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Holiday Homes in Montalcino

Find and book unique holiday homes on Airbnb

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Popular amenities for Montalcino holiday homes

Family-Friendly holiday homes

Guest favourite
Holiday home in Passignano sul Trasimeno
5 out of 5 average rating, 25 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!
Top Guest favourite
Holiday home in San Donato In Poggio
4.98 out of 5 average rating, 140 reviews

Chianti Penthouse with panoramic View & Pool

AntoniaRating, 5 stars1 month ago
Giada's penthouse apartment was the perfect spot for a relaxing stay in Tuscany. Accessible to so many Chianti vineyards, we only wish we'd had more time staying there to explore, and less rainy weather, to enjoy the on site amenities like the pool and the two balconies more. She also gave us recommendations for the area which were super helpful! We would happily stay again.
Guest favourite
Holiday home in Faella
4.93 out of 5 average rating, 112 reviews

Historic apartment Il Prato in Castelfranco

AnneRating, 5 stars4 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 Siena
4.97 out of 5 average rating, 60 reviews

Apartment in historic Villa in Siena_"LE CONTRADE"

PaulRating, 5 stars1 month ago
Located a long walk or very short (5 min) drive outside of Siena. Upon arrival, we had a little difficulty locating the apartment parking lot (small entrance off street), but once we knew where it was it was very easy after that. The apartment was wonderful, big for us, and cozy. Cristina was very communicative with us, and recommended many wineries and restaurants in Siena. We really enjoyed our stay and would stay here again.
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 Loro Ciuffenna
4.95 out of 5 average rating, 37 reviews

"Loggiato" (Porch) 2/4p, terrace, pool, garden

MaximilianRating, 5 stars1 week ago
We had a wonderful stay! The place was absolutely perfect – clean, beautifully furnished, and equipped with everything we needed. The peaceful location in the middle of the Tuscan countryside was ideal for relaxing. Communication with the host was smooth and friendly. We’d love to come back – 100% recommended!
Top Guest favourite
Holiday home in San Gimignano
4.92 out of 5 average rating, 243 reviews

Appartamento Margherita Tuscan home

JuleRating, 5 stars1 week ago
The stay was very pleasant. The view from the balcony was beautiful and the location very central.
Top Guest favourite
Holiday home in Rignano sull'Arno
4.89 out of 5 average rating, 345 reviews

Holiday Toscany nel Strettoio

CamillaRating, 5 stars2 weeks 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.
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.
Top Guest favourite
Holiday home in Umbertide
5 out of 5 average rating, 16 reviews

Casa Torre

JoannaRating, 5 stars8 months ago
We had a magical stay at this house! He surroundings are breathtaking and lots of space for my kids to run around and explore the natural beauty. We felt right at home in this house and it was the perfect base for us to go out exploring everyday. We can only hope to return on our future travels.
Superhost
Holiday home in Piegaro
4.67 out of 5 average rating, 3 reviews

Il Forno - 2 bedroom with private poolside terrace

MortenRating, 5 stars11 months ago
we had an amazing time in piagaro,and Thomas gave so mutch information about the Village and a guide around when we arrived. that was really good. he was also a really interesting and reflected man. We had some really good conversations and I would love to come back to his place. I used the cafe every morning for the morning coffee just to take in the atmosphere in the village with the most lovely staff there . LOVELY 😃. truly a special stay for us. we wish them the very best 🥰 Morten with family
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 I Castagni
4.88 out of 5 average rating, 26 reviews

Gorgeous tranquil farmhouse 5 min from Castiglione

BethRating, 5 stars3 weeks ago
Jeremy’s place was lovely, very peaceful location and great to have use of both the garden at the back and the terrace at the front. The kitchen had everything we needed and the bedrooms were comfortable. The whole place remained cool even though it was hot outside. The only downside for us was that you have to exit the house via the stairs at the front to get to the back garden, just a minor point but a bit of a challenge with young kids. Overall we had a wonderful stay and Jeremy was very responsive and helpful. Thank you!
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 stars1 month 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 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.
Superhost
Holiday home in Paciano
5 out of 5 average rating, 3 reviews

part of luxury farmhouse - airco, infinity pool

ViktorRating, 5 stars9 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
4.96 out of 5 average rating, 49 reviews

RED into the heart of Florence

NeilRating, 5 stars1 month ago
Casasafer is a modern AirBnB with all that you need for a memorable stay in Florence. Step out the door, walk for a few mins in any direction, and you'll likely find yourselves in one of Florence's many wonderful must-see places. The duplex apartment we stayed in was very pleasant, opening into a cozy dining room with an adequate kitchen on the side, an open air sit-out for sunny days, and a mezzanine loft with a comfortable large double bed that fit two adults and two lite kids. There was also a sofa-bed in the dining room we could've used. The common basement area is also another zone that one can spend time in, especially if you are a frazzled parent who needs to maybe read a book far from the madding kids. Overall, the sort of place you can always safely recommend. Our special thanks also to Claudia, whose care for the little details like a bit of a snack and a good bottle of local wine to welcome us, and helpful tips for places to visit, food to try, gave our trip a local touch.
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!
Guest favourite
Holiday home in Bagno A Ripoli
4.91 out of 5 average rating, 35 reviews

Studio apartment in the hills near Florence

GreggRating, 5 stars6 days ago
A beautiful place to stay, very clean and Violetta is a gracious host. She provided excellent information about the local area. My mother was raised in Firenze, so we came many times to visit the family. I picked her place because it was close to where my last Italian family lives. And it's far enough from the touristy Firenze to me beautiful and quiet. Violetta even helped me find info on my cousin. What a beautiful stay! Come and enjoy this beautiful Tuscan hillside area!
Guest favourite
Holiday home in Poggibonsi
4.93 out of 5 average rating, 54 reviews

App.Cavallo - Megognano,2/A

XinyiRating, 5 stars4 days ago
Flaminia and Luigi are very welcoming! The view of the place is fantastic. Room is very clean and spacious, we enjoyed our stay here!
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!

Destinations to explore

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