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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

MartinRating, 5 stars10 months ago
Sehr schönes Haus, landestypisch eingerichtet dabei aber trotzdem modern. Besonders gefallen haben und die Betten und die angenehme sanfte aber effektive Klimatisierung. Sehr geräumig, so dass ein Aufenthalt mit 4 Personen sehr angenehm möglich ist. Es gibt sogar eine Lademöglichkeit für E-Fahrzeuge.
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
A terrace features a simple table set with two white chairs, offering a view of the lush greenery beyond. An awning provides shade, while a blue sky with scattered clouds creates a serene atmosphere.
Apartment in Principina a Mare
5 out of 5 average rating, 6 reviews

Romantico Monolocale con vista sul Parco

ClaudiaRating, 5 stars3 days ago
siamo stati una settimana mio marito ed io e ci siamo trovati benissimo. la zona è tranquilla, ottima per riposare , ed è vicina alla spiaggia. alloggio pulito e con tutto ciò che poteva servire. le ragazze sono state tutte sempre molto disponibili e accoglienti. lo consiglio a chi vuole godersi giorni per recuperare, senza il caos del turismo .
Superhost
A spacious room features a four-poster bed draped with light fabric. An inviting dining area includes a wooden table and chairs. Exposed wooden beams and stone walls create a rustic charm, while large windows offer natural light and views of the outside landscape.
Apartment in Monterotondo Marittimo
4.76 out of 5 average rating, 37 reviews

Studio in Farmhouse, Swimming Pool, Restaurant.

ElenaRating, 5 stars2 months ago
Wir hatten eine schöne Zeit mit leckerem Essen und sehr freundlichen Gastgebern. Die Lage war wunderschön und die Zeit sehr entspannend. Vielen Dank :)
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 a Montepulciano con Piscina

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 STELLAvistaMare Maremma Toscana.

SuzanneRating, 5 stars1 month ago
Super mooie lokatie en een zeer sfeervol luxe huis met alle gemakken en gezelligheid Vele leuke plekjes in de tuin en dichtbij dorp en strand (10 min rijden) Isolina was erg lief en een erg fijne host. Ontzettende aanrader!
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
The stone villa is framed by lush greenery and overlooks a tranquil swimming pool. Large glass doors reflect the natural surroundings, enhancing the connection to the outdoors. The serene atmosphere is complemented by the native plants situated throughout the landscaped grounds.
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
The bedroom features light-colored walls and wooden flooring. A spacious bed is paired with a smaller bed suitable for a child. Natural light enters through a window adorned with light curtains. A mirror and dark wooden furniture complement the room's decor.
Home in Bagnore
4.93 out of 5 average rating, 177 reviews

La Casa del Valle

MattiaRating, 5 stars3 days ago
L’alloggio è stupendo, comodo, pulitissimo, e l’ host è stata gentilissima anche per quanto riguarda la flessibilità del check in! Un posto magnifico e raccomandato al cento per cento
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 stars5 days ago
Soggiorno delizioso e rilassante. Ricercavo un luogo nella campagna toscana a contatto con la natura: ho trovato esattamente ciò che desideravo. Comodo sia per recarsi al mare sia per camminare nel parco della Maremma. Sono stata così bene che desidero tornare appena possibile. E’ stato inoltre molto bello essere stati accolti dalla signora Maria, e’ stato come immergersi un pochino nella sua quotidianità, lavoro nei campi, gestire gli animali, la casa… Ringrazio l’host Fabio per la sua disponibilità! Soggiorno apprezzatissimo anche dal nostro cagnolino! Se dovessi usare una parola per descrivere il mio soggiorno: nutrita, sotto tutti i punti di vista!
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!
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

JulianeRating, 5 stars1 month ago
Wir hatten einen tollen Aufenthalt in dieser Unterkunft. Ruhig gelegen mit allem Komfort für eine entspannte Urlaubswoche in Val D’Orcia. Der Ausblick vom Garten des Grundstücks ist einfach nur wunderschön!
Top guest favorite
A wooden deck is surrounded by colorful flower pots and offers a table set for outdoor dining. The area is shaded by a pergola, providing a relaxed space to enjoy views of rolling hills and greenery in the distance.
Apartment in Montepulciano
4.92 out of 5 average rating, 157 reviews

Romantic apartment in a quite place

MelissaRating, 5 stars1 week ago
We had such a lovely stay at Paolo's place in Montepulciano! The location was beautiful and the pool was a highlight! They also had a little playground which was great for our toddler. Paolo was very welcoming and gave great recommendations for places to eat. They grow olive trees on the property, so they provided a little bottle of homemade olive oil in the kitchen, which was delicious! Thanks for having us and we hope to come back in the future!
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, la Maremma che incanta-Casa delle Arti

AuxaneRating, 5 stars8 months ago
Merveilleux appartement dans un bourg toscan au charme idilique! L'appartement est parfaitement équipé et on de sent directement comme à la maison. La region est magnifique et bien placée pour visiter la Toscane ! Dans le village, une boucherie/épicerie est accessible. Il y a aussi deux restaurants. Nous nous sommes rendus au "Al Castello" que nous recommandons pour des plats traditionnels ! Simona nous a toujours rapidement répondu lorsque nous avions des questions et l'arrivée/départ furent simplissimes ! Merci, nous reviendrons !
Guest favorite
An outdoor terrace features a glass dining table surrounded by four metal chairs, shaded by a large umbrella. Lush greenery and colorful flowers enhance the view, while decorative planters filled with plants add vibrancy to the space.
Home in Montalcino
4.97 out of 5 average rating, 149 reviews

