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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 favorite
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 stars3 months ago
We had a great time with the family in this peaceful little corner in the middle of nature! Isabella is a great host! thanks 😘 We recommend it!!
Guest favorite
Villa in Montepulciano
4.91 out of 5 average rating, 119 reviews

Villa in Montepulciano with Pool

MosesRating, 5 stars3 months ago
Alex, u show such hospitality to our family!! We love how well u maintained the place. The view from our hotel brings smile to my face every morning! It’s spectacular. I’ll definitely come back! Hope the price is reasonable the next time 🥰
Superhost
Home in Gaiole In Chianti
4.86 out of 5 average rating, 249 reviews

Charming estate with views

MoritzRating, 5 stars3 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.
Guest favorite
Villa in San Casciano in Val di Pesa
4.94 out of 5 average rating, 162 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

AmandaRating, 5 stars3 weeks ago
Incredible stay at Beatrice’s place. From booking to exit she had helped my group and I plan our stay in Tuscany finding wineries and vineyards to explore. She was so kind and pleasant to work with I would suggest her place to anyone! The kitchen was cozy and perfect for our group to spend time in while at the bnb. Every room was exactly as described. Perfect stay!
Guest favorite
Cottage in Geggiano
4.99 out of 5 average rating, 126 reviews

Villa di Geggiano - Guesthouse

GabrielRating, 5 stars1 month 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 favorite
Cottage in Castell'azzara
4.98 out of 5 average rating, 129 reviews

Your Private Tuscan Retreat

IliaRating, 5 stars1 month 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.
Guest favorite
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

PeterRating, 5 stars2 months ago
Very nice and clean appartment in a very quiet area. Only Met Gaston shortly since we were out all day visiting Tuscany with friends, But he was very Friendly. Will definitely come back

Family- and pet-friendly home rentals

Guest favorite
Apartment in Marciana
4.79 out of 5 average rating, 100 reviews

Casa Piccola

KarinRating, 5 stars6 months ago
We found the apartment very clean and as described, and the hosts were very friendly. They gave us tips for excursions upon arrival. Anna Maria and her husband have designed a little paradise here. If you are looking for peace, you will also find it in this beautiful environment. The terrace is not only perfect for sunsets, but also for the view of the starry sky! The space was sufficient for us with two children, as we were usually outside anyway. We can recommend the small shop in neighboring Colle d'Orano. We really enjoyed the week in Patresi!
Superhost
Farm stay in orbetello
4.63 out of 5 average rating, 112 reviews

Ground floor studio apartment in Farmhouse - pool

FlavioRating, 5 stars1 week ago
Massimiliano is very kind and very reserved.
Guest favorite
Condo in Cortona
4.98 out of 5 average rating, 129 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

John MarkRating, 5 stars2 weeks 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!
Guest favorite
Apartment in Montiano, Magliano in Toscana
4.98 out of 5 average rating, 44 reviews

Poggio Bestiale holiday home

ChiaraRating, 5 stars6 months ago
The accommodation is as described and perfect for a relaxing holiday. Great location to reach the Argentario and at the same time enjoy the return of a silence and a fantastic view. The apartment is very nice and clean, Denise is a superlative host, we were very very satisfied.
Superhost
Apartment in Volterra
5 out of 5 average rating, 4 reviews

APARTMENTS 3 people+ 4 people

KasiaRating, 5 stars31 months ago
Claudia is a great host, always very helpful and super nice. We felt very comfortable. The apartments have everything you need, the pool is great - very clean and with a wonderful view. The location is also great - in about 15 minutes you are in the Volterra and it only takes half an hour to get to San Gimignano. We will be happy to come back and thank you for the delicious oil and the beautiful vacation!
Guest favorite
Home in Subbiano
4.99 out of 5 average rating, 78 reviews

Romantic cosy flat - Toscana Italy

DavidRating, 5 stars4 months ago
This was exactly what we were looking for. Very peaceful and private with beautiful views. Lots of wonderful villages to visit and explore within a 30 minute drive. Norma made some great reservations for our anniversary dinner as well as a couple of great wine tours. She also gave us recommendations of which villages were best to visit and what to do there. We highly recommend doing the cooking lessons with her family. They are such a nice family and were very eager to show us how to cook a traditional Tuscan meal. Grandma really is an amazing cook. They even sat with us as a family to share what we had cooked. We have been to many AirBnB’s and Norma has been our best host by far. We would go back the next time we visit Tuscany. Dave and Liz
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
The only thing I could say negative is the lack of lighting for the kitchen and dining room. For the rest everything is perfect if you like the countryside decor:-)
Guest favorite
Condo in Asciano
5 out of 5 average rating, 162 reviews

Pink as the sunset sky

하늘Rating, 5 stars3 months ago
Famous small towns around Tuscany are expensive, but this is a place where you can fully enjoy the natural scenery of Tuscany at a reasonable price. The host was very friendly and the house was a very nice place to get a hands on experience of the farmhouse. It's an old brick house, but the antique interior and natural scenery were great.

Family-friendly home rentals with a pool

Guest favorite
Villa in Siena
4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

MarkRating, 5 stars4 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 favorite
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
Apartment in Montespertoli
4.89 out of 5 average rating, 9 reviews

12/14 pers,WiFi,Sw-pool,catering

MartinaRating, 5 stars23 months ago
The place is magnificent and very well kept, clean and super cozy. It's a little out of the way but we chose it just for the secluded location and surrounded by nature; in any case with a halfhour by car you can get to several wonderful places. Nicola was very kind and helpful. I highly recommend a stay here, it's refreshing!!
Guest favorite
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!
Superhost
Villa in Talla
4.91 out of 5 average rating, 23 reviews

Lovely villa heated outdoor pool & tennis court

LoriRating, 5 stars4 months ago
The villa exceeded our expectations. It was exceptionally clean and well cared for. Excellent amenities. Beautiful surroundings with olive and lemon trees. Cute little village nearby with an excellent restaurant. The host was very responsive. We had a bit of trouble finding the place but that might be more us than the directions. You definitely need a rental car Thank you for an amazing stay
Guest favorite
Farm stay in Pienza
4.93 out of 5 average rating, 169 reviews

Agriturismo Palazzi del Papa Val d 'Orcia Pienza

LeslieRating, 5 stars3 months ago
Nice agriturismo, very chill place and beautiful surroundings
Superhost
Home in Cortona
4.92 out of 5 average rating, 26 reviews

Beautifully restored villa with private pool

RoxarnaRating, 5 stars4 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 favorite
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

    $30 before taxes and fees

  • Total number of reviews

    510 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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