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Family-friendly vacation rentals in Asciano

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Asciano family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Farm stay in Figline e Incisa Valdarno
4.92 out of 5 average rating, 325 reviews

Bioagriturismo colline Firenze 3p

JayRating, 5 stars3 days ago
Our stay was a dream to be in. Francesca and Francesco have created a wonderful place, are likeable people and great hosts. We were warmly welcomed and received all the necessary information. From the first moment, we felt at home and could freely explore the lovingly designed grounds and also enjoy them in privacy. The contact with other guests was also pleasant and respectful. The rooms are rustic and tastefully decorated and exude a special charm. The view will take your breath away. The approach to Poderracio is correspondingly adventurous (hairpin bends and narrow, bumpy road). All products such as the breakfast basket are super delicious and of high quality. In addition, we received freshly harvested vegetables (zucchini, beets, onions and garlic) from Francesca. During the stay, we were invited to bake pizza together in the private rooms and enjoyed a wonderful evening. THANKS!
Top guest favorite
Cottage in San Casciano In Val di Pesa
4.95 out of 5 average rating, 147 reviews

Il Fienile, Cottage in the country with Jacuzzi

BethanyRating, 5 stars3 weeks ago
If I could move in here permanently, I would. What a gorgeous stay with responsive and respectful hosts. Everything was as described, the hot tub was glorious, and we loved looking through the binder of photos of painstaking restoration over the years.
Guest favorite
Condo in Montevarchi
4.95 out of 5 average rating, 192 reviews

Art-Design Fienile in the heart of Tuscany

AlisterRating, 5 stars2 weeks ago
Incredible trip. Paola and Michele were so friendly and welcoming. Always there to give advice and make sure you had everything you needed. The little converted hay barn was just beautiful and lovely. Location wise it just couldn’t be beaten. The garden was amazing and we ate outside morning and night, easy access to amazing Tuscany countryside and also a short trip on the train to Florence from Montevarchi. Loved every minute we were there and we were sorry to leave. Would highly recommend.
Top guest favorite
Home in Figline e Incisa Valdarno
4.96 out of 5 average rating, 105 reviews

Torretta Apartment

DebbieRating, 5 stars1 week ago
I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!
Guest favorite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars1 week ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Guest favorite
Condo in Casole d'Elsa
4.93 out of 5 average rating, 157 reviews

La Casetta

RalfRating, 5 stars3 weeks ago
We can absolutely recommend it! Everything is as described in the text and seen in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information about the arrival and many great local tips, always with the corresponding links. For example, our arrival was delayed due to traffic to about 10:15 pm. Was no problem, we were in contact and when we arrived, Andrea personally welcomed us. And if we had a question during our stay, an answer always came very quickly. (Where to park in Siena, how to get to Florence, ...)
Guest favorite
Apartment in Florence
4.89 out of 5 average rating, 339 reviews

Apartment with garden and parking

ClaudeRating, 5 stars2 weeks ago
Our hosts welcomed us with great kindness and gave us all the information to direct us to Florence. The very cute and fresh apartment has a very nice flowery and peaceful garden. We had a great time
Guest favorite
Villa in Chianciano Terme
4.92 out of 5 average rating, 107 reviews

Cottage in Val d'Orcia, Jacuzzi & HotTub with view

MadisonRating, 5 stars1 week ago
Fulvia’s apartment is a true Tuscan gem—beautifully decorated with charm and character, and equipped with everything you need. The property offers stunning views and a peaceful sense of seclusion, and it’s even more beautiful than in the photos. Fulvia is right nearby and always available if you need anything. She and her husband are both warm, thoughtful, and made us feel genuinely welcome. Fulvia even arranged dinner at a local restaurant, which turned out to be one of the best meals of our trip. This is a special place and our only regret is not staying longer.

Family- and pet-friendly home rentals

Top guest favorite
Castle in Montecatini Val di Cecina
4.99 out of 5 average rating, 118 reviews

Belforti Tower

JoyRating, 5 stars2 days ago
What a wonderful week we had with Luca and Emilia at the tower! It was amazing to see all the pictures in real life - it was even more amazing in person. And the garden is just magical. I had no idea the beauty of the pool area. Laying by the pool and listening to nature we felt transported to a simpler time. To top it off Luca was so delightful. We enjoyed his company and hearing more about the story of the tower and the town. I would recommend this as a stop on anyone’s vacation to Italy. Wonderful hosts in a magical setting!
Top guest favorite
Villa in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 148 reviews

GUIDI POWER

TerryRating, 5 stars1 week ago
Giuliani is a wonderful host who made us feel as if this slice of paradise was our home, too. The location, the meticulously restored home, the views all make for the ultimate Tuscan experience. But Giuliani and her husband bring it all together with their warmth and attentiveness. It was a tough place to say goodbye to — for now. If you are looking for a Tuscan experience, this is it. And remember to ask for the hosts’ home-cooked meal. It is a culinary experience in the very best sense.
Superhost
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars1 week ago
We immediately fell in love with this property. Everything here makes up the image that can be made of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!
Top guest favorite
Apartment in La Presura
4.93 out of 5 average rating, 147 reviews

Country house 9 km to Florence-2+1g,free parking

TimRating, 5 stars1 week ago
Very nice quiet place to stay with Tuscan flair. Great complex also with a pool and a view. Quickly in Florence and on the streets to the excursion destinations. Definitely recommend! We'll be back. :)
Superhost
Farm stay in Roccatederighi
4.92 out of 5 average rating, 136 reviews

Holiday in antique farm, Belvedere

MauriceRating, 5 stars2 weeks ago
What tranquility and what a view. Beautiful estate and super friendly people who try to delight you. Also a nice and nice swimming pool for when it is very hot.
Superhost
Farm stay in Provincia di Siena
4.87 out of 5 average rating, 117 reviews

Spigo - Indipendent Cottage Zampugna

FilipRating, 5 stars4 days ago
Beautiful place, everything ready with refreshments, accommodation quiet and clean ... Air conditioning functional, but almost not needed, because it was a beautiful classic Tuscan accommodation, where we definitely were not the last
Superhost
Farm stay in Castiglione d'Orcia
4.89 out of 5 average rating, 229 reviews

il poderuccio farmhouse studio apartment

RachelRating, 5 stars2 weeks ago
Great stay! Initially the place was a bit further out of town than we had anticipated but we still found it very accessible to lots of the things we hoped to do! The view was amazing! So peaceful to sit on the terrace!
Guest favorite
Castle in Barberino Tavarnelle
4.87 out of 5 average rating, 111 reviews

Suite in Castle of Valle

KapoRating, 5 stars3 weeks ago
We come from Hong Kong, and a building like this is not often seen there. We are very happy to have had the chance to stay at the house. Some of the details in the house really impressed us, especially the antique furniture! Pietro is a great host—very friendly and responsive. I had some pleasant conversations with him. Thanks again!

Family-friendly home rentals with a pool

Guest favorite
Apartment in Castiglione del Lago
4.91 out of 5 average rating, 143 reviews

Ulivo - Charming apartment in the countryside

CharlotteRating, 5 stars1 week ago
Wow, what a beautiful apartment this was. Nestled in the countryside by the Tuscany/Umbria border is this gorgeous farmhouse owned by Simona and Yens and what a find it was! The rolling hills are captivating and if you want to switch off, enjoy visiting beautiful villages, eat lovely food and really rest, this is the place to do it. We were welcomed by their two friendly dogs and received lots of tips about the local area from Yens on arrival. The apartment is spacious and serene. From spending evenings on the patio eating al fresco, watching the stars or having morning swims, we had a wonderful time and would wholeheartedly recommend this to anyone and everyone seeking some peace and quiet. The farmhouse is remote but it's very easy to get anywhere by car and the drives are never dull with the countryside views. It's hard to put into words how relaxing this place is and so I suggest you book and find out, you won't regret it! Thank you so much Simona and Yens!
Top guest favorite
Apartment in Castellina in Chianti
4.97 out of 5 average rating, 113 reviews

