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Family-friendly vacation rentals in Castellina in Chianti

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Popular amenities for Castellina in Chianti family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A bedroom features a decorative iron headboard against a soft green wall. Two well-made beds are adorned with white linens and embroidered pillows. A bedside lamp provides soft lighting, while a wooden cabinet and door add a rustic touch to the space.
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!
Guest favorite
An outdoor space features a round hot tub surrounded by a wooden deck. Colorful lounge chairs provide seating, with a vibrant red and orange combination standing out against the green lawn. Olive trees dot the landscape, offering a serene view of the surrounding hills.
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
The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.
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.
Top guest favorite
Well-maintained gardens feature a lush lawn surrounded by mature trees, providing shade. An old stone building is visible in the background, characterized by arched windows and a terracotta roof. A shaded outdoor seating area, under a rustic wooden eave, adds to the inviting exterior.
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
A sunlit sunroom features large windows adorned with sheer curtains, allowing natural light to fill the space. A cozy white sofa is positioned next to a small wooden table with chairs, while indoor plants add a touch of greenery to the inviting atmosphere.
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
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa
4.94 out of 5 average rating, 171 reviews

Wheelchair accessible Villa with Jacuzzi

KristinRating, 5 stars1 week ago
This was such a beautiful stay in Tuscany. When our family arrived it was magical to them to be in Beatrice’s home and countryside. It’s full of history and breathtaking views.
Guest favorite
A spacious living area features a large wooden table set for a meal, adorned with fresh fruits and glassware. A comfortable red couch is positioned nearby, complemented by framed black and white photographs on the wall and stylish pendant lights above.
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
A serene garden scene features a table set with a floral-patterned teapot and matching cups. Lush greenery surrounds the area, with terracotta pots and vibrant flowers enhancing the natural setting. The space is bathed in soft sunlight, providing a tranquil outdoor retreat.
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

Family- and pet-friendly home rentals

Top guest favorite
The image displays a tranquil outdoor setting featuring a stone swimming pool surrounded by lush greenery. In the background, a historic tower rises among tall trees, while olive trees are seen in the foreground, enhancing the natural beauty of the landscape.
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
A serene bedroom space features a spacious bed adorned with soft, neutral-toned linens. Sheer white drapes create a cozy atmosphere, while the open doors offer a view of the lush outdoors, inviting natural light into the room.
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Explore nature in the center of Vigneti Chianti

BaileyRating, 5 stars1 week ago
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.
Top guest favorite
The exterior of a rustic stone building is showcased, featuring traditional wooden shutters and a charming door. Potted plants and climbing vines adorn the entrance, while a small outdoor seating area with a table and chairs is visible on the green lawn.
Farm stay in Siena
4.97 out of 5 average rating, 275 reviews

Authentic Tuscan Country House WITH A/C

JamesRating, 5 stars1 week ago
The apartment was exactly as advertised. In fact, not sure the pictures do it justice. It is a beautiful setting - peaceful and relaxing. The space in the apartment was very usable with two bathrooms and a nice kitchen. Martina was super helpful and communicated well with fast response time. Great recommendations for walks and restaurants. I can’t say enough nice things about her. Just an ideal host.
Guest favorite
The image captures a green hillside landscape, with a stone farmhouse situated at the center. Lined cypress trees create a pathway in the background, while the garden surrounding the home features a pool. The sky is clear and bright, enhancing the serene environment.
Farm stay in Campiglia D'orcia
4.94 out of 5 average rating, 414 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

RodrigoRating, 5 stars1 day ago
Beautiful place, lovely host. One of the best airbnb experiences I’ve had!
Top guest favorite
The image captures a serene outdoor setting featuring a swimming pool surrounded by a well-maintained lawn. Several sun loungers positioned around the pool invite relaxation, while the rustic house and lush greenery complete the idyllic scene.
Vacation home in Panzano
4.97 out of 5 average rating, 150 reviews

Fienile Santa Teresa

ZoeRating, 5 stars4 days ago
Christine and John were the best hosts, making this incredible location even more enjoyable. They went above and beyond, recommending restaurants, wineries and experiences that made our trip unforgettable. Christine also helped us get our lost luggage back, ringing the airport for us and liaising with a driver in Florence to pick it up and drop it off to us. Incredible service. Absolutely recommend!
Top guest favorite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Apartment in Montepulciano
5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

MarkRating, 5 stars1 month ago
My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!
Superhost
A serene outdoor area features a swimming pool with clear blue water, bordered by wooden decking. Four lounge chairs face a vibrant garden of yellow flowers, offering expansive views of the surrounding hills and sky filled with fluffy clouds.
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
A tranquil outdoor pool is surrounded by well-maintained gardens and olive trees. Sun loungers are positioned along the poolside, providing space for relaxation. The stone-clad building in the background complements the landscape, contributing to the serene environment.
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. :)

Family-friendly home rentals with a pool

Top guest favorite
A refreshing swimming pool is framed by neatly arranged lounge chairs and sun umbrellas, surrounded by vibrant greenery and a hedge. Scenic hills and a clear blue sky serve as a backdrop, providing a tranquil outdoor space for relaxation and enjoyment.
Vacation home in San Donato In Poggio
4.98 out of 5 average rating, 140 reviews

