
Family-friendly vacation rentals in Province of Grosseto
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Top-rated family-friendly rentals in Province of Grosseto
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Family-friendly home rentals with a hot tub

Podere Ferranino #Cimabue Townhouse
Amazin relaxation! Great space, gorgeous view, and they even have an electric charging station!

Bellagatta, an Enchanting spot in Val d'Orcia
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!

Eco-friendly loft inside pinewood near the beach
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

Villa in Montepulciano with a Pool
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!

CasaBelvedere13 STAR Sea View Maremma Tuscany.
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!

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!

Charming House in Montepulciano
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!!

Tuscan country villa with private swimming pool
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

Sea, Relax, Park of the Maremma Alberese, Tuscany
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!

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.

Romantic apartment for two in beautiful Sorano
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!

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

Agriturismo Palazzi del Papa Val d 'Orcia Pienza
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!

Amazing view of Val d'Orcia Pienza
Very comfortable accommodations and gorgeous property and views

Montemassi, the Maremma that enchants - House of the Arts
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!

La Manonera Cottage for 2 people
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

Small cottage, swimming pool entirely private use
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!

CasaVIOLA Brunello vineyards
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!

agriturismo Torribasse
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.

Case Bianchi
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.

Beautiful tuscan country house
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.

Villa le Rocce - Apt Yellow (without kitchen)
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.

Mimosa Apartment - Poggio al Vento
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.

Tenuta La Fuga – Cottage with private pool
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!
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- 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
- Spiaggia Marina di Cecina
- Cala Di Forno
- Santa Maria della Scala
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Di Barbarossa
- Spiaggia Zuccale
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Tenuta Le Velette
- CavallinoMatto
- Spiaggia della Padulella
- Spiaggia di Cavo
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