Panoramic nest in Montalcino

JustinRating, 5 stars1 month ago
Fabulous location with scenic views in a beautiful town. Everything you need to do full self-catering, nice bed, good shower. Antonio was great in all our interactions, very quick to respond and helped us out with the parking a few times (you typically have to park 500m away, but it’s a lovely 10 min walk). We definitely plan to return and stay here again, maybe even next year!
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

ChantalRating, 5 stars2 weeks ago
Wir hatten eine tolle Zeit in dieser Unterkunft! Die Wohnung ist super ruhig und perfekt zum Abschalten. Liliana ist eine wundervolle Gastgeberin – sie hat uns sehr herzlich empfangen und sorgt dafür, dass man sich sofort wohl fühlt. Wir können überhaupt nichts bemängeln und würden jederzeit wiederkommen. Absolut empfehlenswert!

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

MartinRating, 5 stars5 days ago
Wir wurden mit frisch gebackenem Brot, selbst gemachtem Kuchen sehr herzlich empfangen. Das Olivenöl von Max und die selbstgemachte Marmelade waren auch sehr lecker 😋 Die Liegebetten waren total bequem. Der Pool wurde jeden Tag von Ivan gereinigt. 👍🏽 Olga hat uns sogar ein Backrohr organisiert 😊… Die Herzlichkeit von Olga und Max, die liebevoll gestaltete Unterkunft und all die kleinen Aufmerksamkeiten haben diesen Urlaub zu etwas ganz besonderen gemacht….danke 🥰Ulli & Martin
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
Die Unterkunft ist sehr schön inmitten der Landschaft gelegen, das Meer erreicht mit dem Auto in ca. 20 Minuten. Enrico gibt bei der Ankunft viele Tipps für Ausflüge und Unternehmungen in der Nähe. Die Unterkunft selbst war sauber und gut ausgestattet, man hat alles was man braucht.
Superhost
Villa in Seggiano
5 out of 5 average rating, 8 reviews

Case Bianchi

ThomasRating, 5 stars8 months ago
Das Haus ist sehr schön und rhuig gelegen, in einem sehr guten Zustand und top eingerichtet. Man braucht unbedingt ein Auto da Geschäfte, Restaurants und Cafes etwas weiter weg sind. Trotz gemischten Wetterbedingungen hatten wir einen sehr schönen Aufenthalt. Die schönen Tage waren wir Wandern, Fahrradfahren in der Maremma oder baden am Meer. Das naheliegende Daniel Spöri-Museum ist auch sehr empfehlenswert. Bei Regen haben wir in der gut ausgestatteten Küche ausgiebig gekocht und bei Kaminfeuer die gute DVD Musik- und Film-Auswahl genossen. Rundum für uns (5) ein perfekter Kurzurlaub.
Superhost
An inviting saltwater pool is surrounded by landscaped gardens featuring native greenery. Lounge chairs are placed nearby, offering a comfortable spot to relax. A rustic stone farmhouse is visible in the background, complementing the serene countryside setting.
Villa in Castiglione d'Orcia
5 out of 5 average rating, 11 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

MiaRating, 5 stars1 month ago
We were looking for a villa that had plenty of space for my husband and I with our 3 adult kids and this villa was perfect! We all had our own bedrooms and private bathrooms. The villa was in the idyllic peaceful Tuscan countryside surrounded by rolling hills, wine vineyards and olive trees with distant views of castles. It is absolutely gorgeous! Alessandro, the owner of the villa met us upon check in. The property has been in his family for hundreds if years. He was incredibly kind and generous, leaving an abundant amount of fruit, several bottles of wine from his vineyard and beautiful fresh flowers in every room. He was always available to answer any questions and make recommendations. Anke, the property manager, was excellent and responsive. Promptly answering my questions prior to the trip and proactively giving us wonderful recommendations. Highlights were truffle hunting Il Podere Castle, Umbria Olive oil tour and Banfi Castle wine tasting. Memories to last a lifetime! ❤️
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

LukasRating, 5 stars1 month ago
Das Haus ist schön und sehr gross. Es liegt etwas ausserhalb von Buonconvento und bietet absolute Privatsphäre. Ein Auto ist von Vorteil. Die Zimmer sind grosszügig, es gibt Mückennetze über allen Betten und genügend Badezimmer und WCs für alle. Generell ist das Haus sehr gut ausgestattet, sowohl in der Küche als auch sonst. Der Pool ist etwas erhöht, schön, gross, mit natürlichem Schatten rundherum und bietet eine herrliche Aussicht auf die umliegende Landschaft. Im riesigen Garten kann man Essen, Verweilen, Spielen... Es gibt sogar einen kleinen Basketball-Court. Aber Achtung: Gleich nebenan gibt es wilde Brombeeren und der Ball kann verloren gehen :) In Buonconvento gibt es einen Coop, eine feine Gelateria und eine gutes Caffé mit den berühmten und feinen Produkten von Le Dolcezze di Nanni. Für eine gute Pizza lohnt sich die Fahrt ins Restaurant Mulinum etwas ausserhalb, sie haben eine eigene Mühle und verarbeiten ihr eigenes Getreide. Wir können das Haus sehr empfehlen.
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
Punto forte della camera è la vista panoramica dal terrazzino privato. Camera come in foto. Piccola ma ben strutturata. Fabrizio e Francesco sono stati sempre molto disponibili nel fornire indicazioni e nel dare supporto alle esigenze di check in e check out. Lo Scooter a disposizione degli ospiti è un servizio davvero utile.
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

Appartamento Mimosa - 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.

Destinations to explore