Visit Chianti, Siena, S.Gimignano, Florence

CarlyRating, 5 stars1 month ago
The perfect place to explore Chianti each day. We stayed 5 nights and it was just perfect. Great amenities, beautiful pool, bbqs and lovely areas to sit and enjoy the views and the sunset. Always fabulous to come home to. Our upstairs apartment was spacious, comfortable and all we required with a lovely view. We had great recommendations from Silvia which we followed up on. Great to have restaurants nearby. Reasonable- highly recommend.
Guest favorite
Vacation home in Sovicille
4.93 out of 5 average rating, 107 reviews

Podere La Castellina - No. 2 LECCETO

SophieRating, 5 stars2 weeks ago
We had a great stay! Simona welcomed us warmly and showed us everything in peace. The Airbnb is beautifully located in the middle of nature – perfect for unwinding and relaxing. The place was very clean, lovingly and cozily. We felt completely comfortable and would come back anytime. Thank you for the wonderful time!
Guest favorite
Apartment in Carpineto
4.95 out of 5 average rating, 171 reviews

Tuscan countryside, peace and relaxation 10 minutes from Siena

NoahRating, 5 stars1 week ago
Beautiful place near Siena. The hosts are very friendly and kind. We really enjoyed our stay in here!
Top guest favorite
Apartment in Barberino Val d'Elsa
4.99 out of 5 average rating, 122 reviews

Apartment in Chianti at Mulino dell 'Argenna

MarkusRating, 5 stars1 week ago
We have now stayed in Elisa and Alessandro's accommodation for the second time – and it was simply beautiful and absolutely relaxing again! The place is a real oasis where you can unwind perfectly. Elisa and Alessandro are extremely helpful and warm. They provided us with great tips for activities and restaurants, so we could enjoy our stay all around. We'd love to come back and highly recommend this place!
Top guest favorite
Villa in San Leolino
4.99 out of 5 average rating, 110 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

TjadeRating, 5 stars2 days ago
We had a wonderful time in this beautiful house – everything was very clean, lovingly decorated and well equipped. Even with our dog, we felt completely comfortable, it was absolutely dog-friendly! The hosts were incredibly warm and helpful – they immediately felt welcome. A special highlight was the pizza evening offered – it was not only super cozy, but also a real culinary experience. Honestly, one of the best pizzas I've ever eaten! We'd love to come back – absolute recommendation! 🌟
Guest favorite
Farm stay in Gaiole in Chianti
4.95 out of 5 average rating, 103 reviews

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2

GuillaumeRating, 5 stars3 weeks ago
As soon as we arrived, we felt like family, Paula and the team hosted us very well and the accommodation was very comfortable. Our stay was very pleasant, Arianne introduced us to the vineyard and the wines of Le Miccine in a very friendly way. I highly recommend going there for an unforgettable experience in Tuscany in the Chianti Classico region!
Guest favorite
Villa in Siena
4.89 out of 5 average rating, 286 reviews

Villa Capanna, Private Pool, Breathtaking Views

DianaRating, 5 stars3 weeks ago
We had a fabulous stay at the Villa. Laura was so responsive and handled all our needs. She pre booked all our events and was there to greet us when we arrived. We loved the views and kids enjoyed the pool. The wine tasting on property is a must and we thoroughly enjoyed the dinner they prepared for us at the villa. I highly recommend this beautiful spot. Sitting in the patio overlooking the Tuscan countryside was one of the highlights of our vacation. Thanks to Alessandro and his team. We hope to visit again someday!

Quick stats about vacation rentals that are family-friendly in Asciano

  • Total rentals

    430 properties

  • Nightly prices starting at

    G$8,368 GYD before taxes and fees

  • Total number of reviews

    6.6K reviews

  • Pet-friendly rentals

    220 properties allow pets

  • Rentals with a pool

    320 properties have a pool

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

Destinations to explore

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