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Family-friendly holiday rentals in Asciano

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Popular amenities for Asciano family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite

Loft in Reggello

4.89 out of 5 average rating, 131 reviews

CASA AL BOSCO 1

AlejandraRating, 5 stars3 months ago
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!
Guest favourite

Villa in Montepulciano

4.91 out of 5 average rating, 119 reviews

Villa in Montepulciano with Pool

MosesRating, 5 stars3 months ago
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 🥰
Superhost

Home in Gaiole In Chianti

4.86 out of 5 average rating, 249 reviews

Charming estate with views

MoritzRating, 5 stars2 months ago
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.
Guest favourite

Villa in San Casciano in Val di Pesa

4.94 out of 5 average rating, 161 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

RyanRating, 5 stars1 month ago
A lovely home that has clearly been well cared for alongside a beautiful landscape of vineyards and olive groves. Our host was very attentive and available for any questions and we couldn't have had a nicer time.
Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 126 reviews

Villa di Geggiano - Guesthouse

GabrielRating, 5 stars3 weeks ago
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.
Guest favourite

Cottage in Castell'azzara

4.98 out of 5 average rating, 129 reviews

Your Private Tuscan Retreat

IliaRating, 5 stars1 month ago
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.
Guest favourite

Condo in Cortona

4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

PeterRating, 5 stars1 month ago
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
Guest favourite

Apartment in Firenze

4.89 out of 5 average rating, 325 reviews

Apartment with garden and parking

Iveth EstherRating, 5 stars2 months ago
Giuseppe and his wife are very good, friendly and helpful people. His house was in very good condition and had what we needed for our stay. A very nice garden. They gave us a good reception and we had a parking lot for us in the same place. Very grateful to them and we would certainly repeat.

Family- and pet-friendly home rentals

Guest favourite

Guest suite in Centro Storico

4.95 out of 5 average rating, 165 reviews

A stone's throw from downtown and away from the chaos

KerrieRating, 5 stars2 months ago
Had such a perfect stay here. Slightly out of Florence town but great if you enjoy a small post food walk to work off all the delicious food on offer. Really peaceful. Stefani gave some lovely recommendations. Perfect host, perfect place. Happily stay again.
Guest favourite

Condo in Cortona

4.98 out of 5 average rating, 128 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

MassimilianoRating, 5 stars1 month ago
Clara's apartment is perfect for visiting Cortona. Downtown, close to several typical restaurants. Very clean and well furnished, there was everything you need. Thank you Clara for your availability and kindness. I recommend it to anyone who wants to stay in Cortona.
Superhost

Apartment in Volterra

5 out of 5 average rating, 4 reviews

APARTMENTS 3 people+ 4 people

KasiaRating, 5 stars30 months ago
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!
Superhost

Home in Gaiole in Chianti

4.8 out of 5 average rating, 100 reviews

loft in the heart of Tuscan Chianti

CharlotteRating, 5 stars3 months ago
We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.
Guest favourite

Home in Subbiano

4.99 out of 5 average rating, 78 reviews

Romantic cosy flat - Toscana Italy

DavidRating, 5 stars3 months ago
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
Superhost

Farm stay in Montepulciano

4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

SylvanaRating, 5 stars4 months ago
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:-)
Guest favourite

Condo in Asciano

5 out of 5 average rating, 162 reviews

Pink as the sunset sky

하늘Rating, 5 stars2 months ago
Famous small towns around Tuscany are expensive, but this is a place where you can fully enjoy the natural scenery of Tuscany at a reasonable price. The host was very friendly and the house was a very nice place to get a hands on experience of the farmhouse. It's an old brick house, but the antique interior and natural scenery were great.
Guest favourite

Apartment in Caminino

4.91 out of 5 average rating, 160 reviews

Pieve di Caminino Historic Farm

PearlsRating, 5 stars2 months ago
I have been traveling around Italy for all summer and autumn, I must say that Emiliano's place was the best stay by far I have visited. I felt like home through my entire stay. Emiliano and his family made me feel very welcomed and invited me to join them at the dinner table, what an absolute ultimate Tuscany experience that was! I couldnt have wished for a better way to wrap up my stay in Italy. Emiliano knows very well the area and can recommend lots of wineries to visit and restaurants to dine at. But the olive farm is so breathtaking and peaceful that you may not feel like going away, the place has everything you need if you are looking to escape from a busy city life style. Accomodation is very charming and one weekend was not enough, Wish I could stay longer.

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

MarkRating, 5 stars4 months ago
We booked Villa Montechiarone as part of our wedding at Montechiaro Organic Winery to house a group of 7 guests. The property sits around 500m from the winery itself, with views out over the Tuscan countryside, it's a breathtaking location and the villa itself is an incredible space. There are 2 huge indoor living areas, a well equipped kitchen, 4 spacious bedrooms and an outdoor covered terrace, as well as the garden and pool area. There is real character in the property in the way it is decorated as well as the imposing facade of the building itself. The pool area is spacious and well placed to take in the most of the view, and there is a car port with parking for at least 4 cars covered, with plenty more room if required beyond. Overall perfect for housing our guests who had a great experience and were very thankful for the help whilst checking out also!
Guest favourite

Apartment in Gaiole In Chianti

4.76 out of 5 average rating, 21 reviews

Idyllic with shared pool in the heart of Chianti

GuidoRating, 5 stars5 months ago
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!
Guest favourite

Villa in Ortignano Raggiolo

4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars3 months ago
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!
Superhost

Apartment in Montespertoli

4.89 out of 5 average rating, 9 reviews

12/14 pers,WiFi,Sw-pool,catering

MartinaRating, 5 stars22 months ago
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!!
Guest favourite

Home in Lecchi in Chianti

4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars3 months ago
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!
Superhost

Villa in Talla

4.91 out of 5 average rating, 23 reviews

Lovely villa heated outdoor pool & tennis court

LoriRating, 5 stars3 months ago
The villa exceeded our expectations. It was exceptionally clean and well cared for. Excellent amenities. Beautiful surroundings with olive and lemon trees. Cute little village nearby with an excellent restaurant. The host was very responsive. We had a bit of trouble finding the place but that might be more us than the directions. You definitely need a rental car Thank you for an amazing stay
Guest favourite

Apartment in La Felce

4.98 out of 5 average rating, 107 reviews

La Felce Country House

GarrettRating, 5 stars4 months ago
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!
Guest favourite

Farm stay in Pienza

4.93 out of 5 average rating, 169 reviews

Agriturismo Palazzi del Papa Val d 'Orcia Pienza

LeslieRating, 5 stars2 months ago
Nice agriturismo, very chill place and beautiful surroundings

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

  • Total rentals

    450 properties

  • Nightly prices starting at

    $48 AUD before taxes and fees

  • Total number of reviews

    6.9K reviews

  • Pet-friendly rentals

    230 properties allow pets

  • Rentals with a pool

    330 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