
Family-friendly vacation rentals in Montaione
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Top-rated family-friendly rentals in Montaione
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Popular amenities for Montaione 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 :)

Holiday House "The Seasons of Bacchus"
The house is so nice, clean and cozy. Daniele gives us many helpful tips and place to go, very nice and proactive host.We enjoy our stay very much thanks to Daniele. The place is peaceful and easy to go anywhere, Pisa, Lucca, Florence and Cinque terra. Such a lovely house , highly recommend for family trip👍🏼

CASA AL BOSCO 1
We had a very pleasant time here. Carlotta was very friendly from the start, and even recommended local grocery stores. This place is a hidden gem! You are surrounded by beautiful trees & nature, but close enough to the town where you can easily catch the train to Florence. We absolutely loved it!

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!

M&G Apartment your home away from home
Beautiful and cosy place located at a convenient location. We enjoyed our stay. Highly recommended!

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!

Romantic stay at a bio-agritourism in Florence
This was one of our favorite Airbnb stays and experiences. The farm is beautiful, well-located, and sustainable. It offers tranquility and genuine hospitality. We highly recommend the cooking class we took with Francesa. She not only taught us how to cook amazing pasta, but she also taught us so much about ingredients and served us incredible food sourced locally. It was an unforgettable experience. Francesca and her family were so welcoming and made us feel at home. Their farm work is inspiring, and we appreciate their work and genuineness. We will definitely return soon!
Family- and pet-friendly home rentals

La Maison di Monica & Simona
Really enjoyed the stay: the place is spacious and cozy (even more beautiful than in the pictures :)), there was everything you need: bed linen, towels, everything equipped with kitchen. The hosts are friendly and although they don't speak much English, but they explain everything:)... The town is charming too - full of historical buzz. There is a small thermal spring quite close (from the property maybe 5 min walk) - quite hot so only one of us bathed, but our feet were all soaked;)... We had a wine at the townhome's bar - it was very nice to interact with the locals. Literally, the warmest feedback - thank you for everything!

Within walking distance of the center and away from the chaos
Stefania was very welcoming and easy to communicate with. Her home is in a nice area away from the crowds. We chose to walk into the centre but there is a bus station close by.

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.

Antico Borgo Ripostena – n. 5 Garage
Marina's place is one of the most beautiful places I've ever seen. The attention to details, the amenities and her communication made our stay very relaxing and enjoyable. Thanks Martina for a great stay in Tuscany.

APARTMENTS 3 people + 4 people
Claudia is a great hostess, always very helpful and super nice. We felt very comfortable. The apartments have everything you need, the pool is great - very clean and with a wonderful view. The location is also great - in about 15 minutes you are in the Volterra and up to San Gimignano you only need half an hour. We will be happy to come back and thank you for the delicious oil and the nice holiday!

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.

House in Tuscany with pool
We spent a wonderful week in Cristina's house in Fabbiano and really enjoyed our break from everyday life there. The house is beautifully integrated into the small, quiet, very romantic place. You enjoy a wonderful view of the valley and the mountains from the garden and can also take a beautiful hike from the house. Cristina's welcome was very warm and made us feel really welcome in her house. We could always ask them if we needed advice. The garden is fantastic. Unfortunately, it was already too cold for the pool. For this, we enjoyed the fireplace very much. Despite the mixed weather, we did a lot because the house is centrally located between the sea, the mountains and some very beautiful cities (e.g. Viareggio, Lucca, Pisa, Bargo). Since the garden is completely fenced, our dog was also able to move freely the whole time. For small families who love tranquility and seclusion, the house is ideal

House at Gianni - Leccio
Our stay on the farm enchanted us! The environment is amazing. The apartment was clean and bigger than the pictures. We were able to have farm products (meat, pasta, eggs, beers) and enjoy the facilities (ping pong, freesbee, badminton) The kids loved being able to see the pigs and donkeys up close. A fireplace to top it all off, a stay in the heart of nature that is truly exotic and relaxing. Super responsive, friendly and attentive host. 👍👍
Family-friendly home rentals with a pool

Tuscan Villa with Privacy,Pool,near towncentre
Paradise environment, in a spectacular setting, very close to the center. House full of all comforts, elegant, perfect for a total relaxing stay. Antonio is always ready to meet your every request, kind, friendly and hospitable. Definitely back!!

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!

Tuscan Villa
Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.

Casa del Sole
We had a great time at Carlo and Elena's. The fenced garden and swimming pool were a real plus. Not to mention all the little touches Carlo was able to have for us, and even a gift for our little puppy. The place is peaceful surrounded by mountains with beautiful views. We would recommend this house and its host because everything was perfect!

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!

La Felce Country House
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!

Casa Colle
We had a very relaxing few days staying with Lucy and her family, and their dog Amber. They were really friendly and welcoming, and always ready to answer any queries we had. The pool area was lovely, and extremely peaceful. The accommodation was spacious, very clean and comfortable. The village is small with a butchers and bakers, a couple of restaurants and a bar. We did a lovely circular walk from the property through the woods to the nearby hill top village, Castel Vecchio. There’s nothing in the village but it’s very pretty and the views are great. You need a car to get to the supermarket and Lucca is a very easy 20 minute drive away. We had a super time and thank you Lucy for your generous hospitality.

Villanuova Power 2
Great location - close if you are flying into/from the Florence airport - extremely close to to Villa Antinori - Dario Ceccini in Panzano - San Gimignano - Siena, etc. Pictures are representative of the apartment - grounds exceed the pictures. Grounds are very well maintained. The pool is exceptional. Great cats and dogs to welcome you throughout the day. Kitchen is very workable, knives are sharp, gas stove and kitchen utensils are stocked and ready for your carbonara or amatriciana. Plenty of staff is located on premises but are not at all intrusive. 11 out of 10. Will return.
Quick stats about vacation rentals that are family-friendly in Montaione
Total rentals
20 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
140 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Santa Maria Novella
- Duomo di Firenze
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- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
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