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Family-friendly holiday rentals in Grosseto

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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 stars3 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 favourite

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 stars6 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, 144 reviews

Relax in the countryside near the sea( Lavanda )

PaulRating, 5 stars3 months ago
Very nice location and host 😊
Guest favourite

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 stars2 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 favourite

Cottage in Geggiano

4.99 out of 5 average rating, 126 reviews

Villa di Geggiano - Guesthouse

GabrielRating, 5 stars3 weeks 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, 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 favourite

Home in Simignano

4.96 out of 5 average rating, 108 reviews

Casa al Gianni - Il Fienile di Simignano

LaraRating, 5 stars3 days ago
We stayed here with a family of 6 with 4 small children and a big dog. The property is as pictured and described if not better. The village is extremely special and quaint .. for me, it is the best place for a true holiday and where the kids are fully entertained. The farm and tour of the village were a bonus and our host Fabio was available for all our needs and extremely polite. I all around could not recommend this place more and they are even renovating and building what should become an exceptional restaurant. We can’t wait to come back, Grazie Milli and ciao !

Family- and pet-friendly home rentals

Superhost

Farm stay in orbetello

4.64 out of 5 average rating, 110 reviews

Ground floor studio apartment in Farmhouse - pool

MikeRating, 5 stars1 month ago
Great value for money, kind host, beautiful natural location.
Superhost

Holiday home in Porto santo Stefano

4.83 out of 5 average rating, 35 reviews

Villino Mare in the sun

BrigitteRating, 5 stars6 months ago
We had a wonderful week at Ale's cottage, with direct sea views and 2 islands. Ale sent a very accurate description of how to find her, incl. Photos of the main branches. It was easy for us to find. We were there with an SUV and 2 e-bikes, so we could easily reach the parking lot to our chalet, also down the slightly steeper road to the chalet. For all vehicles that do not have a higher wheelbase, there is a parking space above Ales house, you are downstairs in 3 -4 minutes walk. Ale gave us a warm welcome, and provided us with tips for restaurants and beaches in the vicinity. Our chalet had everything, there were two of us. 2 terraces, one with outdoor kitchen, in the bedroom there is air conditioning, which we used to fall asleep. We enjoyed the view over the sea to the islands from morning to evening, there was always something to see. We had a great time, thanks Ale!
Guest favourite

Condo in Cortona

4.98 out of 5 average rating, 128 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

MassimilianoRating, 5 stars1 month ago
Clara's apartment is perfect for visiting Cortona. Downtown, close to several typical restaurants. Very clean and well furnished, there was everything you need. Thank you Clara for your availability and kindness. I recommend it to anyone who wants to stay in Cortona.
Guest favourite

Apartment in Montiano, Magliano in Toscana

4.98 out of 5 average rating, 44 reviews

Poggio Bestiale holiday home

ChiaraRating, 5 stars5 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

Condo in Laterina

5 out of 5 average rating, 3 reviews

Casa vacanze Le Fornaci - Apartamento Dondo

ManuelaRating, 5 stars2 months ago
We've been guests to six people. When we arrived in the evening, the apartment was as described, well heated and comfortable The staff is courteous, kind and always available. We had dinner in their restaurant, high quality cuisine at affordable prices. Repeat experience
Superhost

Farm stay in Montepulciano

4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

SylvanaRating, 5 stars4 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 favourite

Condo in Asciano

5 out of 5 average rating, 162 reviews

Pink as the sunset sky

하늘Rating, 5 stars2 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.
Guest favourite

Apartment in Caminino

4.91 out of 5 average rating, 160 reviews

Pieve di Caminino Historic Farm

PearlsRating, 5 stars2 months ago
I have been traveling around Italy for all summer and autumn, I must say that Emiliano's place was the best stay by far I have visited. I felt like home through my entire stay. Emiliano and his family made me feel very welcomed and invited me to join them at the dinner table, what an absolute ultimate Tuscany experience that was! I couldnt have wished for a better way to wrap up my stay in Italy. Emiliano knows very well the area and can recommend lots of wineries to visit and restaurants to dine at. But the olive farm is so breathtaking and peaceful that you may not feel like going away, the place has everything you need if you are looking to escape from a busy city life style. Accomodation is very charming and one weekend was not enough, Wish I could stay longer.

Family-friendly home rentals with a pool

Guest favourite

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 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 stars5 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 in the heart of Tuscan Chianti

CharlotteRating, 5 stars3 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 stars3 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

LeslieRating, 5 stars2 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 favourite

Home in Orvieto

4.82 out of 5 average rating, 22 reviews

House with private pool, air conditioning

FionaRating, 5 stars6 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.
Guest favourite

Guesthouse in Antria

4.92 out of 5 average rating, 126 reviews

A charming Tuscan retreat

EricRating, 5 stars3 months ago
Gorgeous stay! Views were stunning and the villa exceeded expectations. This was a perfect place to unwind and relax. Highly recommend.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    $48 AUD 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

  • Wi-Fi availability

    20 properties include access to Wi-Fi

Destinations to explore

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