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Family-friendly vacation rentals in Grosseto

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Grosseto family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars4 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Superhost
Home in Campo nell'Elba
4.9 out of 5 average rating, 145 reviews

Relax in the countryside near the sea( Lavanda )

LorianneRating, 5 stars4 months ago
Nous avons passé un super séjour en famille dans ce petit coin paisible au milieu de la nature ! Isabella est une excellente hôtesse! merci 😘 On recommande!!
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 119 reviews

Villa a Montepulciano con Piscina

MichalRating, 5 stars4 months ago
Willa jest cudowna, duża i przestronna. położona w cichym miejscu z pięknym widokiem na winogronowe drzewa, góry Toskanii. Jeśli chcesz w pełni poczuć atmosferę pięknej Toskanii, ta willa jest idealnym wyborem. Byliśmy tam rodziną z trójką dzieci i dzieciaki nie chciały wyjść z basenu który był podgrzewany do godziny 18. Gospodarz był bardzo uprzejmy i pomocny. Dziękujęmy i już nie możemy się doczekać kiedy znów wrócimy !
Superhost
Home in Gaiole In Chianti
4.86 out of 5 average rating, 250 reviews

Charming estate with views

MoritzRating, 5 stars4 months ago
We loved Bernardino's place. It was super cozy, the garden and whirlpool were amazing. The kitchen had everything we needed. And Bernardino was super helpful with tips and answers to all our questions. Highly recommend if you're looking for a remote place to enjoy Tuscany.
Top guest favourite
Cottage in Geggiano
4.99 out of 5 average rating, 126 reviews

Villa di Geggiano - Guesthouse

GabrielRating, 5 stars2 months ago
Vila Di Geggiano was everything we were expecting it to be and more. We simply loved the place, quiet and very comfortable, set in the middle of a beautiful Toscana. The guest apartment is located by the side of the Main House, a historical summer palace with a deep history behind it. Andrea, our host, gave us a personal tour of the main house, filled with great stories about his ancestors. The house has been in Andrea´s family since the 1500s! If you are looking to spend some quiet days enjoying the great food and wine of Toscana in a relaxed, unique and comfortable space, Vila di Geggiano is a great destination for you.
Guest favourite
Cottage in Castell'azzara
4.98 out of 5 average rating, 130 reviews

Your Private Tuscan Retreat

IliaRating, 5 stars2 months ago
A beautiful, peaceful spot in the heart of Tuscany - perfect for a relaxing getaway! Riccardo and Kate are wonderful hosts who made everything easy and made us feel right at home. The house is cozy and well-equipped with everything you could need, from a comfy bed and a fully stocked kitchen to a sauna and an amazing open-air hot tub. Also, one of the bonuses of this location is very low air pollution, so stargazing at night was a real highlight of our trip. Would definitely recommend for anyone looking to unwind and enjoy the beauty of Tuscany.
Top guest favourite
Home in Simignano
4.96 out of 5 average rating, 110 reviews

Casa al Gianni - Il Fienile di Simignano

vilbecky貝小琪Rating, 5 stars1 month ago
It’s a very nice villa we love it!
Guest favourite
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

Michelangelo LiburdiRating, 5 stars3 months ago
se cercate un posto tranquillo e facile da raggiungere, è il posto ideale. proprietari disponibili ad ogni evenienza, appartamento corrispondente alla descrizione e super pulito. grazie Gaston per la gentilezza e disponibilità dimostrata, super consigliato

Family- and pet-friendly home rentals

Superhost
Apartment in Sasso Pisano
4.78 out of 5 average rating, 187 reviews

La Maison di Monica & Simona

MaximeRating, 5 stars2 months ago
Monica est très accueillante. Le rapport qualité prix est très correcte. Attention si vous avez des enfants en bas âge car il y a des escaliers un peu raide pour accéder au logement.
Superhost
Farm stay in orbetello
4.64 out of 5 average rating, 114 reviews

Ground floor studio apartment in Farmhouse - pool

GiovinaRating, 5 stars1 week ago
Alloggio immerso nella campagna Maremmana a pochi minuti di auto dal mare, posizione perfetta. Alloggio molto pulito con tutto l'essenziale, comodo e confortevole. Massimiliano è un host molto reattivo nelle comunicazioni e disponibile. La colazione con cestino da gustare in giardino è una vera coccola. Consigliatissimo.
Superhost
Vacation home in Porto santo Stefano
4.83 out of 5 average rating, 35 reviews

