
Kid-friendly holiday rentals in Province of Grosseto
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Province of Grosseto
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Province of Grosseto family-friendly rentals
Kid-friendly house rentals

La Casa del Valle
I immediately fell under the spell of the charming flowery facade decorated with a whole bunch of little curiosities☺️. I also loved the romantic room with the wrought iron bed and the classic-style wardrobe. Lovely! And Déborah is very available. Thanks to her.

La Casetta di Alice - with panoramic terrace -
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.

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
We felt like kings of the castle in Stefano and Sylvias’s place. Top of a hill with expansive views and always such a beautiful breeze. San Quirico was lovely as was Bagno Vignoni at the bottom of our hill. We could see the twinkling lights of Pienza and Montepulciano both of which were an easy drive away. Generosity in the way the villa was presented and our hosts’ welcome, with many wonderful local suggestions. Would highly recommend.

"La Lambarda" tower Suite
A truly wonderful place, no other place like it. Really worth seeing but only if you are able to handle the 54 step very narrow spiral staircase. The house is on 4 levels linked by the stairs, wouldn’t be suitable for young children or the elderly. Deborah was a great host as was Paula.

Montalcino - Casa Gelsomino - garden and relaxation
Massi is a lovely guy. Really responsive and helpful. His place has a great location being in the middle of town. One minute from the town square. The house is well appointed. And comfortably housed two couples.

Country house La Meria
If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!

At the Sassone Holiday Home, Val d'Orcia, Tuscany
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.

Lovely home in villa with garden and pool
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.
Family-friendly apartment rentals

Stuart White Tea Central Panoramic & Garden
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!

I Tramonti di Eramo, Montepulciano city center.
Spectacular view. Relaxing after a long trip thru wineries. Town was very cute and comfortable

A view from the top, 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!

Casa Bonari - a paradise for the eyes
This is Tuscany at its finest! Our stay at Casa Bonari was perfect. The villa inside was spacious, beautiful, comfortable, and wonderfully Italian. It was equipped with everything we needed. The exterior grounds were gorgeous and the views from the property in every direction were breathtaking. We made dinner and ate on the patio - it looked like a picture from a magazine. The villa is within easy walking distance of the charming Monticchiello which has a few excellent restaurants. We enjoyed strolling the picturesque streets and the incredible views of the countryside from the village. Our hostess, Valentina, was very gracious and helpful. We enjoyed meeting some of the friendly family members. They were so kind and left us with happy memories. We highly recommend Casa Bonari and hope to visit again.

Panoramic penthouse in the ancient village
Loved our stay! Great set up, great location, and really responsive host. Check in was easy, we had everything we needed and the views are INCREDIBLE from the house. There’s also a nice coffee place just downstairs that opens early. Highly recommended!

HOUSE WITH SEA VIEW: KEY DELIVERY OR SELF CHECK IN
We booked Sonia's place for one night while driving from up the Coast. We now wish we had time to stay longer! It's a stunning location with incredible views from the AirBnB. The coast is only a short walk away with plenty of restaurants to choose from. Sonia sent us photos and videos before arriving which were helpful and clearly showed where to park, where to find the lockbox and keys, and how to find the apartment making the check in process super easy. A highly recommended stay.

Far Horizons:Uniquely panoramic peaceful sea views
Excellent host! And what a view!

Romantic Tower's dating 1200
What an incredible location!!! Monticchiello is the most quaint and picturesque town nestled in the heart of Tuscany. Walking up to the accommodations feels like a fairy tale - the view of the Val D’Orcia and the medieval tower you walk into, but you are then transported into the most relaxing little apartment. The amenities are wonderful - the attention to detail was not lost on us. We stayed here right after our wedding and it was exactly what we needed. Also, Deb’s Lounge was such a nice place to get breakfast (included!) and we enjoyed some fresh pici pasta for dinner our first night. Would 100% come back!!
Family-friendly apartment rentals

Le Antiche Viste - The Zen Terrace
A wonderful retreat in the heart of Pitigliano. The apartment is so beautiful and cozy and very special - you look forward to coming home every time and don't want to leave. Beatrice and her husband are super professional and at the same time very warm hosts. Really a recommendation!

