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Kid-friendly holiday rentals in Asciano

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Asciano family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Panzano
4.98 out of 5 average rating, 441 reviews

Old Farmhouse near Panzano Castle Abbacìo

KayRating, 5 stars4 days ago
Before arriving, Stephano informed me in detail if we would get lost, and he also carried a heavy carrier. A welcoming wine gift warmed our heart on the table. He also gave us detailed instructions on how to get on the bus to Florence and the bus stop. He wanted to tell us anything. In the old farmhouse, everything is prepared like a house for family, not travelers. I took pictures of the fantastic sunset and scenery. When I go back to Seoul and get tired of my daily life, I think I will reminisce about this picture. And thank you for the gifts, Nicoletta.
Guest favourite
Home in Castellina in Chianti
4.98 out of 5 average rating, 111 reviews

StageROOM03 -Chianti Idillic Country living

DanielRating, 5 stars2 weeks ago
We loved the villa. It was private and had an incredible setting. Ivan was very responsive and incredibly helpful in suggesting restaurants and other activities. The only issue we had was finding the unit when we arrived. It was a little confusing at first to find our way to the villa.
Guest favourite
Home in Cortona
4.94 out of 5 average rating, 202 reviews

Casa del Passerino

JonathanRating, 5 stars2 weeks ago
Great flat to explore Cortona! Excellent location and had everything you need
Guest favourite
Home in Cerreto Guidi
4.95 out of 5 average rating, 474 reviews

Casa del Giardino

LoriRating, 5 stars4 weeks ago
My husband and I, plus our French Bulldog, had the pleasure of staying here for just over 3 weeks. Immediately felt like home, and host family had everything to do with that! Highly recommend. stunning views, fabulous location and some of the most gracious people I've ever met.
Top guest favourite
Home in San Quirico d'Orcia
4.99 out of 5 average rating, 208 reviews

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

RobynRating, 5 stars2 days ago
We felt like kings of the castle in Stefano and Sylvias’s place. Top of a hill with expansive views and always such a beautiful breeze. San Quirico was lovely as was Bagno Vignoni at the bottom of our hill. We could see the twinkling lights of Pienza and Montepulciano both of which were an easy drive away. Generosity in the way the villa was presented and our hosts’ welcome, with many wonderful local suggestions. Would highly recommend.
Top guest favourite
Home in Villa a Sesta
4.98 out of 5 average rating, 436 reviews

Raffaella's House in Chianti

AshleyRating, 5 stars1 week ago
Very peaceful and beautiful views from the rooms. Raffaella’s breakfast was very good and much appreciated! She gave amazing local food recommendations that are walkable from her house. She also helped us find parking in the city of Florence!
Top guest favourite
Home in Prato
4.98 out of 5 average rating, 133 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

MelanieRating, 5 stars5 days ago
Ilonka & Rob were wonderful hosts & the house was stellar. We thoroughly enjoyed our stay - it was incredibly quiet & peaceful - away from the hustle & bustle yet close enough to enjoy several surrounding towns & villages as day trips or for evening dinners. Their home is charming, super clean, & stocked with everything we could possibly need. They even shared fresh fruits & vegetables from their personal garden which we incorporated into our meals when we cooked at home. We enjoyed some nice walks through the mountainside which offer beautiful views & solitude. (Thanks to our hosts for recommending!) We hope to be back when it is cooler - but we did enjoy the pool during the hot afternoons. Until then, we are grateful to have found this gem & for the kindness extended to us by Ilonka & Rob. They answered all our questions, provided helpful recommendations, & were generous with their time - available when needed & happy to socialize but always respecting guest privacy.
Top guest favourite
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!

Family-friendly apartment rentals

Guest favourite
Flat in Cortona
4.95 out of 5 average rating, 155 reviews

Casa Le Contesse

준엽Rating, 5 stars3 days ago
Her accommodation is really clean and well maintained. The view of the courtyard, where the Tuscany region can be seen at a glance, was really great. Thank you so much for taking care of us so that we can stay comfortably. Always be happy. Thank you.
Top guest favourite
Flat in Montalcino
4.9 out of 5 average rating, 358 reviews

Panoramic Country Suite Montalcino

AmeliaRating, 5 stars1 month ago
We loved our time here! It was a beautiful property exactly as described. Alessandra has great recommendations and lovely wine. We will be back!
Guest favourite
Flat in Laviano
4.9 out of 5 average rating, 114 reviews

Unique location farmhouse

EneidaRating, 5 stars1 week ago
The views are magical. The place is clean. Great communication by host. Close to many towns but a car is def recommended. The pool was refreshing after a day of exploring. Little playground was a nice addition for those traveling with kids. Olive oil made by owners was divine. We would love to come back.
Guest favourite
Flat in Monteroni d'Arbia
4.96 out of 5 average rating, 248 reviews

"Red Rose" apartment with view of Siena.

MauricioRating, 5 starstoday
The place and the attention Marta offers are excellent. A good place to base yourself to visit Tuscany.
Top guest favourite
Flat in Sinalunga
4.99 out of 5 average rating, 275 reviews

Resort Panoramic view - Free parking

EnricoRating, 5 starstoday
Charming stay, room and patio with a view that is unparalleled in beauty and tranquility. Beautiful room, well-stocked, everything extremely well cared for in detail by a person - Elena, although we did not have the opportunity to meet - who puts love into providing an experience that is absolutely to be repeated. The common areas are also extremely well-kept and comfortable.
Guest favourite
Flat in Castelnuovo Berardenga
4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

RachelRating, 5 stars1 week ago
This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.
Top guest favourite
Flat in La Presura
4.93 out of 5 average rating, 146 reviews

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

AndreaRating, 5 stars2 weeks ago
This was such an amazing stay! Very quiet, peaceful, and relaxing stay far away from the major cities. Beautiful views from everywhere! Would recommend doing their wine tour on site. It was fun, informative, and delicious! You definitely will need a car to get to this place in addition to restaurants and grocery stores. Would highly recommend this place!
Top guest favourite
Flat 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 been to 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 switch off 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!

Family-friendly apartment rentals

Top guest favourite
Apartment in Strada In Chianti
4.95 out of 5 average rating, 372 reviews

Chianti Apartment in 12th Century Tuscan farmhouse

DrewRating, 5 stars1 week ago
I highly recommend Bryan's place it is extremely beautiful and well maintained with an amazing back drop. Bryan and his family are very welcoming. If you want a taste of Tuscany you need to stay here.
Guest favourite
Apartment in San Gimignano
4.93 out of 5 average rating, 118 reviews

Luxury Medieval Tower - Penthouse

RussRating, 5 stars1 month ago
We stayed for 5 night and enjoyed this large, well appointed two story apartment. The place was warm and inviting and was an authentic home to be a unique setting. My family enjoyed the surroundings and there was plenty of restaurants to close from. Be prepared to tackle the 52 steps to the apartment door which my 90 year old mother managed twice a day. Keeps you healthy.
Guest favourite
Apartment in Chiusdino
4.87 out of 5 average rating, 103 reviews

Apartamento Chiusdino - Old Town

NicholasRating, 5 stars1 month ago
Excellent accommodation, house as per photos and description, located in a very nice little village. Clean and tidy structure, Host always available for any information and kind.
Top guest favourite
Apartment in Pienza
5 out of 5 average rating, 111 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

SachinRating, 5 stars2 weeks ago
A beautiful Agro tourismo right in the lap of nature…very close to the picturesque Pienza town and with gorgeous views of Tuscany rolling hills all around the house.. Bianca’s father met us upon arrival and explained us all the details about the house, his farm, olive oil making and the background of the place.. They stay on the first floor of the house and Airbnb is on ground floor… The house was built in 1576 and it was one of its kind of experience to be staying in it… The house is quite spacious and very well decorated. We stayed here for 3 nights and did 2 day trips - 1 to Florence and other to Siena ( a must visit place with marvellous cathedral and piazza del campo ) and picture perfect Chianti region.. Having a car is absolutely necessary as the place is 8-10 km from Pienza and public transport is minimal… Regards, Sachin
Top guest favourite
Apartment in Barberino Tavarnelle
5 out of 5 average rating, 252 reviews

Old medieval apartment

NicolettaRating, 5 stars2 weeks ago
Leonardo was incredible helpful and an absolute delight. You can tell he is house proud, the place was peaceful and beautiful. I would go back.
Top guest favourite
Apartment in Torrenieri
4.97 out of 5 average rating, 241 reviews

[9 minutes from Montalcino] Elegant House Mafalda

AnthonyRating, 5 stars2 weeks ago
Marco’s place is away from the hustle and bustle of Siena very quietly comfortable and super clean. The view from the balcony alone is worth the night rate. Close to all the lovely sights in Val D’Orcia. In a very quaint town with locals who actually live here. Marco is very responsive and clearly explained everything to us. Must try the pizza at Pizza I’ll Vecchio…a hidden gem in Tuscany
Top guest favourite
Apartment in Centro Storico
4.96 out of 5 average rating, 328 reviews

Apartment in Florence, Italy

SimonRating, 5 stars2 days ago
Great stay, everything is in walking distance 5 minutes to busses and trains. Apartment was beautiful loved sitting outside in the courtyard. Eugenia was super helpful and friendly, definitely recommend.
Top guest favourite
Apartment in Siena
4.96 out of 5 average rating, 170 reviews

Elegant vintage decorated home in the old Siena

DeniseRating, 5 stars3 weeks ago
Perfectly located vintage decorated home within walking distance of historic center of Siena. We spent a month here and used her place as a center base to discover Tuscany. Close to shopping and restaurants. WiFi is excellent as my husband worked remotely for a few days a week. Kitchenette and washing machine were a big help as we cooked a few nights staying in. Mattress is very comfy and the apartment is very quiet. Church bells rang daily and drummers in the contrade practice for parades and Palio. Experience Medieval Siena here. We were very comfortable in Grazia’s place. Nice to have a 1/2 bath on main level, as bedroom and bathroom with shower is on the upper level. Grazia provides everything you could possibly want and has excellent suggestions for places to eat and sights to visit. She was indispensable helping us always responding within minutes if we had a question or needed help. Perfect place for the Tuscan vacation! Grazia is a wonderful and caring host!

Quick stats about holiday rentals that are kid-friendly in Asciano

  • Total rentals

    100 properties

  • Nightly prices starting at

    $51 SGD before taxes and fees

  • Total number of reviews

    3.3K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with a pool

    70 properties have a pool

Destinations to explore

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