
Family-friendly vacation rentals in Grosseto
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Grosseto
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 Grosseto family-friendly rentals
Family-friendly home rentals with a hot tub

Deal 2019 Tuscany Villa le Capanne with pool
Ginaâs place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.

Tuscan Villa:Pool,Hot Tub,A/C,wi-fi,7bd near Siena
Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place

Relax in the countryside near the sea( Lavanda )
We had a great time with the family in this peaceful little corner in the middle of nature! Isabella is a great host! thanks đ We recommend it!!

Villa in Montepulciano with a Pool
Alex, u show such hospitality to our family!! We love how well u maintained the place. The view from our hotel brings smile to my face every morning! Itâs spectacular. Iâll definitely come back! Hope the price is reasonable the next time đĽ°

Charming estate with views
The best BandB we ever stayed. I am a very OCD person and I was very impressed how spotless and polish the place was. Everything was carefully thought out. Everything you need is in the place. Bernadino and His wife Luciana were amazing. Providing us with homemade Italian food and taxi services. They were so friendly that I am happy coming back with my kids. The view was breathtaking. Absolutely loved everything.

Villa di Geggiano â Guesthouse
Vila Di Geggiano was everything we were expecting it to be and more. We simply loved the place, quiet and very comfortable, set in the middle of a beautiful Toscana. The guest apartment is located by the side of the Main House, a historical summer palace with a deep history behind it. Andrea, our host, gave us a personal tour of the main house, filled with great stories about his ancestors. The house has been in Andrea´s family since the 1500s! If you are looking to spend some quiet days enjoying the great food and wine of Toscana in a relaxed, unique and comfortable space, Vila di Geggiano is a great destination for you.

Your Private Tuscan Retreat
Our stay at Riccardo & Kate's property was fantastic, the property is as described, the views were awesome. Riccardo was more than happy to help us with local recommendations & bookings when we needed help as we speak next to no Italian. The local town of Castell'Azzara is a beautiful place & the local people were very helpful at the Coop, bakery & restaurants.

Tuscany Seen in a Fabulouse House
Very nice and clean appartment in a very quiet area. Only Met Gaston shortly since we were out all day visiting Tuscany with friends, But he was very Friendly. Will definitely come back
Family- and pet-friendly home rentals

La Maison di Monica & Simona
Monica is very welcoming. The value for money is very good. Be careful if you have small children because there are slightly steep stairs to access the accommodation.

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 designed a little paradise here. If you are looking for peace, you will also 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 usually outside anyway. We can recommend the small shop in neighboring Colle d'Orano. We really enjoyed the week in Patresi!

Ground floor studio apartment in Farmhouse - pool
Everything is beautiful! Clean and well equipped room, the kitchen with a view of the garden and the Maremma fields. We fell in love with it, highly recommended!

Casa Clara Cortona Cin IT051017c28a6h9glv
We had an incredible stay at Clara's property in Cortona! The highlight of our trip was definitely the visit to the farm, which was not only fun but also deeply meaningful. We loved learning about the local way of life. Our host, Clara, was warm, welcoming, and extremely helpful throughout our stay. They went above and beyond to ensure we felt at home and had everything we needed. The property itself was clean, comfortable and well-located. We would highly recommend to anyone looking for an authentic and unforgettable experience in Cortona. Grazie mille, Clara for sharing your little slice of heaven with us!

Poggio Bestiale Vacation Home
The accommodation is as described and perfect for a relaxing holiday. Great location to reach the Argentario and at the same time enjoy the return of a silence and a fantastic view. The apartment is very nice and clean, Denise is a superlative host, we were very very satisfied.

APARTMENTS 3 people + 4 people
Claudia is a great host, 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 it only takes half an hour to get to San Gimignano. We will be happy to come back and thank you for the delicious oil and the beautiful vacation!

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
We had a wonderful time at Luciaâs place . The house is charming and very clean . It is in the heart of beautiful Tuscany and you have exceptional view from every window . Checkin was easy and host is very kind and responsive . Highly recommended for a wonderful experience of Tuscany .
Family-friendly home rentals with a pool

Medieval Cottage near Cortona
Words canât 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!

Idyllic with shared pool in the heart of Chianti
Heidi's apartment is situated in a larger complex on the outskirts of the village, just a short walk from the town center where you can find a church, a mini supermarket, bars, and a popular restaurant that is always fully booked. The village is ideally located in the heart of Chianti, making it a perfect starting point for exploring the region. You can drive along one of the scenic, winding roads to a wine tasting event, enjoy a bike ride through the picturesque countryside, or visit nearby cities like Siena or Florence (Firenze). One of the highlights of the apartment is the spacious swimming pool (1.35 m deep), which is perfect for cooling off during the hot summer days, especially if you have kids. The apartment itself is well-equipped, ensuring a comfortable stay. Communication with Heidi is easy and friendly. She provides detailed information on the check-in and check-out procedures, as well as instructions for using various amenities in the complex. We enjoyed our 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!

Lovely villa heated outdoor pool & tennis court
The villa exceeded our expectations. It was exceptionally clean and well cared for. Excellent amenities. Beautiful surroundings with olive and lemon trees. Cute little village nearby with an excellent restaurant. The host was very responsive. We had a bit of trouble finding the place but that might be more us than the directions. You definitely need a rental car Thank you for an amazing stay

Agriturismo Palazzi del Papa Val d 'Orcia Pienza
Nice agriturismo, very chill place and beautiful surroundings

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

Restored Ancient Farmhouse
The house was large and roomy and each room had a private bath with a good shower. The kitchen was well equipped. The hostess was extraordinarily generous with the little things she made available to us. We might have wanted to grill for a dinner but the outdoor grill was rather greasy and not appealing to use. The one drawback ( that was not her fault) was the horrible condition of the road leading to the house. All in all, a great stay.
Quick stats about vacation rentals that are family-friendly in Grosseto
Total rentals
40 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
480 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
- Florence Vacation rentals
- Pisa Vacation rentals
- Rome Vacation rentals
- Bologna Vacation rentals
- Cinque Terre Vacation rentals
- Portofino Vacation rentals
- Genoa Vacation rentals
- Italian Riviera Vacation rentals
- Francavilla al Mare Vacation rentals
- Verona Vacation rentals
- Venice Vacation rentals
- Menton Vacation rentals
- Pet-friendly rentals Grosseto
- Smoking-friendly rentals Grosseto
- Rentals with outdoor seating Grosseto
- Villa rentals Grosseto
- Bungalow rentals Grosseto
- Rentals with a patio Grosseto
- Beachfront rentals Grosseto
- Rentals with a washer and dryer Grosseto
- Condo rentals Grosseto
- Apartment rentals Grosseto
- House rentals Grosseto
- Family-friendly rentals Province of Grosseto
- 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
- Spiaggia Zuccale
- Spiaggia di Capo Bianco
- Arcipelago Toscano national park
- Spiaggia Di Sansone
- Spiaggia di Marina Di Campo
- Spiaggia di Seccheto
- Spiaggia di Marciana Marina
- Spiaggia Di Sottobomba
- La Sorgente beach
- Spiaggia di Seccione - Portoferraio
- Spiaggia di Bagnaia
- Fosso alle Canne
- Spiaggia della Padulella
- Spiaggia di Ortano
- Spiaggia di Acquarilli
- Spiaggia di Cavo
- Spiaggia Di Barbarossa
- Calamoresca
- Spiaggia Marina di Cecina
- Cantina de' Ricci
- Cantina Winery
- Cantina Contucci
- Madonna del Latte
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes