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Family-friendly vacation rentals in Province of Grosseto

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Province of Grosseto family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A bright living area features a wooden table with a wine bottle and glass in the foreground. Large glass doors open to a patio, revealing countryside views and two outdoor chairs facing the tranquil landscape.
Apartment in San Giovanni d'Asso
5 out of 5 average rating, 20 reviews

Podere Ferranino #Cimabue Townhouse

CoreyRating, 5 stars2 weeks ago
Amazin relaxation! Great space, gorgeous view, and they even have an electric charging station!
Guest favorite
A charming corner of the property is adorned with bright pink flowers and framed by the rustic building. The view extends to rolling hills in the distance under a clear blue sky, with greenery surrounding a stone patio area in the foreground.
Villa in Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!
Superhost
Apartment in Principina a Mare
4.66 out of 5 average rating, 38 reviews

Eco-friendly loft inside pinewood near the beach

VeronicaRating, 5 stars1 month ago
Lucia was very helpful and well arranged with us, friendly and friendly with children. Both managers have helped me with great kindness to solve some personal difficulties
Guest favorite
The villa is set against a backdrop of rolling hills and gardens. A large pool is visible in the foreground, featuring a circular shape and steps leading into the water. The stone structure with a tiled roof complements the natural surroundings.
Villa in Montepulciano
4.91 out of 5 average rating, 126 reviews

Villa in Montepulciano with a Pool

SantiagoRating, 5 stars1 week ago
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!
Superhost
A covered terrace features a wooden dining table surrounded by chairs, set against a backdrop of lush greenery. Natural light filters through the roof, casting shadows on the stone floor. The space offers a relaxing view of the garden and hillside beyond.
Home in Zona 167 Scarlino
4.91 out of 5 average rating, 32 reviews

CasaBelvedere13 STAR Sea View Maremma Tuscany.

SuzanneRating, 5 stars1 month ago
Super nice location and a very cozy luxury house with all the comforts and coziness Many nice places in the garden and close to the village and beach (10 min drive) Isolina was very sweet and a very nice host. Highly recommended!
Guest favorite
A ground-level countryside dwelling is presented with natural stone pathways and wooden shutters. Potted plants are positioned near the entrance. The exterior is complemented by expansive windows, providing views of the surrounding landscape under a clear blue sky.
Home in Catabbio
4.89 out of 5 average rating, 159 reviews

Country house La Meria

AlexRating, 5 stars2 months ago
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!
Top guest favorite
An ancient stone well is positioned in the foreground, showcasing intricate carvings and a circular top. In the background, an impressive stone building features a tower and windows, accented by flags. The scene captures the historical charm of Montepulciano's central square under a clear blue sky.
Apartment in Montepulciano
4.92 out of 5 average rating, 142 reviews

Charming House in Montepulciano

KirstenRating, 5 stars3 months ago
Our family loved staying in Fernanda’s apartment! My husband and I had visited Montepulciano two years ago, stayed at Fernanda’s place and loved it so much we came back with our three boys. Everything is so lovely and welcoming and Fernanda is the best hostess. She even made local dinner reservations for us. Thank you for everything, Fernanda!!
Superhost
A villa made from natural stone is set amidst a lush garden, featuring large windows that reflect the evening light. An irregularly shaped pool is positioned in the foreground, blending seamlessly with the surrounding greenery and offering views of the peaceful landscape.
Vacation home in Saturnia
4.79 out of 5 average rating, 14 reviews

Tuscan country villa with private swimming pool

MadeleineRating, 5 stars3 weeks ago
What an amazing and beautiful home! We loved our stay here with our family and enjoyed a delicious meal prepared by Susanna and Tiziano for my sisters birthday dinner. Gorgeous location, great pool, really fun art all over the entire house that’s been restored but full of character. Plus it’s just 5 mins and your at the hot springs or restaurants. We can’t it to go back!

Family- and pet-friendly home rentals

Guest favorite
A spacious two-story building is highlighted, featuring a welcoming facade with several windows and a central entrance. Lush green trees and well-maintained grass surround the property, and a gazebo is positioned nearby, complementing the natural setting in the background.
Condo in Grosseto
4.82 out of 5 average rating, 104 reviews

Sea, Relax, Park of the Maremma Alberese, Tuscany

BiancaRating, 5 stars4 days ago
Delightful and relaxing stay. I was looking for a place in the Tuscan countryside in contact with nature: I found exactly what I wanted. Convenient both for going to the sea and for walking in the Maremma park. I had such a good time that I want to come back as soon as possible. It was also very nice to have been welcomed by Mrs. Maria, it was like immersing yourself a little in her daily life, working in the fields, managing the animals, the house... I thank the host Fabio for his availability! A stay that was also much appreciated by our dog! If I had to use one word to describe my stay: nourished, in all respects!
Guest favorite
A hammock hangs gently between trees in a spacious garden, surrounded by large volcanic rocks. Sunlight filters through the lush greenery, creating a serene outdoor space ideal for relaxation. Wooden stools and natural landscaping enhance the tranquil atmosphere.
Home in Vivo d’Orcia
4.95 out of 5 average rating, 139 reviews

