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Family-friendly vacation rentals in Castellina in Chianti

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Castellina in Chianti family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Monsummano Terme
4.98 out of 5 average rating, 106 reviews

Holiday House "The Seasons of Bacchus"

KanchayaRating, 5 stars4 months ago
The house is so nice, clean and cozy. Daniele gives us many helpful tips and place to go, very nice and proactive host.We enjoy our stay very much thanks to Daniele. The place is peaceful and easy to go anywhere, Pisa, Lucca, Florence and Cinque terra. Such a lovely house , highly recommend for family tripšŸ‘šŸ¼
Guest favourite
Loft in Reggello
4.89 out of 5 average rating, 131 reviews

CASA AL BOSCO 1

AlejandraRating, 5 stars5 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 a Pool

MosesRating, 5 stars4 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! Itā€™s spectacular. Iā€™ll definitely come back! Hope the price is reasonable the next time šŸ„°
Superhost
Home in Gaiole In Chianti
4.86 out of 5 average rating, 250 reviews

Charming estate with views

MoritzRating, 5 stars3 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, 163 reviews

The Vichiaccio Villa with Jacuzzi in Chianti

AmandaRating, 5 stars1 month ago
Incredible stay at Beatriceā€™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!
Top guest favourite
Home in Piano di Coreglia
4.99 out of 5 average rating, 76 reviews

House of the Sun

ChristianRating, 5 stars5 months ago
We had a lovely stay at Carlo and Elena's. The fenced garden and pool were a real plus. Not to mention all the little touches Carlo was able to have for us, and even a gift for our little puppy. The place is peaceful surrounded by mountains with beautiful views. We would recommend this house and its host because everything was perfect!
Top guest favourite
Cottage in Geggiano
4.99 out of 5 average rating, 126 reviews

Villa di Geggiano ā€“ Guesthouse

GabrielRating, 5 stars2 months 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 AndreaĀ“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
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

PeterRating, 5 stars3 months 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

Family- and pet-friendly home rentals

Superhost
Apartment in Sasso Pisano
4.78 out of 5 average rating, 187 reviews

La Maison di Monica & Simona

MaximeRating, 5 stars2 months ago
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.
Guest favourite
Guest suite in Centro Storico
4.95 out of 5 average rating, 166 reviews

Within walking distance of the center and away from the chaos

ValentinRating, 5 stars1 week ago
Matrace is of memory foam. I slept very well but just something you should know if you donā€˜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 ā€žeasyparkā€œ for nearby affordable parking on a ā€žpay as you goā€œ basis. Shop im the nearby esselunga supermarket.
Top guest favourite
Condo in Cortona
4.98 out of 5 average rating, 129 reviews

Casa Clara Cortona Cin IT051017c28a6h9glv

John MarkRating, 5 stars1 month ago
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!
Superhost
Apartment in Volterra
5 out of 5 average rating, 4 reviews

APARTMENTS 3 people + 4 people

KasiaRating, 5 stars32 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 stars5 months ago
We loved our stay at Giuliaā€™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.
Top guest favourite
Home in Subbiano
4.99 out of 5 average rating, 78 reviews

Romantic cosy flat - Toscana Italy

DavidRating, 5 stars5 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 AirBnBā€™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 stars5 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:-)
Top guest favourite
Condo in Asciano
5 out of 5 average rating, 163 reviews

Pink like the sunset sky

鹂ēæŽRating, 5 stars1 week ago
very beautiful house, safe and clean. senary is very speic. close to famous sightseeing.

Family-friendly home rentals with a pool

Superhost
Apartment in Cortona
4.6 out of 5 average rating, 5 reviews

Medieval Cottage near Cortona

AnneRating, 5 stars43 months ago
Words canā€™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!!
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 stars6 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!
Superhost
Apartment in Montespertoli
4.89 out of 5 average rating, 9 reviews

12/14 people, WiFi, SW pool, catering

MartinaRating, 5 stars24 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!!
Superhost
Villa in Petrignano
4.98 out of 5 average rating, 51 reviews

Restored Farmhouse & Cottage with AC, Pool & WIFI

JeffreyRating, 5 stars7 months ago
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.
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 stars4 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!
Top guest favourite
Apartment in La Felce
4.98 out of 5 average rating, 107 reviews

La Felce Country House

GarrettRating, 5 stars5 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

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza

LeslieRating, 5 stars3 months ago
Nice agriturismo, very chill place and beautiful surroundings
Superhost
Home in Cortona
4.92 out of 5 average rating, 26 reviews

Beautifully restored villa with private pool

RoxarnaRating, 5 stars5 months ago
Thank you for allowing us to stay at your wonderful accommodation. This was the best place to celebrate my 50th birthday. What wonderful accommodation, facilities and the surrounds of Tuscany. Thank you for your lovely hospitality and making us feel so welcome. Roxy

Quick stats about vacation rentals that are family-friendly in Castellina in Chianti

  • Total rentals

    40 properties

  • Nightly prices starting at

    $57Ā CAD before taxes and fees

  • Total number of reviews

    430 reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Castellina in Chianti
  5. Family-friendly rentals