Villino Mare nel sole

BrigitteRating, 5 stars7 months ago
Wir hatten eine wunderbare Woche im Ferienhaus von Ale, mit direktem weitem Blick aufs Meer und 2 Inseln. Ale sandte eine sehr genaue Beschreibung, wie man zu Ihr findet, incl. Fotos von den wichtigsten Abzweigstellen. Es war einfach zu finden für uns. Wir waren mit einem SUV und 2 E-Bikes da, den Parkplatz zu unserem Chalet konnten wir damit gut erreichen, auch die etwas steilere Straße runter zum Chalet. Für alle Fahrzeuge, die keinen höheren Radstand haben, gibt es oberhalb von Ales Haus einen Parkplatz, man ist in 3 -4 Minuten zu Fuß unten. Ale hieß uns herzlich willkommen, und versorgte uns mit Tips für Restaurants und Strände in der näheren Umgebung. Unser Chalet hatte alles, war wir brauchten zu zweit. 2 Terrassen, davon eine mit Outdoorküche, im Schlafzimmer gibt es eine Klimaanlage, die wir zum Einschlafen nutzten. Den Blick über das Meer bis zu den Inseln haben wir von morgens bis abends genossen, es gab immer etwas zu sehen. Wir hatten eine tolle Zeit, danke Ale!
Top guest favourite
Condo in Cortona
4.98 out of 5 average rating, 129 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

John MarkRating, 5 stars1 month ago
We had an incredible stay at Clara's property in Cortona! The highlight of our trip was definitely the visit to the farm, which was not only fun but also deeply meaningful. We loved learning about the local way of life. Our host, Clara, was warm, welcoming, and extremely helpful throughout our stay. They went above and beyond to ensure we felt at home and had everything we needed. The property itself was clean, comfortable and well-located. We would highly recommend to anyone looking for an authentic and unforgettable experience in Cortona. Grazie mille, Clara for sharing your little slice of heaven with us!
Top guest favourite
Apartment in Montiano, Magliano in Toscana
4.98 out of 5 average rating, 44 reviews

Casa vacanza Poggio Bestiale

ChiaraRating, 5 stars6 months ago
L’alloggio è conforme alla descrizione e perfetto per una vacanza in assoluto relax. Posizione ottimale per raggiungere l’Argentario e nel contempo godere al rientro di un silenzio ed un panorama fantastico. L’appartamento è molto curato e pulito, Denise è un host superlativa, siamo stati molto molto soddisfatti.
Superhost
Apartment in Volterra
5 out of 5 average rating, 4 reviews

APPARTAMENTI 3 persone+ 4 persone

KasiaRating, 5 stars32 months ago
Claudia ist eine tolle Gastgeberin, immer sehr hilfsbereit und super nett. Wir haben uns sehr wohl gefühlt. Die Appartements haben alles was man braucht, das Pool ist super - sehr sauber und mit einem wunderbaren Blick. Die lage ist auch top - in etwa 15 Minuten ist man in der Volterra und bis zu San Gimignano braucht man nur eine halbe Stunde. Wir kommen sehr gerne wieder und bedanken uns für das leckere Öl und den schönen Urlaub!
Superhost
Farm stay in Montepulciano
4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

SylvanaRating, 5 stars5 months ago
Le seul chose que je pourrais dire de négatif c’est le manque d’éclairage pour la cuisine et salle à manger . Pour le reste tout est parfait si on aime le décor de la campagne:-)
Top guest favourite
Condo in Asciano
5 out of 5 average rating, 163 reviews

Rosa come il cielo al tramonto

LorenzoRating, 5 stars2 months ago
Host gentile e disponibile, appartamento pulito e molto bello, zona splendida e soggiorno piacevole.

