
Family-friendly holiday rentals in Asciano
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Asciano
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 Asciano family-friendly rentals
Family-friendly home rentals with a hot tub

CASA AL BOSCO 1
We had a very pleasant time here. Carlotta was very friendly from the start, and even recommended local grocery stores. This place is a hidden gem! You are surrounded by beautiful trees & nature, but close enough to the town where you can easily catch the train to Florence. We absolutely loved it!

Villa in Montepulciano with a Pool
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 🥰

Charming estate with views
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.

The Vichiaccio Villa with Jacuzzi in Chianti
Incredible stay at Beatrice’s place. From booking to exit she had helped my group and I plan our stay in Tuscany finding wineries and vineyards to explore. She was so kind and pleasant to work with I would suggest her place to anyone! The kitchen was cozy and perfect for our group to spend time in while at the bnb. Every room was exactly as described. Perfect stay!

Villa di Geggiano - Guesthouse
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.

Your Private Tuscan Retreat
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.

Tuscany Seen in a Fabulouse House
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

Casa Purgatorio, a typical property in Tuscany
We had a wonderful stay at Laura's beautiful property. The surroundings are spectacular. The property has a lovely pool and terrace with BBQ and large table, perfect for eating, drinking and looking out at the beautiful views. We stayed in the one bedroom property which was perfect for my wife and I. The bedroom, kitchen, bathroom and living area where well laid out and the decoration was clean and well though out. Laura met us on arrival and provided some fantastic recommendations for local restaurants. Would very much hope we go back some time.
Family- and pet-friendly home rentals

La Maison di Monica & Simona
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.

A stone's throw from downtown and away from the chaos
Matrace is of memory foam. I slept very well but just something you should know if you don‘t like this type of matrace. Extra blankets were there and overall super comfortable bed. Wifi speed was fine, not as fast as I would have liked. Host was really nice. We would definitely come back here! Use the app „easypark“ for nearby affordable parking on a „pay as you go“ basis. Shop im the nearby esselunga supermarket.

Casa Clara Cortona Cin IT051017c28a6h9glv
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!

APARTMENTS 3 people+ 4 people
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!

Romantic cosy flat - Toscana Italy
This was exactly what we were looking for. Very peaceful and private with beautiful views. Lots of wonderful villages to visit and explore within a 30 minute drive. Norma made some great reservations for our anniversary dinner as well as a couple of great wine tours. She also gave us recommendations of which villages were best to visit and what to do there. We highly recommend doing the cooking lessons with her family. They are such a nice family and were very eager to show us how to cook a traditional Tuscan meal. Grandma really is an amazing cook. They even sat with us as a family to share what we had cooked. We have been to many AirBnB’s and Norma has been our best host by far. We would go back the next time we visit Tuscany. Dave and Liz

La Manonera Farmhouse "La Casa Rosa for families"
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:-)

Pink as the sunset sky
very beautiful house, safe and clean. senary is very speic. close to famous sightseeing.

Pieve di Caminino Historic Farm
the structure is a dream... we stayed in Foresteria, better than the photos!!! Perfect place for those looking for tranquility with respect and in full contact with nature. Emiliano wonderful host, he made us find the fireplace on, he allowed us to bring our dogs and leave them free in his beautiful estate and gave us many tips on activities to do nearby... we can't wait to come back!!
Family-friendly home rentals with a pool

Medieval Cottage near Cortona
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!!

Tuscan Villa with Privacy,Pool,near towncentre
We had a quick 36 hour stop here during our honeymoon trek though Italy and Sara’s place was a great place to reset and relax for a bit. We loved visiting Volterra (relatively tourist free compared to our other stops) and the guest villa we stayed in was very cozy and comfortable. Sara and her husband were very helpful with anything we needed and they even left us a bottle of champagne on our last night!

Idyllic with shared pool in the heart of Chianti
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!

Private Villa with swimming pool in Tuscany
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

12/14 people, WiFi, SW pool, catering
The place is magnificent and very well kept, clean and super cozy. It's a little out of the way but we chose it just for the secluded location and surrounded by nature; in any case with a halfhour by car you can get to several wonderful places. Nicola was very kind and helpful. I highly recommend a stay here, it's refreshing!!

Restored Farmhouse & Cottage with AC, Pool & WIFI
For our family vacation, three couples and a 1-year old, the place was perfect. The ability to spend the heat of the day in the huge pool or inside the refreshing lodging made the stay excellent. The place is close to groceries, pharmaceuticals, restaurants, local sites, cities, etc. Ken was always responsive to whatever issue we brought up and his quick replies were greatly appreciated.

Casa di Lyndall - Entire house with exclusive pool
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!

La Felce Country House
Cristina is the ultimate host! Everything was immaculate and set up for us. We traveled with two young kids, and she was proactively prepared with a crib & high chair. She also had amazing recommendations and answered any questions for us. Led us to a spectacular sunset winery in the hills. The premise has stunning views and hanging poolside in the mountains, was just what the doctor ordered. Highly recommended and makes you feel like family!
Quick stats about holiday rentals that are family-friendly in Asciano
Total rentals
410 properties
Nightly prices starting at
$64 AUD before taxes and fees
Total number of reviews
6.8K reviews
Pet-friendly rentals
210 properties allow pets
Rentals with a pool
310 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Destinations to explore
- Florence Holiday rentals
- Pisa Holiday rentals
- Rimini Holiday rentals
- Bologna Holiday rentals
- Rome Holiday rentals
- Cinque Terre Holiday rentals
- Portofino Holiday rentals
- Riviera di Levante Holiday rentals
- Francavilla al Mare Holiday rentals
- Genoa Holiday rentals
- Verona Holiday rentals
- Italian Riviera Holiday rentals
- Family-friendly rentals Italy
- Family-friendly rentals Apennine Mountains
- Family-friendly rentals Tuscany
- Family-friendly rentals Florence
- Family-friendly rentals Province of Siena
- Bed and breakfasts Asciano
- Rentals with breakfast Asciano
- Fitness-friendly rentals Asciano
- Farmstay rentals Asciano
- Condo rentals Asciano
- Rentals with outdoor seating Asciano
- Rentals with a fire pit Asciano
- Rentals with pools Asciano
- Rentals with an EV charger Asciano
- Rentals with a patio Asciano
- Smoking-friendly rentals Asciano
- Holiday home rentals Asciano
- Kid-friendly rentals Asciano
- Rentals with a washing machine and dryer Asciano
- Apartment rentals Asciano
- Rentals with lake access Asciano
- Monthly Rentals Asciano
- Rentals with a hot tub Asciano
- Luxury rentals Asciano
- House rentals Asciano
- Pet-friendly rentals Asciano
- Villa rentals Asciano
- Rentals with a fireplace Asciano
- 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