Kid-friendly holiday rentals in Montalcino

Breathtaking location with views that are exactly what you want in the Chianti region. It was a beautiful place and was very nicely setup. Extremely responsive and helpful host. He provided recommendations and was quick to respond to questions. The house is centered nicely within the region and allows access to many different villages, wineries, and restaurants. An amazing experience and I highly recommend!

We highly recommend staying here. The house is fantastic and the apartment in it allows you to feel the atmosphere of the town. We spent very pleasant moments in it. The terrace is definitely an asset of this place. Simona hosted us wonderfully, she was very nice and very helpful. The contact was always very smooth and pleasant, we felt very cared for. Thank you.

Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!

Great flat to explore Cortona! Excellent location and had everything you need

Staying at Torre “La Lambarda” Suite was an absolute dream come true. Nestled atop the enchanting village of Monticchiello, this historic tower offers breathtaking panoramic views of the Val d'Orcia that are simply unforgettable. The suite itself is a perfect blend of medieval charm and modern comfort, with every detail thoughtfully curated to enhance the guest experience. Although I didn’t meet Deb personally, her team provided outstanding hospitality throughout our stay. Every member of the staff—both at the property and at the wonderful restaurant—was warm, attentive, and genuinely kind. Their care and professionalism made us feel incredibly welcome and well looked after. Dining at Deb's Lounge was a true highlight. The food was exceptional, the ambiance cozy and intimate, and the staff went above and beyond to make every meal special. This stay was more than just a vacation; it was a magical journey into the heart of Tuscany. I wholeheartedly recommend a stay in the Tower.

We loved our time at Luca's place. We visited Tuscany with our college aged kids. Luca's house was comfortable and welcoming. We went out for a few meals, but also enjoyed preparing foods in the wonderful kitchen. We ate dinners together and played board games on the spacious kitchen table. It was homey. We called it "cucina magica" because all of the foods we cooked came out so perfectly. This is a wonderful home in a lovely setting with hiking trails from the backyard. We spent several mornings at the nearby hot springs. What a treat! Luca was communicative and helpful with all of our questions.

absolutely one of the best AirBNB experiences we have ever had! There is no better location if you are visiting Siena, especially if you would rather take the escalator up the mountain. The entrance is right across the street. Our host had thought of everything. From washing detergent to a bottle of wine. Take not though, in Siena it is sometimes difficult to get a taxi early in the morning unless you book it well in advance. Our host went out of his way to make sure we arrived at the train station on time! But just remember, book your departure taxi early! And oh yeah, the secret garden was awesome. A great place to kick back and enjoy the mountain air with a cool beverage;) 5 star plus plus!!

We loved staying in Montalcino at Lisa's place. Lisa was a fantastic host and responded quickly. She gave us her picks for restaurants, wine tastings, etc, which were excellent choices. The Airbnb was ideally situated right off the main square. It has a yard, which we enjoyed, and a very functional kitchen with everything we needed. The king-size bed was very comfortable and had high-quality linens. This is a hilltop city, so keep this in mind for anyone unable to walk up steeper inclines throughout the city. We enjoyed the exercise and the stunning views. We stayed for a week and I could have easily stayed longer as we got to know the restaurants, stores and the area. Montalcino is a charming place to spend your time. It was a good location from which to take day trips. There is so much to do in the general area. We highly recommend you stay here; it was the highlight of our trip, and we felt like we were in good hands. Thank you, Lisa!

Paradise on earth - for both nature lovers and wine lovers alike! The natural beauty of Alexandra's airbnb cannot be described by words... from the views and organic landscaping, to the sunrise, sunset, and peaceful atmosphere, this place will take your breath away. The proximity to Montalcino and the surrounding wineries is fantastic! We were able to walk to town and were only a short drive away from multiple wineries. We chose to take advantage of the outdoor grille and kitchen to cook most of our meals from home. Thank you Alex for the recommendation to head to Buonconvento (the town near montalcino - a 10minute drive) for the large grocery store we utilized to stock the kitchen! Both Alex and Michelangelo were helpful hosts when needed, but gracious enough to allow full privacy - even though they live in the attached larger home, you would never know. The 4 days we stayed here were 100% the highlight of our trip! I am grateful they share this space with the world!! ⭐️⭐️⭐️⭐️

A Magical Stay in the Heart of Tuscany Our recent stay at this agriturismo in Asciano was nothing short of spectacular. Despite the weather not being on our side, the breathtaking views of the Tuscan countryside more than compensated. The illuminated pool at night added a romantic and unique touch to our stay, creating an enchanting atmosphere that we'll always remember. We stayed in a well-appointed apartment featuring a spacious master bedroom, a comfortable living and dining area, a fully equipped kitchen with all necessary utensils and cutlery, and a newly renovated bathroom. The accommodations were incredibly comfortable, making it an ideal choice for a long and pleasant stay. The combination of stunning landscapes, cozy interiors, and thoughtful amenities made our experience truly unforgettable. We highly recommend this agriturismo to anyone seeking a serene and romantic getaway in Tuscany.

My husband and toddler and I had a phenomenal stay at Elvira's place. The location is beautiful and quiet. It was our favorite place we stayed in Italy. Highlights: We rented bicycles and went on the most beautiful bike ride I've ever been on. There was a 3 day festival in one of the towns a few minutes away which we attended and we loved the sense of community there. Elvira was the most gracious host, very responsive, friendly, and generous.

We are so glad for the six days we were able to spend in Tuscany at Marta’s home! The setting is so peaceful – nothing but rolling hills and fields around, with the city of Siena in the distance. Sienna was only 17 minutes away by car, so we went for restaurants, market day, and sightseeing. We were also able to explore multiple other towns in Tuscany. This was a great central location for us. When we wanted to stay at the apartment, we enjoyed nice privacy, our own picnic table and gazebo, and soaked in the hot tub one evening. Marta’s wine (the first bottle is free) was fantastic. If we come to Tuscany again, we will certainly try to stay here!

The house is very brautiful, the gardens are amazing. We only stayed for two nights, but we had such a beautiful time there. There are a few garden spots to seat, realax, drink coffee or have breakfast. So beautiful. We had a realy nice stay. The owner was very kind, even offered us a coffe and let us stay an hour longer so we didn't need to hurry to check out in the morning. There are a lot of very beautiful spots near Torrinieri, so this was a perfect location for exploring Tuscany by car.

Wow!!! What can I say about this most magical place that hasn’t already been said? 10/10 recommend Simone’s place. We will be talking about this stay for years to come. The property, the communication, the hotel amenities (restaurant Zita was wonderful but the spa massage experience was out of this world), the scenery. Just wow! Book this place while you can. We feel so lucky to have been able to stay here on our 2 week Tuscany adventure. Grazie!

This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.

We had a wonderful stay at Luca’s and the view cannot be beat! Luca went above expectations by meeting us at checkin to show us where to park and taking our luggage to and from the unit. Hope to stay here again one day!

We stayed for 5 night and enjoyed this large, well appointed two story apartment. The place was warm and inviting and was an authentic home to be a unique setting. My family enjoyed the surroundings and there was plenty of restaurants to close from. Be prepared to tackle the 52 steps to the apartment door which my 90 year old mother managed twice a day. Keeps you healthy.

Very pleasant stay in the historic center of Chiusdino, a great place to visit the beautiful area. Apartment clean and equipped with everything you need. Franca is very helpful and proactive. Recommended.

Leonardo was incredible helpful and an absolute delight. You can tell he is house proud, the place was peaceful and beautiful. I would go back.

Marco’s place is away from the hustle and bustle of Siena very quietly comfortable and super clean. The view from the balcony alone is worth the night rate. Close to all the lovely sights in Val D’Orcia. In a very quaint town with locals who actually live here. Marco is very responsive and clearly explained everything to us. Must try the pizza at Pizza I’ll Vecchio…a hidden gem in Tuscany

We had the best time!! The cutest little apartment with a nice little balcony. Loved the exposed beams and the kitchen. It was very walkable to great restaurants and scenic views, also far enough away were you are not worried about noise at night. Host was super responsive and had excellent recommendations on where to eat and what to do!

It’s easy to understand why this apartment is so well rated! From the location, the views, the well appointed kitchen, the mini split, the fun decor and engaging book collection, the cleanliness, etc. Simona was an ideal host: communicative and helpful. Visiting charming Ovieto was made even more so with our stay in Milva’s Nest. Grazie mille, Simona!

Very comfortable accommodations and gorgeous property and views

I can’t say grazie enough to Gessica and Bernardino! Such nice people. The apartment is one of the best Airbnb’s I’ve stayed in. Pictures don’t do it justice. It has everything you could ever need. The view from the balcony made it hard to leave. Hopefully we will be back! Grazie Mille!!