Family-friendly vacation rentals in Massa Marittima

Everything was great about the stay! We were really starving the day of ur arrival and Francesca was able to bring us some food for her that was all needed to kick start our day!

If I could move in here permanently, I would. What a gorgeous stay with responsive and respectful hosts. Everything was as described, the hot tub was glorious, and we loved looking through the binder of photos of painstaking restoration over the years.

I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!

Simply unbelievable – a secluded haven with everything you'd want from a holiday home in the Italian countryside. We spent 6 days with our two young kids at Monica's place, and had one of the best holidays ever. The house is beautiful, well-equipped and charming, and the views are out of this world. Sunset out of the bedroom window will stay with me forever! Then there's the gardens - lots of room for kids to run around in complete safety, with a large infinity pool (cold in May, but still enjoyed every day by us and the kids… the view was so beautiful I proposed to my fiancee there 🥳), and also a playground and outdoor bowls lane. There's an excellent restaurant within 5 minutes walk, but Sillico is a quiet, beautiful medieval hamlet and not much more – be aware that to get anywhere you'll need to drive 12 minutes down quite a narrow twisty road. It didn't bother me, but just something to be aware of for less confident drivers. Overall: one of the best places I've ever stayed!

Without any doubt the most special Airbnb I have ever stayed at. My multigenerational family came here after a rough year and it was a tonic. It is not often in one’s life you have the opportunity to sit and look out at views like that hour after hour - the towns across the bay, the boats coming and going (including a submarine), the lights coming on in the evening… It is so much better than any words or photos could express. The swims were also outstanding. Brian was delightful and so helpful with recommendations. We will be back

We can absolutely recommend it! Everything is as described in the text and seen in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information about the arrival and many great local tips, always with the corresponding links. For example, our arrival was delayed due to traffic to about 10:15 pm. Was no problem, we were in contact and when we arrived, Andrea personally welcomed us. And if we had a question during our stay, an answer always came very quickly. (Where to park in Siena, how to get to Florence, ...)

Fulvia’s apartment is a true Tuscan gem—beautifully decorated with charm and character, and equipped with everything you need. The property offers stunning views and a peaceful sense of seclusion, and it’s even more beautiful than in the photos. Fulvia is right nearby and always available if you need anything. She and her husband are both warm, thoughtful, and made us feel genuinely welcome. Fulvia even arranged dinner at a local restaurant, which turned out to be one of the best meals of our trip. This is a special place and our only regret is not staying longer.

A little paradise in Tuscany with the most breathtaking view. We spend alot of the days at the house, swimming in the pool, cooking and generally feeling at home! They surprised us with fresh cherries 🍒 a few times and were happy to explain the beautiful routes you can walk around. We will def be back! ❤️

Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

Giuliani is a wonderful host who made us feel as if this slice of paradise was our home, too. The location, the meticulously restored home, the views all make for the ultimate Tuscan experience. But Giuliani and her husband bring it all together with their warmth and attentiveness. It was a tough place to say goodbye to — for now. If you are looking for a Tuscan experience, this is it. And remember to ask for the hosts’ home-cooked meal. It is a culinary experience in the very best sense.

We immediately fell in love with this property. Everything here makes up the image that can be made of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!

My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!

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!

Francesco was the perfect host very communicative and responsive when needed - the unit was spotless and nice decor - loved being in the little town walking to the 3 lively restaurants, grocery and coffee shop not to mention the fabulous vineyards that surrounded the flat - we did some wonderful walks and did side trips to cute little towns - Would recommend highly

We come from Hong Kong, and a building like this is not often seen there. We are very happy to have had the chance to stay at the house. Some of the details in the house really impressed us, especially the antique furniture! Pietro is a great host—very friendly and responsive. I had some pleasant conversations with him. Thanks again!

we stayed 3 nights at Gaia's and everything was great! The roof terrace is really a highlight! Huge for private use and with a mega view of the sea, a small harbor and the island of Elba. Gaia was always available through the app and quickly helped when there were questions. Only the doors were a little loud to open and close. But Gaia has already hired a carpenter and I think the problem will be fixed soon.

We loved our time here! It was a beautiful property exactly as described. Alessandra has great recommendations and lovely wine. We will be back!

We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!

Beautiful rustic stay in the heart of Tuscany. Manuela was very friendly and helpful. The farm at night with the fireflies lighting up the bushes and nightingale singing in the trees was absolutely enchanting.

Fabio and Sarah's farm is a true oasis of peace and tranquility! We were warmly welcomed and immediately felt at home! It was an extremely pleasant stay in the spirit of nature and the beautiful surrounding landscapes. The pool, overlooking the valley, is really beautiful! The accommodation provided is well maintained and tastefully furnished! Fabio was very helpful and kind: he was a great help in solving a problem we had just arrived! We will definitely return to this paradise... a wonderful place where you slow down and rediscover the beauty of nature 💚 Thanks Fabio and Sarah!

The perfect place to explore Chianti each day. We stayed 5 nights and it was just perfect. Great amenities, beautiful pool, bbqs and lovely areas to sit and enjoy the views and the sunset. Always fabulous to come home to. Our upstairs apartment was spacious, comfortable and all we required with a lovely view. We had great recommendations from Silvia which we followed up on. Great to have restaurants nearby. Reasonable- highly recommend.

We had the most magical stay at this Tuscany farm! The property is absolutely stunning — nestled among rolling vineyards and olive groves, with postcard-perfect views in every direction. Our apartment was spacious, charming, and had everything we needed for a comfortable stay. The hosts were incredibly kind and welcoming, sharing local recommendations. Our kids loved meeting the animals, exploring the grounds, and especially swimming in the beautiful pool overlooking the hills — it was a total dream! Evenings on the terrace with a glass of wine and the Tuscan sunset were unforgettable. This was a once-in-a-lifetime experience for our family, and we can't wait to return. Highly recommend to anyone looking for a peaceful, authentic Tuscan escape! 🌿🍷☀️

While Paolo was away, our check-in and communication with Bruno went very smoothly. The property is absolutely stunning. The view of Sam Gimignano as you swim in the pool was something out of a movie scene. The property has surrounding olive trees and vineyards seen right from the window of the airbnb. This particular room is in a tucked away corner of the property and feels very private. Bed was comfy. Washing machine and drying racks, as well as a grill were plusses. Many agriturismos offer a dinner for an added fee, and we were a little disappointed that the dinner (in the past offered by Paolo’s neighbors) was closed during our stay. However, in fending for ourselves, we did appreciate the mini fridge and microwave, and loved eating our dinner right on the private table outside the room door. Also, you do have to clean out your trash at the end of the stay. Price felt right. Overall, would happily stay again and will be forever dreaming of the view.

This was such an amazing stay! Very quiet, peaceful, and relaxing stay far away from the major cities. Beautiful views from everywhere! Would recommend doing their wine tour on site. It was fun, informative, and delicious! You definitely will need a car to get to this place in addition to restaurants and grocery stores. Would highly recommend this place!