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Family-friendly holiday 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
Apartment in San Giovanni d'Asso
5 out of 5 average rating, 20 reviews

Podere Ferranino #Cimabue Townhouse

CoreyRating, 5 stars1 week ago
Amazin relaxation! Great space, gorgeous view, and they even have an electric charging station!
Guest favourite
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
4.65 out of 5 average rating, 37 reviews

Eco-friendly loft inside pinewood near the beach

MariellaRating, 5 stars2 months ago
Lucia was always very kind and welcoming. The property is very organized, suitable for everyone. Also perfect for families, a lot of care for the spaces and accessories for children. The courtyard with breakfast bar is also very nice. We had a great time.
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 125 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
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 favourite
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 favourite
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
Holiday home in Saturnia
4.77 out of 5 average rating, 13 reviews

Tuscan country villa with private swimming pool

SeanRating, 5 stars11 months ago
Fantastic abode hidden below the village of Saturnia. The property is fantastic, and has sunshine all day beating down on the garden and pool area. The house has everything you'd need, well kitted out kitchen, and all bedrooms are en-suite. AC worked well, so good sleeping wasn't lacking. The outdoor grill area and living room were also great, especially at night while watching the stars and listening to the nature all around. And for our group, which included 5 kids and a couple of digital nomads, the wi-fi kept up to keep everyone satisfied. I'd stay again in a heartbeat and look forward to being back in Saturnia.

Family- and pet-friendly home rentals

Guest favourite
Condo in Grosseto
4.82 out of 5 average rating, 104 reviews

Sea, Relax, Park of the Maremma Alberese, Tuscany

BiancaRating, 5 stars1 day 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 great time that I want to go 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 little dog! If I had to use one word to describe my stay: nourished, in every way!
Superhost
Farm stay in Provincia di Siena
4.87 out of 5 average rating, 115 reviews

Spigo - Indipendent Cottage Zampugna

BrittanyRating, 5 stars1 month ago
Riccardo is a lovely host with a wonderful location. It was everything we could have hoped for. We could not have asked for a better stay.
Top Guest favourite
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
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 favourite
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
Guest favourite
Farm stay in Pari
4.84 out of 5 average rating, 241 reviews

lo Studiolo between Siena and Grosseto

AfifRating, 5 stars3 weeks ago
Staying at Lorenzo’s place was a really nice experience. You feel the warmth of the hosts from the moment you step in. The studio was what we expected from a house in the countryside. The garden and outdoor areas are very nice and accessible to all guests. The highlight of our stay was the dinner in Lorenzo and Maria Garcia’s house with the other guests, a real italian experience. They really made us feel like we are having dinner with our family, which was a very nice way to end our trip!
Top Guest favourite
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
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
Cottage in Roccalbegna
4.91 out of 5 average rating, 76 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
Farm stay in Castelnuovo dell’Abate
4.88 out of 5 average rating, 67 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 favourite
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.
Superhost
Farm stay in Pienza
4.81 out of 5 average rating, 170 reviews

Vacation in Piandimaggio in Val d'Orcia.

BlakeRating, 5 stars1 week ago
Great place and great host 🧡
Guest favourite
Villa in Buonconvento
5 out of 5 average rating, 11 reviews

Beautiful tuscan country house

LukasRating, 5 stars1 month ago
The house is beautiful and very big. It is located just outside of Buonconvento and offers complete privacy. A car is an advantage. The rooms are spacious, there are mosquito nets above all beds and enough bathrooms and toilets for everyone. In general, the house is very well equipped, both in the kitchen and otherwise. The pool is slightly elevated, beautiful, large, with natural shade all around and offers a magnificent view on the surrounding countryside. In the huge garden you can eat, linger, play... There is even a small basketball court. But beware: right next door there are wild blackberries and the ball can be lost :) In Buonconvento there is a coop, a fine gelateria and a good coffee with the famous and fine products of Le Dolcezze di Nanni. For a good pizza, the drive to the Mulinum restaurant is worth it a little outside, they have their own mill and process their own grain. We highly recommend the house.
Superhost
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 favourite
Apartment in Castiglione d'Orcia
4.99 out of 5 average rating, 68 reviews

Mimosa Apartment - Poggio al Vento

PaolaRating, 5 stars4 weeks 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.

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