Some info has been automatically translated. Show original language

Family-friendly vacation rentals in Grosseto

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

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 stars5 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.
Guest favorite
Farm stay in Sovicille
5 out of 5 average rating, 23 reviews

Tuscan Villa:Pool,Hot Tub,A/C,wi-fi,7bd near Siena

TimRating, 5 stars8 months ago
Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place
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
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 a Pool

MosesRating, 5 stars4 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, 252 reviews

Charming estate with views

Deise Rating, 5 stars1 week ago
The best BandB we ever stayed. I am a very OCD person and I was very impressed how spotless and polish the place was. Everything was carefully thought out. Everything you need is in the place. Bernadino and His wife Luciana were amazing. Providing us with homemade Italian food and taxi services. They were so friendly that I am happy coming back with my kids. The view was breathtaking. Absolutely loved everything.
Top guest favorite
Cottage in Geggiano
4.99 out of 5 average rating, 127 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 favorite
Cottage in Castell'azzara
4.98 out of 5 average rating, 132 reviews

Your Private Tuscan Retreat

ShaunRating, 5 stars4 days ago
Our stay at Riccardo & Kate's property was fantastic, the property is as described, the views were awesome. Riccardo was more than happy to help us with local recommendations & bookings when we needed help as we speak next to no Italian. The local town of Castell'Azzara is a beautiful place & the local people were very helpful at the Coop, bakery & restaurants.
Guest favorite
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

PeterRating, 5 stars3 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

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

La Maison di Monica & Simona

MaximeRating, 5 stars3 months ago
Monica is very welcoming. The value for money is very good. Be careful if you have small children because there are slightly steep stairs to access the accommodation.
Guest favorite
Apartment in Marciana
4.79 out of 5 average rating, 100 reviews

Small house

KarinRating, 5 stars7 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
4.64 out of 5 average rating, 115 reviews

Ground floor studio apartment in Farmhouse - pool

ValentinaRating, 5 stars2 weeks ago
Everything is beautiful! Clean and well equipped room, the kitchen with a view of the garden and the Maremma fields. We fell in love with it, highly recommended!
Top guest favorite
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 favorite
Apartment in Montiano, Magliano in Toscana
4.98 out of 5 average rating, 44 reviews

Poggio Bestiale Vacation Home

ChiaraRating, 5 stars7 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 stars32 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!
Superhost
Farm stay in Montepulciano
4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

SylvanaRating, 5 stars6 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:-)
Top guest favorite
Condo in Asciano
5 out of 5 average rating, 166 reviews

Pink like the sunset sky

AjitRating, 5 stars5 days ago
We had a wonderful time at Lucia’s place . The house is charming and very clean . It is in the heart of beautiful Tuscany and you have exceptional view from every window . Checkin was easy and host is very kind and responsive . Highly recommended for a wonderful experience of Tuscany .

Family-friendly home rentals with a pool

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

Medieval Cottage near Cortona

AnneRating, 5 stars43 months ago
Words can’t describe how beautiful this little restored village is - if you are seeking for a tasteful arranged place where you are all by yourself, surrounded by pure nature and a few other guests (that respect your privacy) this is where you should go. Highly recommended!!
Top guest favorite
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!
Superhost
Apartment in Gaiole In Chianti
4.68 out of 5 average rating, 22 reviews

Idyllic with shared pool in the heart of Chianti

GuidoRating, 5 stars7 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!
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 stars5 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, 22 reviews

Lovely villa heated outdoor pool & tennis court

LoriRating, 5 stars5 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 stars4 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 stars6 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
Townhouse in Barberino Tavarnelle
4.96 out of 5 average rating, 55 reviews

Restored Ancient Farmhouse

GiorgioRating, 5 stars5 months ago
The house was large and roomy and each room had a private bath with a good shower. The kitchen was well equipped. The hostess was extraordinarily generous with the little things she made available to us. We might have wanted to grill for a dinner but the outdoor grill was rather greasy and not appealing to use. The one drawback ( that was not her fault) was the horrible condition of the road leading to the house. All in all, a great stay.

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

    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

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Grosseto
  6. Family-friendly rentals