Family-friendly home rentals with a pool

Superhost
Apartment in Cortona
4.6 out of 5 average rating, 5 reviews

Medieval Cottage near Cortona

TommasoRating, 5 stars43 months ago
Un borgo meraviglioso immerso nel verde ma con tutte le comodità per trascorrere giornate all'insegna del relax e della tranquillità. Il borgo è stato ristrutturato in modo perfetto, lasciando intatto lo stile delle strutture. Gli appartamenti sono attrezzati con tutto il necessario e appena si mette piede fuori da casa si gode dei colori e dei suoni della natura, con la possibilità di fare anche un bel tuffo in piscina. Molto buono anche il ristorante e piacevolissima la compagnia dei cinghiali che si affacciano di tanto in tanto per un saluto. Davvero una bella scoperta!
Top guest favourite
Villa in Siena
4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

MarkRating, 5 stars5 months ago
We booked Villa Montechiarone as part of our wedding at Montechiaro Organic Winery to house a group of 7 guests. The property sits around 500m from the winery itself, with views out over the Tuscan countryside, it's a breathtaking location and the villa itself is an incredible space. There are 2 huge indoor living areas, a well equipped kitchen, 4 spacious bedrooms and an outdoor covered terrace, as well as the garden and pool area. There is real character in the property in the way it is decorated as well as the imposing facade of the building itself. The pool area is spacious and well placed to take in the most of the view, and there is a car port with parking for at least 4 cars covered, with plenty more room if required beyond. Overall perfect for housing our guests who had a great experience and were very thankful for the help whilst checking out also!
Guest favourite
Apartment in Gaiole In Chianti
4.76 out of 5 average rating, 21 reviews

Idyllic with shared pool in the heart of Chianti

GuidoRating, 5 stars6 months ago
Heidi's apartment is situated in a larger complex on the outskirts of the village, just a short walk from the town center where you can find a church, a mini supermarket, bars, and a popular restaurant that is always fully booked. The village is ideally located in the heart of Chianti, making it a perfect starting point for exploring the region. You can drive along one of the scenic, winding roads to a wine tasting event, enjoy a bike ride through the picturesque countryside, or visit nearby cities like Siena or Florence (Firenze). One of the highlights of the apartment is the spacious swimming pool (1.35 m deep), which is perfect for cooling off during the hot summer days, especially if you have kids. The apartment itself is well-equipped, ensuring a comfortable stay. Communication with Heidi is easy and friendly. She provides detailed information on the check-in and check-out procedures, as well as instructions for using various amenities in the complex. We enjoyed our stay!
Superhost
Home in Gaiole in Chianti
4.8 out of 5 average rating, 100 reviews

loft nel cuore del chianti toscano

CharlotteRating, 5 stars5 months ago
We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars4 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Guest favourite
Farm stay in Pienza
4.93 out of 5 average rating, 169 reviews

Agriturismo Palazzi del Papa Val d'Orcia Pienza

RenatoRating, 5 stars4 months ago
host magnifici, ci hanno aiutato nelle richieste, sempre disponibili. la casa era come descritta e molto confortevole. Grazie
Superhost
Home in Cortona
4.92 out of 5 average rating, 26 reviews

Beautifully restored villa with private pool

RoxarnaRating, 5 stars5 months ago
Thank you for allowing us to stay at your wonderful accommodation. This was the best place to celebrate my 50th birthday. What wonderful accommodation, facilities and the surrounds of Tuscany. Thank you for your lovely hospitality and making us feel so welcome. Roxy
Guest favourite
Home in Orvieto
4.82 out of 5 average rating, 22 reviews

House with private pool, air conditioning

FionaRating, 5 stars7 months ago
We were a family of 5 with two 20 year old boys and an eleven year old girl. We loved the homely feel of the farmhouse. It had everything we needed for our 10 day break. The gardens and pool were amazing and we loved the two different sitting areas. If you are looking for somewhere to get away from it all then this is a great option. There are a few nice restaurants within a ten minute drive and the towns of Orvieto and Bolcina were great to visit. We also used the train service to go to Rome which was very easy. You definitely need a car when staying here. Andrea was friendly, very helpful and on hand if you needed anything. Would definitely recommend this fantastic holiday home.

Quick stats about vacation rentals that are family-friendly in Grosseto

  • Total rentals

    40 properties

  • Nightly prices starting at

    $43 CAD before taxes and fees

  • Total number of reviews

    480 reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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