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

DianeRating, 5 stars3 weeks ago
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.
Top guest favorite
A small staircase leads up, surrounded by textured white walls and terracotta tiles. A window with wooden frames allows natural light to enter, offering a view of greenery outside. The décor includes a rustic light fixture and an ornamental mirror, enhancing the inviting atmosphere.
Apartment in Sorano
4.73 out of 5 average rating, 108 reviews

Romantic apartment for two in beautiful Sorano

BethRating, 5 stars3 weeks ago
This place was magical. I fell asleep every night listening to the waterfall in the ravine. Town was a fairytale spot. I never got tired of exploring the beautiful, twisting old streets. Property was just as promised. Rikke went so far above and beyond to make me feel welcome, even arranging a money saving ride to the train station for me. Great experience!
Superhost
An outdoor area features a stone patio with a small dining table and chairs shaded by a large umbrella. Potted plants surround the space, while a swimming pool reflects the blue sky, offering scenic views of the hills and greenery in the distance.
Home in Sorano
4.8 out of 5 average rating, 128 reviews

Lovely home in villa with garden and pool

JoshRating, 5 stars2 weeks ago
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.
Guest favorite
An aerial view captures the agriturismo's spacious grounds, featuring a inviting swimming pool surrounded by sun loungers. Lush green lawns and well-maintained gardens frame the rustic stone buildings, which offer a peaceful retreat amidst scenic farmland.
Farm stay in Pienza
4.94 out of 5 average rating, 172 reviews

Agriturismo Palazzi del Papa Val d 'Orcia Pienza

EleanorRating, 5 stars1 month ago
We had an amazing week long stay!! Sabrina is a fantastic host! The apartment was SO clean and comfortable and had everything we needed. Breakfast each morning was very yummy and fresh! We did the dinner one night and it was so amazing! Location is great too. Easy drive to many close by towns, grocery stores, and restaurants. The property is beautiful with lots of flowers. A little too cold for the pool during our stay but our kids loved the swing set and teeter totter. Absolutely recommend staying here!
Guest favorite
The spacious kitchen and living area features a central island counter with a wine bottle and glasses. Natural light floods the space through multiple windows, illuminating the dining table and a cozy seating area with a sofa. A rustic ceiling enhances the homey ambiance.
Condo in Pienza
4.91 out of 5 average rating, 99 reviews

Amazing view of Val d'Orcia Pienza

AnneRating, 5 stars1 month ago
Very comfortable accommodations and gorgeous property and views
Top guest favorite
An outdoor terrace area is presented, featuring a green wooden table surrounded by two white chairs. A large white umbrella provides shade, while various potted plants add greenery. The stone wall of the building and steps in the background contribute to the rustic ambiance.
Apartment in Montemassi
4.92 out of 5 average rating, 106 reviews

Montemassi, the Maremma that enchants - House of the Arts

AuxaneRating, 5 stars8 months ago
Wonderful apartment in a Tuscan village with idyllic charm! The apartment is perfectly equipped and it feels like home. The region is beautiful and well located for visiting Tuscany! In the village, a butcher/grocery store is accessible. There are also two restaurants. We went to "Al Castello" which we recommend for traditional dishes! Simona always responded quickly to us when we had any questions and check-in/checkout were very simple! Thank you, we'll be back!
Superhost
The image presents a scenic view of a rustic stone cottage nestled within lush greenery. Tall trees frame the space, with vibrant flowers in the foreground. The pathway leading to the house invites exploration, complemented by the tranquil countryside ambiance.
Farm stay in Montepulciano
4.78 out of 5 average rating, 264 reviews

La Manonera Cottage for 2 people

StevenRating, 5 stars1 week ago
Liliana, was a brilliant sweet host. Extremely helpful and kind. She has a beautiful super friendly dog, who loves attention! The property was in such a lovely location, stunning views and so peaceful. The apartment was cosy and had everything you need. I would recommended staying here. We had a lovely stay!