Chianti Penthouse with panoramic View & Pool

AntoniaRating, 5 stars1 month ago
Giada's penthouse apartment was the perfect spot for a relaxing stay in Tuscany. Accessible to so many Chianti vineyards, we only wish we'd had more time staying there to explore, and less rainy weather, to enjoy the on site amenities like the pool and the two balconies more. She also gave us recommendations for the area which were super helpful! We would happily stay again.
Top guest favorite
Farm stay in Pisa
4.99 out of 5 average rating, 298 reviews

Tenuta Chiudendone in Tuscany

KarenRating, 5 stars6 days ago
Wonderful place for a family and to recharge in our busy trip to Italy. Sign up for the farm to table experience when you stay. The hosts could not have been more helpful and wonderful. Beautiful property and accommodation.
Guest favorite
A spacious outdoor pool is surrounded by lush greenery, featuring olive trees and vibrant plants. The pool's crystal-clear water reflects the sky, while a sun terrace with lounge chairs is available for relaxation. The serene landscape enhances the tranquil atmosphere of the setting.
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
Guest favorite
The stone cottage is set amidst lush greenery, featuring a sloped roof and a large glass door that opens onto a sunlit terrace. Sun loungers are positioned nearby, surrounded by flowering plants, with olive trees visible in the background against a clear blue sky.
Farm stay in Cavriglia
4.92 out of 5 average rating, 336 reviews

Chianti La Pruneta, Raphael Apartment

KathleenRating, 5 stars1 week ago
Very friendly and helpful host, Massimo made us feel at home. A beautiful apartment overlooking some incredible views. Lovely clean pool. Just a perfect holiday all round!
Superhost
A serene outdoor pool is surrounded by lush greenery, with sun loungers positioned nearby. The sun casts a gentle light on the water, creating a tranquil atmosphere. Foliage frames the scene, enhancing the natural setting among the trees.
Farm stay in Monteriggioni
4.82 out of 5 average rating, 149 reviews

Podere Casalino - La Pergola

GeorgieRating, 5 stars9 months ago
Laura and Jeremy’s Airbnb is so special and we are so glad we had 5 nights here. It’s the location, the house, it’s surrounding, the vegetable patch, dogs, incredible pool and Laura + Jeremy themselves that make it so lovely. The villa became our home base and was so peaceful and calm with everything we needed. It was the type of experience that made us want to move in forever. Jeremy even brought us fresh tomatoes and herbs from the garden, bellissimo! If you are reading this review, please do yourself a favour book. Recommend a hire car and buying produce to cook up some delicious meals to eat under the Tuscan sun 🌞
Top guest favorite
A spacious outdoor swimming pool is surrounded by a patio made of terracotta tiles. Sun loungers are placed nearby under a shaded pergola. Lush greenery and trees frame the area, providing a serene view of the villa set atop a hill in the background.
Farm stay in Palaia
4.98 out of 5 average rating, 169 reviews

Countryside Dream farm in Tuscany

MercedesRating, 5 stars6 days ago
We had the most magical stay at this Tuscany farm! The property is absolutely stunning — nestled among rolling vineyards and olive groves, with postcard-perfect views in every direction. Our apartment was spacious, charming, and had everything we needed for a comfortable stay. The hosts were incredibly kind and welcoming, sharing local recommendations. Our kids loved meeting the animals, exploring the grounds, and especially swimming in the beautiful pool overlooking the hills — it was a total dream! Evenings on the terrace with a glass of wine and the Tuscan sunset were unforgettable. This was a once-in-a-lifetime experience for our family, and we can't wait to return. Highly recommend to anyone looking for a peaceful, authentic Tuscan escape! 🌿🍷☀️
Guest favorite
A shared swimming pool is surrounded by stone paving and offers a clear view of the hills in the background. Sun loungers are positioned on the poolside, inviting relaxation amid natural scenery under a bright blue sky.
Farm stay in San Gimignano
4.89 out of 5 average rating, 209 reviews

Oleandro double room with pool in San Gimignano

EricaRating, 5 stars1 week ago
While Paolo was away, our check-in and communication with Bruno went very smoothly. The property is absolutely stunning. The view of Sam Gimignano as you swim in the pool was something out of a movie scene. The property has surrounding olive trees and vineyards seen right from the window of the airbnb. This particular room is in a tucked away corner of the property and feels very private. Bed was comfy. Washing machine and drying racks, as well as a grill were plusses. Many agriturismos offer a dinner for an added fee, and we were a little disappointed that the dinner (in the past offered by Paolo’s neighbors) was closed during our stay. However, in fending for ourselves, we did appreciate the mini fridge and microwave, and loved eating our dinner right on the private table outside the room door. Also, you do have to clean out your trash at the end of the stay. Price felt right. Overall, would happily stay again and will be forever dreaming of the view.
Guest favorite
Apartment in Greve in Chianti
4.9 out of 5 average rating, 107 reviews

casa mezzomonte Apt Timo

JisunRating, 5 stars2 weeks ago
I had a happy time in a house that looked like it was in a movie in a beautiful natural environment. I think I will keep my time in Kian Tti as a good memory thanks to the kind and friendly host who responds so quickly. It was a little difficult at first for the city girls who were new to the road to the accommodation, but it wasn't difficult when they got used to it. It's perfect for watching the sunrise and sunset. I left today, but I want to go again.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$2,092 GYD before taxes and fees

  • Total number of reviews

    440 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

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