
Family-friendly vacation rentals in Montalcino
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Montalcino
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Montalcino family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi
This was our second time at Il Vichiaccio and I hope it's not the last. In fact, this Airbnb is the entire reason we had Tuscany on our trip itinerary. Beatrice and Massimo are the most wonderful hosts in the world. Besides simply being great people to chat with, they are hospitable in providing some of their homemade wine and eggs. There's nothing more special than relaxing in the hot tub with the vineyard views and walking up the hill to dinner at Il Cavaliere in the castle. Our only complaint is that we did not see the kitty cat this time! She was our favorite host when we visited 3 years ago. Oh well, I guess we'll have to book again soon and try once more :)

Villa in Montepulciano with a Pool
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!

Charming estate with views
We had such a lovely stay at Bernardino’s villa! He greeted us when we arrived and made sure we had everything we needed. The home is very charming and peaceful, and centrally located to explore Tuscany. Would definitely recommend!

The Vichiaccio Villa with Jacuzzi in Chianti
Beatrice was a wonderful host and accommodating of our needs traveling with a two year old. She was very responsive and gave amazing recommendations for places to eat and visit. The location is stunning - even more beautiful than the pictures! Every direction you look has rolling vineyards. We opted to have them cook a special birthday meal one of the nights, and it was delicious. The only small downside is there isn’t a common area to spend time in besides the kitchen (just the layout of the house). We loved it and hope to come back some day!

Villa di Geggiano – Guesthouse
The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!

Your Private Tuscan Retreat
We had a wonderful stay at Riccardo and Kate’s beautiful hide‑away in Tuscany. The place was spotless, thoughtfully equipped and felt both spacious and cosy at the same time. It’s perfectly located, only a five‑minute drive to the lovely town of Castelle Azzara. Waking up to birdsong, spending slow afternoons in the sauna and spa and falling asleep to absolute silence left us completely relaxed. Riccardo and Kate were the perfect hosts - welcoming, attentive and responsive. They really have thought of everything. If you’re looking for peace, comfort, and a real Tuscan escape, this is the place. We 100% recommend to future guests. Grazie mille!

Casa al Gianni - The Simignano Barn
Cristina’s villa was the perfect Tuscan escape for our family. There is much to love…the sweet pigs, the village dogs, the breathtaking views, the peaceful and quiet evenings and mornings, delicious food and beer produced on the farm, AND the most lovely and kind family/hosts. I could honestly go on and on about how much we loved this villa and location. 5 stars all the way! We had our 6 yr old daughter with us and she says it was her favorite place she has stayed on a holiday because of the pigs, ping pong table, swing, and because she had so much fun with the host family children and other guests whom stayed in the other available villas. Also, the big dinner hosted on the last night of our stay was the highlight of our trip! (Tip: make sure to buy some of their products made on the farm….so delicious!)

VILLALADOLCEVITA
Claudia's place is a real gem. We were a family of 8 staying at the villa and we had a great time. The scenery is breathtaking and the space is perfect for a larger family. The grounds of the villa are very well kept and the spa area was amazing. We are already talking about our next trip! Thank you again for a unforgettable stay.
Family- and pet-friendly home rentals

Back Home - Apartment in Pienza
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!

Holiday in the Chianti Senese
We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.

Casa Clara Cortona Cin IT051017c28a6h9glv
Clara was a wonderful host and very polite. He waited for us to give us the keys and explain everything in detail inside the apartment. The apartment was beautiful and made us feel at home as it had everything needed. He even left us two large bottles of water on the fridge. Cafe y te yemos as if you were coming back your house. Highly recommended.!!!!We'll be back!!!!

Poggio Bestiale Vacation Home
The accommodation is as described and perfect for a relaxing vacation. Optimal location for reaching Argentario and at the same time enjoying silence and a fantastic view on the way back. The apartment is very well maintained and clean, Denise is a superlative host, we were very, very satisfied.

loft in the heart of Tuscan Chianti
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.

Romantic cosy flat - Toscana Italy
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

La Manonera Farmhouse "La Casa Rosa for families"
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:-)

Pink like the sunset sky
Very lovely place, clean and beautiful. Lucia is very friendly and responsive for everything. Thank you
Family-friendly home rentals with a pool

Medieval Cottage near Cortona
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!!

Enchanting Rose Garden Pool Villa
We booked Villa Montechiarone as part of our wedding at Montechiaro Organic Winery to house a group of 7 guests. The property sits around 500m from the winery itself, with views out over the Tuscan countryside, it's a breathtaking location and the villa itself is an incredible space. There are 2 huge indoor living areas, a well equipped kitchen, 4 spacious bedrooms and an outdoor covered terrace, as well as the garden and pool area. There is real character in the property in the way it is decorated as well as the imposing facade of the building itself. The pool area is spacious and well placed to take in the most of the view, and there is a car port with parking for at least 4 cars covered, with plenty more room if required beyond. Overall perfect for housing our guests who had a great experience and were very thankful for the help whilst checking out also!

