San Gimignano, it is quiet and very idyllic so you can really unwind. The apartment was great, is well equipped with everything you need. We felt very comfortable and would love to come a third time next year. Thanks to Giorgia for the good communication and flexible 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

Farmhouse in the countryside with swimming pool 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 RUBY STUDIO

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 Luxury Stay Umbria/Tuscany/Lake Trasimeno

DanielRating, 5 stars5 months ago
We stayed here over the Christmas holidays and enjoyed our stay, the large living and dining area is very cozy and the fireplace has created a wonderful winter atmosphere. The amenities of the bathrooms, the rooms and the kitchen are wonderful, modern and stylish. The house is ideal for larger groups, with no one having to give up a retreat. The location is very quiet and the view of the surrounding hills magnificent. At the same time, the house is strategically located and within an hour you will find great excursion destinations (Perugia, Assisi, Todi, Montepulciano...). Our host was always available and we were warmly welcomed. We will be happy to come back!
Guest favourite
Holiday home in Poggibonsi
4.92 out of 5 average rating, 53 reviews

App.Cavallo - Megognano,2/A

MattiaRating, 5 stars4 days ago
We stayed at the Flaminia property with our 13-year-old daughter and we had a great time. Flaminia is friendly, attentive and very helpful. The beds are really very comfortable and their bio lake is a fabulous surprise. The apartment was in line with the photos and it was a wonderful stay. Thank you, Flaminia 🥰
Guest favourite
Holiday home in Montespertoli
5 out of 5 average rating, 7 reviews

Rondini Blu Vacation Home - Uva Apartment

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

The fresco of the Macci

NenadRating, 5 stars6 days 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

Entire historic villa with private pool in Tuscany

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