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Family-friendly holiday rentals in Grosseto

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Grosseto

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Home in Petrignano sul Trasimeno

4.83 out of 5 average rating, 40 reviews

Beautiful family home overlooks Tuscan hills

Our gorgeous family home is on the Tuscany/Umbria borders and has stunning views over the Tuscan hills and village of Montepulciano. Set in a quiet location, amongst olive & fig trees it is perfect for a relaxing family holiday. The house is very spacious with plenty of room inside & out for children to play and adults to unwind. Castiglione and Lake Trasimeno are a 10 minute drive away, with shops, beach, restaurants and children's play areas as well as local ferry access to the lake islands.

Farm stay in Cortona

4.64 out of 5 average rating, 11 reviews

Poggio Martino | Farmhouse with Pool

Villa Poggio Martino is an old independent farmhouse with an area of about 600 square meters, divided into seven independent apartments. Each apartment has a living area, kitchen and one or more bedrooms and bathrooms. A barbecue is available, and there is a beautiful swimming pool in the garden. The panoramic location overlooking the hills of Montepulciano and the surrounding countryside create a serene atmosphere for our guests The Villa has been restored in perfect rural Tuscan style.

Guest favourite

Home in Monte Argentario

4.75 out of 5 average rating, 36 reviews

Beach villa great view, chill space, dogs welcome

Beautiful contemporary beach house, furnished in a warm beach style accommodates up to 8 guests. Fully modernized with heating and cooling. Parking available. - Extra deep cleaning and a day in between our guests :) two independent levels in one villa with over 100m2. On a lovely sandy beach but also on the road so except some noise. Loads of parking. Extra large outdoor living room, hot outdoor shower, hammock, marble dining table & grill to eat alfresco amongst other comforts.

Guest favourite

Villa in Monteriggioni (SI)

4.97 out of 5 average rating, 149 reviews

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

Guest favourite

Home in Bolsena

5 out of 5 average rating, 53 reviews

Bolsena House

This is our vacation home in beautiful Bolsena. We rent it out when we do not use it ourselves. This view is from our rooftop terrace. It overlooks the Santa Cristina Basilica and Bolsena lake - the largest lake of volcanic origin in Europe. Our house is located in the center of the old town, only a few minutes walk from the waterfont with its charming marina, peaceful beaches and numerous good restaurants. Pets are allowed upon request.

Flat in Bucine

4.75 out of 5 average rating, 4 reviews

Lupinari Estate - La Limonaia

Tenuta Lupinari is located in Valdambra, one of the most evocative and uncontaminated places in the Chianti area. Our apartments are the result of a careful restoration of a 16th-century village nestled in the Tuscan hills, strategically located between Arezzo, Siena and Florence. It is an ideal place both to spend the days full of relaxation and to visit the artistic beauty of our land of Tuscany.

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Bungalows

Intimate homes, inviting architecture

Popular amenities for Grosseto family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Pitigliano

4.75 out of 5 average rating, 8 reviews

Sleep in the Castle

Home in Gaiole In Chianti

4.86 out of 5 average rating, 248 reviews

Charming estate with views

Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 123 reviews

Villa di Geggiano - Guesthouse

Guest favourite

Cottage in Castell'azzara

4.98 out of 5 average rating, 128 reviews

Your Private Tuscan Retreat

Guest favourite

Flat in Montepulciano

4.91 out of 5 average rating, 139 reviews

Charming House in Montepulciano

Guest favourite

Home in Simignano

4.96 out of 5 average rating, 102 reviews

Casa al Gianni - Il Fienile di Simignano

Guest favourite

Flat in Asciano

4.84 out of 5 average rating, 121 reviews

Apartment RASPBERRY in Podere di Sant'Antonio

Guest favourite

Apartment in Cortona

4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

Family- and pet-friendly home rentals

Flat in Campo nell'Elba

4.76 out of 5 average rating, 34 reviews

Countryside cottage

Home in Staggia

4.87 out of 5 average rating, 39 reviews

Holiday in the Chianti Senese

Farm stay in orbetello

4.63 out of 5 average rating, 108 reviews

Ground floor studio apartment in Farmhouse - pool

Guest favourite

Apartment in Cortona

4.98 out of 5 average rating, 125 reviews

Casa Clara Cortona and

Guest favourite

Flat in Montiano, Magliano in Toscana

4.98 out of 5 average rating, 44 reviews

Poggio Bestiale holiday home

Apartment in Ponteginori

4.87 out of 5 average rating, 15 reviews

Romantic and cozy two-room apartment

Flat in San Quirico d'Orcia

4.5 out of 5 average rating, 6 reviews

Oleandro real farm house in the Tuscan countryside

Farm stay in Montepulciano

4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

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

Guest favourite

Villa in Città della Pieve

4.88 out of 5 average rating, 16 reviews

Villa Miralaghi heated pool fitness park on a hill

Guest favourite

Villa in Sovicille

5 out of 5 average rating, 12 reviews

TRUE TuscanProperty Exclusive useSiena20P A/C Pool

Guest favourite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

Flat in Siena

4.67 out of 5 average rating, 6 reviews

Splendid house with garden, pool, 5km from Siena

Guest favourite

Farm stay in Pienza

4.93 out of 5 average rating, 169 reviews

Agriturismo Palazzi del Papa Val d 'Orcia Pienza

Home in Piombino

5 out of 5 average rating, 13 reviews

Between the sea and tradition, an anti-stress vacation!!!

Guest favourite

Home in Orvieto

4.82 out of 5 average rating, 22 reviews

House with private pool, air conditioning

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

Total rentals
40 properties
Nightly prices starting at
₹3,397 before taxes and fees
Total number of reviews
560 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Destinations to explore