Family-friendly holiday rentals in Province of Siena
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Province of Siena
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Province of Siena family-friendly rentals
Family-friendly home rentals with a hot tub
Cottage in Radicondoli
4.95 out of 5 average rating, 110 reviewsBeautiful renovated barn in Tuscany
26 Sept – 3 Oct
Villa in Castiglion Fiorentino
4.93 out of 5 average rating, 181 reviewsTuscan charm of villa - countryside
10–17 Mar
Home in Gaiole In Chianti
4.85 out of 5 average rating, 222 reviewsCharming estate with views
12–19 Dec
Farm stay in Gaiole in Chianti
4.94 out of 5 average rating, 201 reviewsIl Piccolo Nido alla Pieve Marsina
15–22 Aug
Apartment in Chiusi
4.95 out of 5 average rating, 130 reviewsLa Terrazza su Chiusi - panoramic apartment
7–14 Nov
Flat in Montepulciano
4.91 out of 5 average rating, 122 reviewsCharming House in Montepulciano
12–19 Dec
Apartment in Casole d'Elsa
4.93 out of 5 average rating, 124 reviewsLa Casetta
27 Dec – 3 Jan
Apartment in Montevarchi
4.94 out of 5 average rating, 176 reviewsArt-Design Fienile in the heart of Tuscany
6–13 Jul
Family- and pet-friendly home rentals
Guest suite in Greve in Chianti
4.94 out of 5 average rating, 381 reviewsSelvabella in Chianti B&B. Suite Lo Scricciolo
13–18 Oct
Loft in Siena
4.91 out of 5 average rating, 322 reviewsHoliday Apartment Stilnuovo, Siena center
16–23 Nov
Flat in Siena
4.8 out of 5 average rating, 234 reviewsNonna Rina House
20–27 Jul
Apartment in Asciano
4.96 out of 5 average rating, 245 reviewsYellow Romantic apartment in the Sienese crete
7–14 Dec
Flat in Caminino
4.92 out of 5 average rating, 130 reviewsPieve di Caminino Historic Farm
8–15 Dec
Villa in Ambra
4.98 out of 5 average rating, 108 reviewsChianti Villa in Tuscany near Siena & Arezzo
18–25 Dec
Home in Siena
4.79 out of 5 average rating, 743 reviewsLittle heaven on the hills
4–11 Jan
Home in Scrofiano
4.97 out of 5 average rating, 116 reviewsJenny's Barn
1–8 Oct
Family-friendly home rentals with a pool
Villa in Castellina in Chianti
4.93 out of 5 average rating, 166 reviewsThe Villino Farmhouse
3–10 Apr
Flat in Laviano
4.95 out of 5 average rating, 100 reviewsFarmhouse with swimming pool with wonderful view
30 Dec – 6 Jan
Flat in San Gimignano
4.89 out of 5 average rating, 134 reviewsApartment Melogranowith great views
20–27 Nov
Farm stay in Murlo
4.99 out of 5 average rating, 136 reviewsCountry house near Siena
1–8 Nov
Farm stay in Castelnuovo dei Sabbioni
4.92 out of 5 average rating, 302 reviewsChianti La Pruneta, Raffaello Apartment
24–31 Oct
Farm stay in Montepulciano
4.96 out of 5 average rating, 137 reviewsSeparate room, between Cortona and Montepulciano
27 Feb – 6 Mar
Home in Rietine
4.85 out of 5 average rating, 186 reviewsGaiole in Chianti Poggio Casabianca
28 Apr – 5 May
Apartment in arezzo
4.97 out of 5 average rating, 198 reviewsExplore Nature in Downtown Chianti Vigneti
30 Dec – 6 Jan
Destinations to explore
- Family-friendly rentals Italy
- Family-friendly rentals Florence
- Family-friendly rentals Tuscany
- Family-friendly rentals Tuscany
- Family-friendly rentals Bologna
- Rentals with a fireplace Province of Siena
- House rentals Province of Siena
- Rentals with an EV charger Province of Siena
- Flat rentals Province of Siena
- Loft rentals Province of Siena
- Rentals with a sauna Province of Siena
- Rentals with an accessible-height bed Province of Siena
- Rentals with a hot tub Province of Siena
- Cottage rentals Province of Siena
- Private suite rentals Province of Siena
- Smoking-friendly rentals Province of Siena
- Tiny house rentals Province of Siena
- Rentals with pools Province of Siena
- Ski-in/ski-out rentals Province of Siena
- Rentals with a balcony Province of Siena
- Boutique hotel rentals Province of Siena
- Family-friendly rentals Province of Siena
- Holiday home rentals Province of Siena
- Rentals with a firepit Province of Siena
- Guest house rentals Province of Siena
- Monthly Rentals Province of Siena
- Rentals with a patio Province of Siena
- Rentals with lake access Province of Siena
- Barn rentals Province of Siena
- Fitness-friendly rentals Province of Siena
- Villa rentals Province of Siena
- Wheelchair-accessible rentals Province of Siena
- Rentals with outdoor seating Province of Siena
- Hotel rentals Province of Siena
- Farm stay rentals Province of Siena
- Tent rentals Province of Siena
- Bed and breakfasts Province of Siena
- Serviced apartment rentals Province of Siena
- Apartment rentals Province of Siena
- Luxury rentals Province of Siena
- Castle rentals Province of Siena
- Rentals with a washing machine and dryer Province of Siena
- Pet-friendly rentals Province of Siena
- Nature eco lodge rentals Province of Siena
- Rentals with breakfast Province of Siena
- Townhouse rentals Province of Siena
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom