
Family-friendly vacation rentals in Massa Marittima
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Top-rated family-friendly rentals in Massa Marittima
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Popular amenities for Massa Marittima family-friendly rentals
Family-friendly home rentals with a hot tub

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!

Relax in the countryside near the sea( Lavanda )
Isabella is a nice and helpful person, she welcomed us to her beautiful villa and immediately put us at ease. Great tips on places to visit and where to eat. The accommodation has all the comforts, beautiful salt pool, unfortunately not available since the season has not yet started. I'll definitely be back, thanks for everything Isabella!

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
We spent a week at Il Vichiaccio and I already miss the house. The house was perfect for a family of 5 adults. We felt immediately at home, had all what we needed. The location and views are awsom, even more beautiful than in the pictures. Plenty of great wineries and restaurants in the ares. Beatrice is a great host, answered every question we had, gave us recommendations and even helped us when our daughter didn't feel well. We strongly recommend!

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!

Romantic stay where Tuscany meets the sky!
This place is definetly worth to visit. the area is full of nice walks in the nature. Monica's place is fantastic in every aspect and she is a lovely and caring host always availble for guests needs. can't wait to visit again!
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!

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.

Small house
We found the apartment very clean and as described, and the hosts were very friendly. They gave us tips for excursions upon arrival. Anna Maria and her husband have created a little paradise here. If you are looking for peace, you will find it in this beautiful environment. The terrace is not only perfect for sunsets, but also for the view of the starry sky! The space was sufficient for us with two children, as we were mostly outside anyway. We can recommend the small shop in neighboring Colle d'Orano. We enjoyed the week in Patresi very much!

Casa Clara Cortona Cin IT051017c28a6h9glv
Small but very well equipped apartment, centrally located. Great solution for those who want to stay in an extraordinary village like Cortona.

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!

Paluffo Tower House
Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.

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

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!

Poggio Martino | Childfriendly Agriturismo
We had a wonderful stay at Poggio Martino!! We did not struggle to find it on the map. Francesca was flexible with us and left instructions and a key so we could check in late. In the morning, she made me an espresso to drink while I completed the check in process! She was always kind and responsive. We loved the accommodation and could not get over how beautiful it was. We appreciated the high chair and portacot with warm baby duvet put in our room for our daughter. Our bed was so comfortable and we were pleased we could cook something in the kitchen. Having tupperware in the kitchen was very useful and appreciated, as well as all the necessities like seasoning and oil on the kitchen bench. Feeling lucky to have gotten the only two available nights here in quite a few weeks of it being booked out!

Restored Farmhouse & Cottage with AC, Pool & WIFI
For our family vacation, three couples and a 1-year old, the place was perfect. The ability to spend the heat of the day in the huge pool or inside the refreshing lodging made the stay excellent. The place is close to groceries, pharmaceuticals, restaurants, local sites, cities, etc. Ken was always responsive to whatever issue we brought up and his quick replies were greatly appreciated.

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!

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

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!

Agriturismo Palazzi del Papa 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.

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.
Quick stats about vacation rentals that are family-friendly in Massa Marittima
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
680 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Giglio Island
- Feniglia
- Mount Amiata
- Val di Chiana
- Gulf of Baratti
- Spiaggia Libera
- CavallinoMatto
- Spiaggia Verruca
- Spiaggia Zuccale
- Marina di Grosseto beach
- Spiaggia Di Sansone
- Spiaggia di Marina Di Campo
- Kite Beach Fiumara
- Spiaggia di Patresi
- Cavallino Matto
- Spiaggia di Capo Bianco
- Santa Maria della Scala
- Casa Barthel
- Cala Di Forno
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Di Sottobomba
- Cala del Leone
- Spiaggia Marina di Cecina