Private Villa with swimming pool in Tuscany
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!

Casa di Lyndall - Entire house with exclusive pool
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!

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza
Sabrina and her family were very accommodating and amazing host! The whole stay was superb In every way and my whole family as well as myself noted it couldn’t have been a better experience. From the amazing home cooked breakfast, to the cleanliness of the house, and the well thought out and led cooking class/dinner we enjoyed every aspect. Sabrina was very welcoming and made you feel like family :) I would highly recommend to anyone looking for a peaceful farm style stay that wants to experience Tuscany.

Beautifully restored villa with private pool
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

House with private pool, air conditioning
We were a family of 5 with two 20 year old boys and an eleven year old girl. We loved the homely feel of the farmhouse. It had everything we needed for our 10 day break. The gardens and pool were amazing and we loved the two different sitting areas. If you are looking for somewhere to get away from it all then this is a great option. There are a few nice restaurants within a ten minute drive and the towns of Orvieto and Bolcina were great to visit. We also used the train service to go to Rome which was very easy. You definitely need a car when staying here. Andrea was friendly, very helpful and on hand if you needed anything. Would definitely recommend this fantastic holiday home.

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2
Paula has not only created a beautiful sanctuary that perfectly reflects Tuscan culture, but offers wine tasting and a vineyard tour on her property. The location of this gem of a place is centrally located in the Chianti region , making it a perfect home base for day trips to Assisi, Firenze and nearby small villages that offer great restaurants and quaint shops. The region is cycling friendly, as well as offering places for day hikes. Staying here for five days was one of highlights of our Italian adventure.....and we highly recommend experiencing the perfect place to stay in Tuscany and the warmth and friendliness that Paula, Ferderico and her staff offer!!
Quick stats about vacation rentals that are family-friendly in Montalcino
Total rentals
500 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
12K reviews
Pet-friendly rentals
300 properties allow pets
Rentals with a pool
270 properties have a pool
Rentals with dedicated workspaces
200 properties have a dedicated workspace
Destinations to explore
- Florence Vacation rentals
- Elba Vacation rentals
- Pisa Vacation rentals
- Rome Vacation rentals
- Bologna Vacation rentals
- Cinque Terre Vacation rentals
- Portofino Vacation rentals
- Riviera di Levante Vacation rentals
- Francavilla al Mare Vacation rentals
- Genoa Vacation rentals
- Italian Riviera Vacation rentals
- Verona Vacation rentals
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Rentals with an EV charger Montalcino
- Cottage rentals Montalcino
- Rentals with a fireplace Montalcino
- Vacation home rentals Montalcino
- Smoking-friendly rentals Montalcino
- Apartment rentals Montalcino
- Rentals with breakfast Montalcino
- Condo rentals Montalcino
- Bed and breakfasts Montalcino
- Rentals with a firepit Montalcino
- Rentals with pools Montalcino
- Farmstay rentals Montalcino
- Rentals with a sauna Montalcino
- Luxury rentals Montalcino
- Kid-friendly rentals Montalcino
- Fitness-friendly rentals Montalcino
- Rentals with a washer and dryer Montalcino
- Rentals with a patio Montalcino
- Rentals with outdoor seating Montalcino
- Rentals with a hot tub Montalcino
- House rentals Montalcino
- Family-friendly rentals Province of Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- CavallinoMatto
- Marina di Grosseto beach
- Avignonesi Winery Fattoria Le Capezzine
- Santa Maria della Scala
- Cavallino Matto
- Kite Beach Fiumara
- Casa Barthel
- Tenuta Le Velette
- Podere La Marronaia, Sosta alle Colonne
- Cala Violina
- Cantina Stefanoni
- Madonna del Latte
- Cantina de' Ricci
- Cala Di Forno
- Riva del Marchese
- Ugolino Golf Club
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Cantina Contucci
- Pubblico Palace
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Castiglion del Bosco Winery
- Podere Il Cocco
- Golf Club Toscana
- Casa Del Cioccolato Perugina
- Things to do Montalcino
- Nature and outdoors Montalcino
- Food and drink Montalcino
- Things to do Province of Siena
- Sightseeing Province of Siena
- Tours Province of Siena
- Sports activities Province of Siena
- Art and culture Province of Siena
- Food and drink Province of Siena
- Nature and outdoors Province of Siena
- Things to do Tuscany
- Wellness Tuscany
- Art and culture Tuscany
- Sightseeing Tuscany
- Sports activities Tuscany
- Food and drink Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Nature and outdoors Tuscany
- Things to do Italy
- Sports activities Italy
- Entertainment Italy
- Sightseeing Italy
- Art and culture Italy
- Tours Italy
- Food and drink Italy
- Wellness Italy
- Nature and outdoors Italy