Family-friendly home rentals with a pool

Superhost
A rustic stone house is set against a backdrop of lush trees, featuring a terrace with sun loungers arranged around a central swimming pool. The building's earthy tones complement the natural surroundings, while a chimney adds a touch of charm to the exterior.
Cottage in Roccalbegna
4.91 out of 5 average rating, 77 reviews

Small cottage, swimming pool entirely private use

MilliRating, 5 stars1 week ago
What a fabulous place - if you want to escape from it all, this is the place to come! Love the private pool too! Air conditioning in the bedroom was very good and appreciated. Olga and Max were very accommodating and answered questions very quickly. Maybe consider installing a BBQ outside the house otherwise could not fault it and we cannot wait to return!
Superhost
A serene hillside retreat is set amidst lush vineyards, showcasing a rustic building adjacent to a sparkling pool. The landscape features rolling hills and a vibrant sky at dusk, providing a tranquil backdrop that emphasizes the peaceful surroundings.
Farm stay in Castelnuovo dell’Abate
4.88 out of 5 average rating, 68 reviews

CasaVIOLA Brunello vineyards

IhorRating, 5 stars2 weeks ago
This is an incredible villa in Tuscany, my girlfriend and I are excited about our vacation here! It’s a pity that we booked for only two days, next time we will book for a longer period. Definitely recommend!
Top guest favorite
A hammock is gently suspended between wooden posts, surrounded by a lush green lawn and trees. Colorful flower pots are positioned nearby, and charming rustic buildings are visible in the background under a clear blue sky.
Farm stay in Magliano in Toscana
5 out of 5 average rating, 31 reviews

agriturismo Torribasse

SophieRating, 5 stars9 months ago
The property is very nicely located in the middle of the countryside, the sea can be reached in about 20 minutes by car. Enrico gives many tips for excursions and activities nearby upon arrival. The place itself was clean and well equipped, you have everything you need.
Superhost
Villa in Seggiano
5 out of 5 average rating, 8 reviews

Case Bianchi

JulianeRating, 5 stars3 weeks ago
We had a great time! Super clean and spacious house with a nice outdoor area. Constanze was always super helpful and responded quickly. But be aware, you need a car and restaurants and supermarkets are not in walking distance. Thanks a lot for having us.
Guest favorite
A rustic Tuscan farmhouse, restored with care, features a tall tower and expansive windows. Surrounding greenery includes cypress trees and shrubs, complementing the natural landscape. The lawn offers open space for relaxation, enhancing the serene atmosphere of the property.
Villa in Buonconvento
5 out of 5 average rating, 12 reviews

Beautiful tuscan country house

AlexRating, 5 stars3 days ago
An incredible, beautiful house where you’ll feel right at home. The villa is spacious and welcoming, perfect for cooking and relaxing with friends. My only suggestions would be the need for fans in the bedrooms as without AC it gets quite warm during those hot evenings.
Superhost
Four glasses of drinks are presented on a wooden table beside a serene swimming pool. The view showcases the calming blue sea and a clear sky, enhancing the tranquil atmosphere of the location.
Apartment in Isola del Giglio
4.78 out of 5 average rating, 191 reviews

Villa le Rocce - Apt Yellow (without kitchen)

AndreaRating, 5 stars1 month ago
The room's highlight is the panoramic view from the private terrace. Room as pictured. Small but well-structured. Fabrizio and Francesco were always very helpful in providing directions and in supporting check-in and check-out needs. The Scooter available for guests is a really useful service.
Top guest favorite
An outdoor swimming pool is centered in the image, surrounded by a spacious terrace. Umbrellas stand nearby, and a view of rolling hills and distant mountains can be seen in the background under a clear blue sky.
Apartment in Castiglione d'Orcia
4.99 out of 5 average rating, 68 reviews

Mimosa Apartment - Poggio al Vento

PaolaRating, 5 stars1 month ago
We had an absolutely wonderful stay at this Airbnb! The space was exactly as described—clean, cozy, and thoughtfully decorated, with all the amenities we needed for a comfortable visit. The bed was super comfortable, and I really appreciated touches like fresh towels and the equipped kitchen. Our host Roberto was exceptional—friendly, responsive, and genuinely welcoming. He made check-in seamless. The location was perfect—quiet and peaceful, yet close enough to everything we wanted to see and do. I would definitely stay here again and highly recommend it to anyone visiting the area. Thanks again for such a lovely stay that we will never forget, Roberto! Wish you all the best.
Guest favorite
A private pool is set within a verdant lawn, surrounded by tall cypress trees and leafy shrubs. Sun loungers are arranged for relaxation next to the pool, while a stone house with a terracotta roof stands in the background under a clear blue sky.
Farm stay in Camigliano
4.96 out of 5 average rating, 85 reviews

Tenuta La Fuga – Cottage with private pool

KellyRating, 5 stars2 weeks ago
From check in to check out, everything was amazing! The home was so comfortable and the rooms were large and nicely furnished. The grounds were well maintained with planters lining the terrace. The terrace overlooks the vineyards. The views were spectacular! We were provided a selection of wines that we could enjoy and purchase at the end of our stay. In addition, we were able to take advantage of enjoying a meal prepared by Chef Francesco at the property. It was perfect! We highly recommend Giovanni’s listing!

Destinations to explore