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Family-friendly vacation rentals in Castiglioncello

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Castiglioncello family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
An aerial view of a charming agriturismo surrounded by lush vineyards. The property includes a pool area with lounge chairs, green spaces, and trees lining the pathways, showcasing a harmonious blend of natural beauty and rustic architecture.
Condo in Crespina
4.94 out of 5 average rating, 47 reviews

Poggio al Casone - Colle

KorinnaRating, 5 stars2 weeks ago
We had a wonderful vacation with our children (7 & 9 years) in Poggio al Cassone. We were able to reach the cities of Pisa, Lucca, Volterra and Florence very well. For the children, the pool was the highlight after the excursions. The entire complex is beautifully designed, the apartment really large and we didn't miss anything. We can well imagine coming back. :)
Top guest favorite
A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.
Cottage in San Gimignano
4.97 out of 5 average rating, 70 reviews

Romantic House in Tuscany with jacuzzi

JosephRating, 5 stars2 weeks ago
Davide and Annalisa's cottage was absolutely gorgeous, exactly as the pictures showed. It was the perfect place for us to relax and enjoy our last week in Italy. Breakfast out on the patio with the birds chirping and surrounded by nature was a great way to start the day. Davide lit the heater for the hot tub for us and we were able to enjoy a wonderful evening relaxing. Davide and Annalisa were full of good recommendations for restaurants and local places to visit. The cottage is within driving distance of so much - Pisa, Florence, Siena and of course San Gimignano just to name a few. All the amenities we needed were included, the WIFI was great and the cottage was very comfortable. I would highly recommended staying here and if we are ever in the vicinity we would certainly stay here again.
Guest favorite
A tranquil outdoor space features a swimming pool with a green and blue float. A dining area with wooden chairs and a colorful table setting is visible, shaded by an umbrella. The house is presented with white shutters and greenery in the surroundings.
Home in Pieve A Nievole
4.95 out of 5 average rating, 147 reviews

La Bruna

IwonaRating, 5 stars1 week ago
Fantastic property, not new but really well kept and looked after. Spectacular outside space with grape vines over a pergola. Pool was a lot bigger than expected and a nice touch. Fabulous greeting and a welcome basket with local treats and Angiolo’s wine. Great location for touring Tuscany. We would definitely go back!
Guest favorite
A charming exterior of a yellow house is visible, featuring arched windows and a welcoming entrance with an awning. A well-maintained garden with blooming flowers enhances the front, while a paved pathway leads to the entrance. The surrounding yard offers fresh greenery.
Home in Monsummano Terme
4.97 out of 5 average rating, 110 reviews

Holiday House "The Seasons of Bacchus"

RamonaRating, 5 stars1 week ago
We stayed as a family with teenagers for a week in the accommodation and couldn't have done better. Everything was exactly as described. Due to the room in the attic, which was very well air-conditioned, there was always the possibility to retreat. The place was sparkling clean. There was no slightest fault. We were very warmly welcomed by Daniele and his family and personally said goodbye. There were a whole range of tips for restaurants and excursions. I can really recommend the beautiful house without reservation. We felt very comfortable, thank you very much for that.
Top guest favorite
The outdoor pool area features clear water with a seating area under a pergola in the background. Sun loungers are arranged around the pool, and greenery enhances the serene environment. A child is seen enjoying the water near the edge of the pool, creating a relaxed atmosphere.
Home in Volterra
4.98 out of 5 average rating, 56 reviews

CountryHouse immersed in woodland

AmirRating, 5 stars2 months ago
One of the best Airbnbs we stayed in with absolutely the best host we have ever met! Antonio was amazing. Before our arrival, he provided clear instructions and suggested to help for a smooth check in. He always made sure that we have what we need for a perfect stay, and even spoiled us with a few complementary wine and chocolate. Now, the place is amazing. From the balcony you get the best views in the region, surrounded by trees and immersed by the sound of birds around you. Truly pleasant, relaxing and restoring vacation. The house is fully equipped with EVERYTHING you need, very well maintained, and super clean. We didn't want to leave, and can't wait to get back again!
Superhost
A coastal view reveals a lush garden with green foliage and rocky shoreline, framed by the blue sea under a clear sky. Terracotta tiles cover a patio area that includes comfortable seating and a shaded spot, inviting relaxation by the water's edge.
Home in Castiglioncello
4.75 out of 5 average rating, 4 reviews

LA CONCHIGLIA, with access to the private sea

EmilioRating, 5 stars58 months ago
The location is special, it reserves a unique view and exceptional livability... you live total privacy immersed in the smells, sounds and colors of the sea!!!
Superhost
The exterior of the farmhouse showcases a three-story stone structure with a rustic charm. Surrounded by a grassy area, the building features a variety of windows and a distinct roofline, with a tree providing shade nearby.
Farm stay in Lucca
4.93 out of 5 average rating, 125 reviews

"La Casa di Gigi" (GG House)

AntonyRating, 5 stars1 week ago
Top notch. Giacomo recommended some great activities to do nearby (after Lucca and Pisa). Very friendly family. Thank you!
Superhost
An infinity pool reflects the surrounding lush landscapes under a clear sky. Large stone formations and trees line the pool, enhancing the serene environment. The horizon features rolling hills, creating a peaceful and expansive view of the Tuscan countryside.
Home in Gambassi Terme
4.67 out of 5 average rating, 72 reviews

Corbezzolo stone cottage, Mummialla

DanielRating, 5 stars9 months ago
A very nice quiet place! Too bad it wasn't very nice and hot during our stay, but we still bathed and enjoyed the wonderful view! Consider bringing mosquito hunting, as there are many. We would go back tomorrow morning if we could:)

Family- and pet-friendly home rentals

Guest favorite
A swimming pool is set within a lush green landscape, bordered by a stone path. Sun loungers are arranged around the pool, with a shaded gazebo nearby. The surrounding area features trees and a fence, offering scenic views of the valley in the distance.
Vacation home in Matraia
4.91 out of 5 average rating, 106 reviews

"IL FIENILE" rustic stone house

SandraRating, 5 stars2 weeks ago
Our stay at Marina and Paolo’s hilltop home in the Tuscan hills was nothing short of magical. The house is a true piece of paradise, immaculately clean, with breathtaking views that left us in awe every day. Marina and Paolo were incredibly kind hosts, making us feel completely at home. The swimming pool was fantastic, and the entire experience immersed us in the charm of Tuscan life. We highly recommend this gem to anyone looking for an unforgettable getaway!
Guest favorite
The exterior of a two-story, Tuscan-style apartment is visible, featuring light-colored walls and traditional wooden shutters. A welcoming staircase leads to a balcony adorned with potted plants, providing access to the upper level. Greenery surrounds the entrance, adding to the tranquil ambiance.
Condo in Gambassi Terme
4.89 out of 5 average rating, 234 reviews

A View Over Tuscany's Countryside

CarolinaRating, 5 stars3 weeks ago
Incredible experience! Filippo’s place was as described! All the amenities present and spot clean. We really enjoyed our stay and recommend to everyone!
Superhost
A spacious swimming pool is surrounded by sun loungers and umbrellas, set against a backdrop of olive trees. The clear blue water reflects the sky, and stone pathways lead around the pool area, providing a tranquil outdoor space for relaxation.
Farm stay in Vinci
4.87 out of 5 average rating, 108 reviews

Tuscan apartment with pool ,garden and barbecue

BhavinRating, 5 stars2 weeks ago
Staying at Lorenzo and Eva’s place was an absolute highlight of our trip to Tuscany! The location was exceptional, it offered breathtaking views of the Tuscan countryside that we’ll never forget. Just a short drive away is the charming town of Vinci, where you’ll find everything you need to make the most of your stay. The wine and olive oil tasting experience is an absolute must—it added such a special touch to our visit. The property itself is beautifully maintained, with excellent amenities that made our stay comfortable and relaxing. Lorenzo and Eva were both very professional, and their communication was always prompt and helpful. We can’t wait to return to Vinci and would love to stay at their place again!
Guest favorite
The rustic villa is nestled among lush greenery, featuring stone walls and a traditional roof. Surrounding olive trees and rolling hills enhance the natural beauty, while the clear blue sky adds to the serene countryside setting.
Farm stay in Ulignano
4.9 out of 5 average rating, 135 reviews

A few steps from Volterra, La Rosa Apartment

桂子Rating, 5 stars2 weeks ago
Nice antique house in a wonderful environment.The large garden is well maintained and there is a beautiful view of the town of Portera.Delicious mountain spring water that is always flowing.It's full of good things 。
Guest favorite
A rustic stone house is viewed from the garden, surrounded by lush green grass and trees. The warm tones of the structure contrast with the vibrant foliage, highlighting the serene outdoor environment. A stone pathway leads to the entrance, inviting exploration of the property.
Apartment in Cascine-La Croce
4.88 out of 5 average rating, 147 reviews

Casa Belvedere #2 between Pisa and Lucca

MichaelRating, 5 stars3 weeks ago
We had a very relaxing week at Franco’s property. The place was well appointed including the full kitchen and we really enjoyed sitting outside with a glass of wine looking over the beautiful countryside. A perfect retreat. Highly recommended
Top guest favorite
The rustic stone house features a facade adorned with climbing greenery, offering a blend of natural beauty and architectural charm. Large wooden doors open onto a welcoming terrace, which is surrounded by greenery, providing a serene outdoor space for relaxation.
Home in Volterra
4.93 out of 5 average rating, 180 reviews

Collina Power

DeanRating, 5 stars4 weeks ago
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!
Guest favorite
A spacious terrace features a large umbrella providing shade over a table and chairs. Surrounding flowering plants create a vibrant atmosphere, while a pair of lounge chairs invites relaxation. The area is complemented by a clear blue sky, enhancing the outdoor experience.
Home in Pisa
4.91 out of 5 average rating, 610 reviews

Relax on the terrace near the Tower

StevenRating, 5 stars1 week ago
Lovely little place, super location with everything you need for a pleasant visit. Nice roof garden to sit and dream. Clean and well looked after. Many thanks - also a short walk to the tower.
Guest favorite
A landscaped garden features a swimming pool surrounded by sun loungers and umbrellas. A stone pathway leads through the greenery, with trees and potted plants visible. The scenic view showcases rolling hills and distant mountains, under a bright blue sky.
Home in Fibbiano
4.96 out of 5 average rating, 149 reviews

House in Tuscany with pool

RobertRating, 5 stars3 weeks ago
Cristina is the perfect host and the house is beautiful. The surroundings are amazing and the views......wow! All through the booking and our stay there Cristina was swift to answer any questions we had and also was happy to offer suggestions on places to go and where to eat. We had a perfect week there and I wouldn't hesitate to go back or to recommend her place to anyone else. Cristina and her sister met us at the house and showed us round, clearly pointing out all the relevant bits that we would need to know. Thank you so much for making our week in Italy so special and enjoyable......we are already looking to come back!

Family-friendly home rentals with a pool

Guest favorite
An outdoor swimming pool is surrounded by lounge chairs, complemented by bright red umbrellas. Lush greenery encircles the area, and a clear blue sky with fluffy clouds adds to the serene atmosphere. The building, set in the background, features a rustic design.
Farm stay in Vada
4.89 out of 5 average rating, 55 reviews

Two-room apartment with pool near the sea

FethiRating, 5 stars1 week ago
We have just returned from our Italian vacation and would like to say a few kind words about our wonderful host Pietro. Pietro is a very friendly and warm person – thanks to him we never felt like strangers. He gave us a lot of helpful information even before we had to ask. We loved the products from his garden and took fresh fruits and vegetables and olive oil from his own cultivation with us when we left. As soon as you enter the accommodation, you will be greeted by the beautiful olive trees in the courtyard – simply fantastic! We sincerely hope to see you again one day. Pietro, we send you and your family our best regards! :) Tugba/Fethi and Eylül
Top guest favorite
A serene pool area is surrounded by lush greenery, featuring a rectangular swimming pool with light blue water. Several lounge chairs are arranged neatly on the pool deck, with a large tree providing shade in the background. The scene is bright and open, inviting relaxation.
Apartment in Livorno
4.99 out of 5 average rating, 80 reviews

La Luna in the woods. Rooftop terrace & seasonal pool.

JakobRating, 5 stars2 weeks ago
The accommodation was perfect - we had a calm, quiet apartment to rest and hang out by the pool or on the terrace. From there we made trips to different beaches and cities, which was convenient. Alessandra was so kind to us, gave us recommendations and helped with local tips
Guest favorite
Farm stay in Terricciola
4.9 out of 5 average rating, 39 reviews

Two Berdoom apartment @Agriturismo Vallorsi

SaraRating, 5 stars1 day ago
We had 8 wonderful days at Vallorsi, and didn’t wanna leave. Lovely pool, wine tasting, friendly people and just amazing views and environments. Tasty wines and beverages was available against pay when checking out which was convenient since you needed a car to go to the store. However - The store, big and well sorted, was just 5 km away We will be back for sure!
Top guest favorite
The outdoor pool area features a clear blue pool surrounded by a spacious lawn and blooming roses. Lounge chairs are arranged neatly under white umbrellas. A pergola is visible in the background, enhancing the scenic view of the countryside.
Farm stay in Castelfiorentino
4.93 out of 5 average rating, 153 reviews

Amazing view, pool and relax, 5 adults

VarshaRating, 5 stars2 weeks ago
**Unforgettable Stay with Perfect Pool and Stunning Views** This BNB met our expectations during our family trip to Italy. The property was clean throughout, and the hosts went above and beyond with their hospitality - greeting us warmly in person and thoughtfully providing welcome snacks and a bottle of wine. The pool is absolutely perfect and became the centerpiece of our stay. Some of my most cherished memories from our entire Italy trip were spent relaxing by the pool with my family. The sunset views from the property are breathtaking and provided the perfect backdrop for our evenings. Both sisters who run this place are genuinely wonderful people who clearly care about their guests' experience. Their personal touch made our stay feel special and welcoming.
Top guest favorite
An inviting swimming pool reflects the surrounding landscape, bordered by a wooden deck with several lounge chairs. Sun umbrellas provide shade, while lush greenery and mature trees fill the background, enhancing the serene outdoor setting.
Villa in Lucca
4.98 out of 5 average rating, 80 reviews

Villa Marì

SamuelRating, 5 stars2 weeks ago
We had an absolutely wonderful stay at this beautiful villa in Lucca! The property is stunning, with breathtaking views of the surrounding countryside that made every morning feel like a dream. The villa itself is spacious, clean, and tastefully decorated, striking the perfect balance between rustic charm and modern comfort. Our hosts were incredibly welcoming and attentive—they went above and beyond to make sure we had everything we needed and offered great tips for local spots to explore. It was clear they truly cared about creating a memorable experience for their guests. Most of all, the peaceful atmosphere made it the perfect place to relax and unwind. Whether enjoying a glass of wine on the terrace or simply soaking in the scenery, it was exactly the getaway we were hoping for. We can’t wait to come back!
Guest favorite
A serene swimming pool reflects the blue sky and surrounding greenery. Lounge chairs line the pool's edge, facing a charming house with a broad, inviting terrace. The tranquil atmosphere is enhanced by lush landscaping and clear water, creating an inviting space for relaxation.
Apartment in Castagneto Carducci
4.83 out of 5 average rating, 89 reviews

Apartment Mimosa - Tuscany

MichałRating, 5 stars6 days ago
I highly recommend this place to all guests. Valentino and his mother are exceptional hosts. The entire place feels like something out of a fairytale—quiet, calm, and beautiful. You’ll find everything you’re looking for here and can fully escape the worries of daily life. Don’t hesitate—book it immediately when it’s available!
Superhost
A serene outdoor area features a clear swimming pool, surrounded by lush greenery and neatly arranged landscaping. The stone house has a spacious balcony above, offering additional seating options and views of the countryside.
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 People - Private Pool

ShemaiahRating, 5 stars10 months ago
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.
Guest favorite
The kitchen area features a rustic wooden ceiling and terracotta flooring. A dining table is set for four, with glassware and tableware arranged neatly. An open window allows views of the surrounding hills, while a counter displays bottles of wine and a few cooking essentials.
Apartment in Querceto
4.82 out of 5 average rating, 28 reviews

Apartment in the countryside with view and pool

JenayeRating, 5 stars3 weeks ago
Amazing location and beautiful location

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

  • Total rentals

    140 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore