Some info has been automatically translated. Show original language

Family-friendly holiday rentals in Montalcino

Find and book unique family-friendly homes on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for Montalcino family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars4 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 119 reviews

Villa in Montepulciano with Pool

MosesRating, 5 stars4 months ago
Alex, u show such hospitality to our family!! We love how well u maintained the place. The view from our hotel brings smile to my face every morning! It’s spectacular. I’ll definitely come back! Hope the price is reasonable the next time 🥰
Superhost
Home in Gaiole In Chianti
4.86 out of 5 average rating, 250 reviews

Charming estate with views

MoritzRating, 5 stars3 months ago
We loved Bernardino's place. It was super cozy, the garden and whirlpool were amazing. The kitchen had everything we needed. And Bernardino was super helpful with tips and answers to all our questions. Highly recommend if you're looking for a remote place to enjoy Tuscany.
Guest favourite
Villa in San Casciano in Val di Pesa
4.94 out of 5 average rating, 162 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

AmandaRating, 5 stars4 weeks ago
Incredible stay at Beatrice’s place. From booking to exit she had helped my group and I plan our stay in Tuscany finding wineries and vineyards to explore. She was so kind and pleasant to work with I would suggest her place to anyone! The kitchen was cozy and perfect for our group to spend time in while at the bnb. Every room was exactly as described. Perfect stay!
Guest favourite
Cottage in Geggiano
4.99 out of 5 average rating, 126 reviews

Villa di Geggiano - Guesthouse

GabrielRating, 5 stars1 month ago
Vila Di Geggiano was everything we were expecting it to be and more. We simply loved the place, quiet and very comfortable, set in the middle of a beautiful Toscana. The guest apartment is located by the side of the Main House, a historical summer palace with a deep history behind it. Andrea, our host, gave us a personal tour of the main house, filled with great stories about his ancestors. The house has been in Andrea´s family since the 1500s! If you are looking to spend some quiet days enjoying the great food and wine of Toscana in a relaxed, unique and comfortable space, Vila di Geggiano is a great destination for you.
Guest favourite
Cottage in Castell'azzara
4.98 out of 5 average rating, 129 reviews

Your Private Tuscan Retreat

IliaRating, 5 stars2 months ago
A beautiful, peaceful spot in the heart of Tuscany - perfect for a relaxing getaway! Riccardo and Kate are wonderful hosts who made everything easy and made us feel right at home. The house is cozy and well-equipped with everything you could need, from a comfy bed and a fully stocked kitchen to a sauna and an amazing open-air hot tub. Also, one of the bonuses of this location is very low air pollution, so stargazing at night was a real highlight of our trip. Would definitely recommend for anyone looking to unwind and enjoy the beauty of Tuscany.
Guest favourite
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

PeterRating, 5 stars3 months ago
Very nice and clean appartment in a very quiet area. Only Met Gaston shortly since we were out all day visiting Tuscany with friends, But he was very Friendly. Will definitely come back
Guest favourite
Farm stay in Figline Incisa Valdarno
4.94 out of 5 average rating, 349 reviews

Romantic in bioagriturismo Florence

SimonaRating, 5 stars1 week ago
Fantastic experience from Francesca who created a small oasis of well-being and tranquility in a wonderful place. Perfect for several days of relaxation and as a base to discover the territory and its delicacies. Great breakfast basket, also perfect for celebrating special occasions thanks to the extra amenities such as the outdoor bathtub and massages that were a real treat! Plus a very comfortable bed, the bathroom is spacious, and the temperature is always perfect in the rooms. We were greeted with kindness and extreme availability to meet if we did not anticipate the needs of our infant, in fact we were provided with a crib and a bathtub for the bath. I highly recommend it and hope to stay with you again soon! Thank you Simona, Michele and little Ernesto🤗

Family- and pet-friendly home rentals

Superhost
Apartment in Sasso Pisano
4.78 out of 5 average rating, 187 reviews

La Maison di Monica & Simona

MaximeRating, 5 stars2 months ago
Monica is very welcoming. The value for money is very good. Be careful if you have small children because there are slightly steep stairs to access the accommodation.
Guest favourite
Condo in Cortona
4.98 out of 5 average rating, 129 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

John MarkRating, 5 stars3 weeks ago
We had an incredible stay at Clara's property in Cortona! The highlight of our trip was definitely the visit to the farm, which was not only fun but also deeply meaningful. We loved learning about the local way of life. Our host, Clara, was warm, welcoming, and extremely helpful throughout our stay. They went above and beyond to ensure we felt at home and had everything we needed. The property itself was clean, comfortable and well-located. We would highly recommend to anyone looking for an authentic and unforgettable experience in Cortona. Grazie mille, Clara for sharing your little slice of heaven with us!
Guest favourite
Apartment in Montiano, Magliano in Toscana
4.98 out of 5 average rating, 44 reviews

Poggio Bestiale holiday home

ChiaraRating, 5 stars6 months ago
The accommodation is as described and perfect for a relaxing holiday. Great location to reach the Argentario and at the same time enjoy the return of a silence and a fantastic view. The apartment is very nice and clean, Denise is a superlative host, we were very very satisfied.
Superhost
Home in Gaiole in Chianti
4.8 out of 5 average rating, 100 reviews

loft in the heart of Tuscan Chianti

CharlotteRating, 5 stars4 months ago
We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.
Guest favourite
Home in Subbiano
4.99 out of 5 average rating, 78 reviews

Romantic cosy flat - Toscana Italy

DavidRating, 5 stars5 months ago
This was exactly what we were looking for. Very peaceful and private with beautiful views. Lots of wonderful villages to visit and explore within a 30 minute drive. Norma made some great reservations for our anniversary dinner as well as a couple of great wine tours. She also gave us recommendations of which villages were best to visit and what to do there. We highly recommend doing the cooking lessons with her family. They are such a nice family and were very eager to show us how to cook a traditional Tuscan meal. Grandma really is an amazing cook. They even sat with us as a family to share what we had cooked. We have been to many AirBnB’s and Norma has been our best host by far. We would go back the next time we visit Tuscany. Dave and Liz
Superhost
Farm stay in Montepulciano
4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

SylvanaRating, 5 stars5 months ago
The only thing I could say negative is the lack of lighting for the kitchen and dining room. For the rest everything is perfect if you like the countryside decor:-)
Guest favourite
Condo in Asciano
5 out of 5 average rating, 162 reviews

Pink as the sunset sky

하늘Rating, 5 stars4 months ago
Famous small towns around Tuscany are expensive, but this is a place where you can fully enjoy the natural scenery of Tuscany at a reasonable price. The host was very friendly and the house was a very nice place to get a hands on experience of the farmhouse. It's an old brick house, but the antique interior and natural scenery were great.
Guest favourite
Apartment in Caminino
4.91 out of 5 average rating, 161 reviews

Pieve di Caminino Historic Farm

SusannaRating, 5 stars1 month ago
the structure is a dream... we stayed in Foresteria, better than the photos!!! Perfect place for those looking for tranquility with respect and in full contact with nature. Emiliano wonderful host, he made us find the fireplace on, he allowed us to bring our dogs and leave them free in his beautiful estate and gave us many tips on activities to do nearby... we can't wait to come back!!

Family-friendly home rentals with a pool

Superhost
Apartment in Cortona
4.6 out of 5 average rating, 5 reviews

Medieval Cottage near Cortona

AnneRating, 5 stars43 months ago
Words can’t describe how beautiful this little restored village is - if you are seeking for a tasteful arranged place where you are all by yourself, surrounded by pure nature and a few other guests (that respect your privacy) this is where you should go. Highly recommended!!
Guest favourite
Apartment in Gaiole In Chianti
4.76 out of 5 average rating, 21 reviews

Idyllic with shared pool in the heart of Chianti

GuidoRating, 5 stars6 months ago
Heidi's apartment is situated in a larger complex on the outskirts of the village, just a short walk from the town center where you can find a church, a mini supermarket, bars, and a popular restaurant that is always fully booked. The village is ideally located in the heart of Chianti, making it a perfect starting point for exploring the region. You can drive along one of the scenic, winding roads to a wine tasting event, enjoy a bike ride through the picturesque countryside, or visit nearby cities like Siena or Florence (Firenze). One of the highlights of the apartment is the spacious swimming pool (1.35 m deep), which is perfect for cooling off during the hot summer days, especially if you have kids. The apartment itself is well-equipped, ensuring a comfortable stay. Communication with Heidi is easy and friendly. She provides detailed information on the check-in and check-out procedures, as well as instructions for using various amenities in the complex. We enjoyed our stay!
Guest favourite
Villa in Ortignano Raggiolo
4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars4 months ago
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars4 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Superhost
Villa in Talla
4.91 out of 5 average rating, 22 reviews

Lovely villa heated outdoor pool & tennis court

LoriRating, 5 stars4 months ago
The villa exceeded our expectations. It was exceptionally clean and well cared for. Excellent amenities. Beautiful surroundings with olive and lemon trees. Cute little village nearby with an excellent restaurant. The host was very responsive. We had a bit of trouble finding the place but that might be more us than the directions. You definitely need a rental car Thank you for an amazing stay
Guest favourite
Apartment in La Felce
4.98 out of 5 average rating, 107 reviews

La Felce Country House

GarrettRating, 5 stars5 months ago
Cristina is the ultimate host! Everything was immaculate and set up for us. We traveled with two young kids, and she was proactively prepared with a crib & high chair. She also had amazing recommendations and answered any questions for us. Led us to a spectacular sunset winery in the hills. The premise has stunning views and hanging poolside in the mountains, was just what the doctor ordered. Highly recommended and makes you feel like family!
Guest favourite
Farm stay in Pienza
4.93 out of 5 average rating, 169 reviews

Agriturismo Palazzi del Papa Val d 'Orcia Pienza

LeslieRating, 5 stars3 months ago
Nice agriturismo, very chill place and beautiful surroundings
Superhost
Home in Cortona
4.92 out of 5 average rating, 26 reviews

Beautifully restored villa with private pool

RoxarnaRating, 5 stars5 months ago
Thank you for allowing us to stay at your wonderful accommodation. This was the best place to celebrate my 50th birthday. What wonderful accommodation, facilities and the surrounds of Tuscany. Thank you for your lovely hospitality and making us feel so welcome. Roxy

Quick stats about holiday rentals that are family-friendly in Montalcino

  • Total rentals

    480 properties

  • Nightly prices starting at

    $64 AUD before taxes and fees

  • Total number of reviews

    12K reviews

  • Pet-friendly rentals

    290 properties allow pets

  • Rentals with a pool

    250 properties have a pool

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

Destinations to explore