Some info has been automatically translated. Show original language

Family-friendly holiday 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 favourite
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars6 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, 146 reviews

Relax in the countryside near the sea( Lavanda )

AntonelloRating, 5 stars6 days ago
Isabella is a nice and helpful person, she welcomed us to her beautiful villa and immediately put us at ease. Great tips on places to visit and where to eat. The accommodation has all the comforts, beautiful salt pool, unfortunately not available since the season has not yet started. I'll definitely be back, thanks for everything Isabella!
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 121 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars4 days ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Superhost
Home in Gaiole in Chianti
4.86 out of 5 average rating, 254 reviews

Charming estate with views

BriRating, 5 stars4 days ago
We had such a lovely stay at Bernardino’s villa! He greeted us when we arrived and made sure we had everything we needed. The home is very charming and peaceful, and centrally located to explore Tuscany. Would definitely recommend!
Top Guest favourite
Cottage in Geggiano
4.99 out of 5 average rating, 129 reviews

Villa di Geggiano – Guesthouse

LauraRating, 5 stars2 weeks ago
The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!
Guest favourite
Cottage in Castell'Azzara
4.98 out of 5 average rating, 133 reviews

Your Private Tuscan Retreat

ShaunRating, 5 stars3 weeks 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.
Top Guest favourite
Home in Simignano
4.97 out of 5 average rating, 115 reviews

Casa al Gianni - The Simignano Barn

RebeccaRating, 5 stars6 days ago
Cristina’s villa was the perfect Tuscan escape for our family. There is much to love…the sweet pigs, the village dogs, the breathtaking views, the peaceful and quiet evenings and mornings, delicious food and beer produced on the farm, AND the most lovely and kind family/hosts. I could honestly go on and on about how much we loved this villa and location. 5 stars all the way! We had our 6 yr old daughter with us and she says it was her favorite place she has stayed on a holiday because of the pigs, ping pong table, swing, and because she had so much fun with the host family children and other guests whom stayed in the other available villas. Also, the big dinner hosted on the last night of our stay was the highlight of our trip! (Tip: make sure to buy some of their products made on the farm….so delicious!)
Guest favourite
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

PeterRating, 5 stars4 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.
Top Guest favourite
Apartment in Pienza
4.9 out of 5 average rating, 162 reviews

Back Home - Apartment in Pienza

MorganRating, 5 stars1 month ago
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!
Superhost
Farm stay in Orbetello
4.65 out of 5 average rating, 116 reviews

Ground floor studio apartment in Farmhouse - pool

VanessaRating, 5 stars1 week ago
Everything was perfect, beautiful, relaxing, super well-stocked and clean! I highly recommend it for enjoying the holidays in total relaxation. Massimiliano is very kind and very helpful 😊
Top Guest favourite
Condo in Cortona
4.98 out of 5 average rating, 130 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

John MarkRating, 5 stars2 months 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
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 vacation. Optimal location for reaching Argentario and at the same time enjoying silence and a fantastic view on the way back. The apartment is very well maintained 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 stars33 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 stars7 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 favourite
Condo in Asciano
4.99 out of 5 average rating, 175 reviews

Pink like the sunset sky

KornRating, 5 stars5 days ago
The four of us wished we could’ve stayed longer! The place was beautiful, spacious, and romantic — it gave us a real Tuscany vibe. We cooked, drank wine, and lived the Dolce Vita style. The host was friendly and even shared their balsamic vinegar with us since we forgot to buy some. The price was very reasonable for what we got — no complaints! We’d love to visit again!

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 stars44 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 favourite
Villa in Siena
4.85 out of 5 average rating, 86 reviews

Enchanting Rose Garden Pool Villa

MarkRating, 5 stars6 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
Villa in Rosignano Marittimo
4.92 out of 5 average rating, 25 reviews

Villa Castiglioncello - access to the private sea

JürgRating, 5 stars6 months ago
House, location: right by the sea, fantastic views, spectacular sunsets, large house with special architecture offers plenty of space and privacy, ideal for a large family. Various garden terrace areas. Everything very well maintained and well equipped. Camilla is a very warm and competent host. We will be happy to come back!
Superhost
Home in Gaiole in Chianti
4.8 out of 5 average rating, 100 reviews

loft in the heart of Tuscan Chianti

CharlotteRating, 5 stars6 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 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!
Guest favourite
Farm stay in Pienza
4.94 out of 5 average rating, 170 reviews

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza

BradRating, 5 stars5 days ago
Sabrina and her family were very accommodating and amazing host! The whole stay was superb In every way and my whole family as well as myself noted it couldn’t have been a better experience. From the amazing home cooked breakfast, to the cleanliness of the house, and the well thought out and led cooking class/dinner we enjoyed every aspect. Sabrina was very welcoming and made you feel like family :) I would highly recommend to anyone looking for a peaceful farm style stay that wants to experience Tuscany.
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 favourite
Home in Orvieto
4.82 out of 5 average rating, 22 reviews

House with private pool, air conditioning

FionaRating, 5 stars9 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 holiday rentals that are family-friendly in Grosseto

  • Total rentals

    40 properties

  • Nightly prices starting at

    $63 AUD before taxes and fees

  • Total number of reviews

    500 reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

Destinations to explore