Sea, Relax, Park of the Maremma Alberese, Tuscany
The accommodation was impeccable and lovingly maintained. For us, all the necessary things were available (coffee maker, pots, etc.) so that we lacked nothing in this respect. Fabio and his mother were always friendly and accommodating. During our stay, we had at least two furry pets for a while - they made our time a little sweeter. The location was perfect for us to go to the sea (tip: it is best to rent a bike here and cycle through the beautiful Maremma Park to the sea). We would be happy to come back. P.S.: be sure to pack mosquito spray ;-)

Apartamento Chiusdino - Old Town
Excellent accommodation, house as per photos and description, located in a very nice little village. Clean and tidy structure, Host always available for any information and kind.

Mascagni Farmhouse in Val d'Orcia, Pienza
The place was beautiful and so peaceful. Bianca is a great host. She was very friendly and communicated well and gave us a lot of recommendations. 5 ⭐️

[9 minutes from Montalcino] Elegant House Mafalda
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

"Landscape Notes" Suite
This was by far the most beautiful view we have ever had at an Airbnb or hotel room. The house was beautiful, but the sunrise from the balcony is something I will remember forever. Vittorio also offered recommendations, and Fulvia was flexible with our check in. The apartment is in the perfect spot to become familiar with town. We want to come back to stay here again. Thank you!

Penthouse in Porto Santo Stefano
We loved the place! Porto Santo Stefano is peaceful and charming. We took the ferry over to Giglio Island one day and rented a scooter. Really a wonderful little getaway. Thanks Antonio!

"Dimora Valinda" Montepulciano Piazza Grande +A/C
Amazing stay! Location was sensational. Everything you could ask for and more!
Destinations to explore
- Rentals with pools Province of Grosseto
- Rentals with a fireplace Province of Grosseto
- Holiday home rentals Province of Grosseto
- Rentals with breakfast Province of Grosseto
- Smoking-friendly rentals Province of Grosseto
- Rentals with beach access Province of Grosseto
- Tiny house rentals Province of Grosseto
- Rentals with a firepit Province of Grosseto
- Rentals with a sauna Province of Grosseto
- Villa rentals Province of Grosseto
- Loft rentals Province of Grosseto
- Serviced apartment rentals Province of Grosseto
- Rentals with a balcony Province of Grosseto
- Family-friendly rentals Province of Grosseto
- Castle rentals Province of Grosseto
- Farm stay rentals Province of Grosseto
- Rentals with a washing machine and dryer Province of Grosseto
- Apartment rentals Province of Grosseto
- Bed and breakfasts Province of Grosseto
- Pet-friendly rentals Province of Grosseto
- Private suite rentals Province of Grosseto
- Townhouse rentals Province of Grosseto
- Rentals with a kayak Province of Grosseto
- Beachfront rentals Province of Grosseto
- Fitness-friendly rentals Province of Grosseto
- Waterfront rentals Province of Grosseto
- Guest house rentals Province of Grosseto
- Rentals with outdoor seating Province of Grosseto
- Rentals with an EV charger Province of Grosseto
- Luxury rentals Province of Grosseto
- Rentals with a patio Province of Grosseto
- Rentals with an accessible-height bed Province of Grosseto
- Rentals with lake access Province of Grosseto
- Cottage rentals Province of Grosseto
- Flat rentals Province of Grosseto
- House rentals Province of Grosseto
- Tent rentals Province of Grosseto
- Rentals with a hot tub Province of Grosseto
- Hotel 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
- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Giannutri
- Feniglia
- Gulf of Baratti
- Cala Violina
- Marina di Grosseto beach
- Kite Beach Fiumara
- Spiaggia di Capo Bianco
- Spiaggia Di Sansone
- Avignonesi Winery Fattoria Le Capezzine
- Cavallino Matto
- Cala Di Forno
- Spiaggia Marina di Cecina
- Santa Maria della Scala
- Spiaggia Di Barbarossa
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Zuccale
- Tenuta Le Velette
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- CavallinoMatto
- Spiaggia della Padulella
- Spiaggia di Cavo
- Things to do Province of Grosseto
- Food and drink Province of Grosseto
- Nature and outdoors Province of Grosseto
- Things to do Tuscany
- Sports activities Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Wellness Tuscany
- Tours Tuscany
- Sightseeing Tuscany
- Food and drink Tuscany
- Things to do Italy
- Nature and outdoors Italy
- Food and drink Italy
- Sports activities Italy
- Art and culture Italy
- Tours Italy
- Wellness Italy
- Sightseeing Italy
- Entertainment Italy