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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
A well-maintained villa is surrounded by neatly trimmed gardens featuring tall cypress trees and various shrubs. A stone pathway leads to the entrance, and flower pots add subtle touches of color along the pathway. The serene setting is enriched by the presence of green lawns.
Apartment in Orentano
4.94 out of 5 average rating, 32 reviews

Charming apartment in Villa Orsucci Borgo ai Lecci

OonaRating, 5 stars9 months ago
Franco was the best host we’ve ever had! He was very polite and helpful the whole stay. He organized a pasta cooking class and even dropped one of the guests to the airport. The house was amazing, especially the pool area. All in all we would absolutely recommend this place and host!
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
Wir hatten mit unseren Kindern (7 & 9 Jahre) einen wunderschönen Urlaub im Poggio al Cassone. Die Städte Pisa, Lucca, Volterra und Florenz haben wir sehr gut erreichen können. Für die Kinder war der Pool das Highlight nach den Ausflügen. Die gesamte Anlage ist wunderschön gestaltet, das Appartement wirklich gross und es hat uns an nichts gefehlt. Wir können uns gut vorstellen, wieder zu kommen. :)
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 stars3 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 "Le Stagioni di Bacco"

RamonaRating, 5 stars1 week ago
Wir waren als Familie mit Teenagern eine Woche in der Unterkunft und hatten es nicht besser treffen können. Alles war genauso wie beschrieben. Durch das Zimmer im Dachboden, das sich sehr gut klimatisierten ließ, gab es immer die Möglichkeit sich auch mal zurück zu ziehen. Die Unterkunft war blitzsauber. Es gab nicht das geringste zu bemängeln. Wir wurde von Daniele und seiner Familie sehr sehr herzlich empfangen und persönlich verabschiedet. Es gab eine ganze Reihe Tipps für Restaurants und Ausflugsmöglichkeiten. Ich kann das schöne Haus wirklich uneingeschränkt weiterempfehlen. Wir haben uns sehr wohl gefühlt, ganz herzlichen Dank dafür.
Top guest favorite
An aerial view captures the villa surrounded by lush greenery and a well-manicured garden. A spacious pool glimmers in the center, complemented by shaded seating areas. The rustic stone structure is topped with a tiled roof, harmonizing with the serene Tuscan landscape.
Villa in San Gimignano
4.97 out of 5 average rating, 68 reviews

Tuscan villa with pool & hot tub, San Gimignano

SarahRating, 5 stars4 days ago
The villa was simply stunning and we had a wonderful time. The indoor and outside spaces were very spacious and looked exactly as described, if not better! The villa was very clean and Giulia organised everything for us, including pool towels and towel sets. She welcomed us and gave us a tour of the villa when we arrived. I highly recommend Villa Francigena if you want to spend time immersed in the Tuscan beautiful landscape and in a peaceful and spacious typical villa, not far from wine tasting spots and the beautiful town of San Gimignano! Thank you Giulia for a wonderful stay from all of us.
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

JacobRating, 5 stars1 week ago
Samen met mijn vrouw en onze 2 kinderen van 7 en 9 jaar verbleven we een week in het huis van Antonio! Wat hebben wij genoten, echt een week om nooit te vergeten! We kunnen deze plek iedereen aanraden! De tuin is prachtig met vele mooie bloemen en planten. Het zwembad en de jacuzzi zijn nog mooier dan op de foto’s en het huis was voor ons de typische Toscaanse sfeer die wij zochten! We hebben genoten van het adembenemende uitzicht en het terras met bbq en vuurplaats waar we marshmallows met de kinderen hebben geroosterd! Antonio is erg goed bereikbaar en geeft handige tips. En zijn Engels is beter dan dat hij zegt 😉 Wij komen graag nog een terug in dit paradijsje 🤩 Antonio, grazie
Top guest favorite
A wooden chair is positioned beside a round table holding two glasses of red wine, a plate of black grapes, and a rose. Scenic hills are visible in the background, framed by green trees, creating a serene outdoor setting.
Farm stay in Cerreto Guidi
4.95 out of 5 average rating, 62 reviews

Two-rooms Apartment with vineyards view

DanielRating, 5 stars2 weeks ago
Wir sind eine junge Familie mit einem Baby unter einem Jahr und haben uns von der ersten Minute an wohlgefühlt. Gastgeberin Elisa war unglaublich freundlich, hilfsbereit und hatte viele tolle Tipps für Ausflüge und Restaurants in der Umgebung. Das Apartment entsprach genau der Beschreibung und den Fotos – alles war sauber, liebevoll eingerichtet und perfekt für uns. Der Ausblick ist einfach traumhaft: sanfte Hügel, Weinfelder, kleine Wäldchen – genau so stellt man sich die Toskana vor. Nach unseren Tagesausflügen war es für uns und unser Kind ideal, am Abend im Pool zu entspannen. Manchmal haben wir auch einfach den ganzen Tag dort verbracht. Der Pool ist nicht nur eine herrliche Abkühlung, sondern auch ein Treffpunkt für die Gäste – sehr angenehm, um mit anderen Familien oder Reisenden ins Gespräch zu kommen. Wir können diesen Ort – besonders auch für junge Familien – wärmstens empfehlen.

Family- and pet-friendly home rentals

Guest favorite
An outdoor dining area is shaded by a wooden pergola, featuring a large table set with ceramic dishes and glassware. Comfortable metal chairs surround the table, with greenery framing the picturesque view of surrounding hills. A serene atmosphere is enhanced by the natural setting.
Guest suite in Lucca
4.91 out of 5 average rating, 112 reviews

Le Muricciole: the landscape of the gentle hills

GerhardRating, 5 stars5 days ago
Wunderschönes Haus mit schönem Garten oberhalb von Lucca mit Blick auf die toskanische Landschaft. Mit den Rädern war es kein Problem Lucca, Pisa oder den Strand bei Viareggio zu erreichen. Die Wohnung war von der Größe sehr gut für uns sechs Reisende ausgelegt: schöne Zimmer und Badezimmer, absolut perfekt eingerichtete Küche. Überdies stand uns im Garten ein Grill zur Verfügung. Es hat uns sehr gut gefallen.
Guest favorite
Two glasses of white wine are placed on a table beside a swimming pool, surrounded by sun loungers and umbrellas. Tall trees offer shade in the background, while rolling hills can be seen in the distance under a clear blue sky.
Farm stay in Terricciola
4.9 out of 5 average rating, 39 reviews

Two Berdoom apartment @Agriturismo Vallorsi

SaraRating, 5 stars2 days 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!
Guest favorite
The bedroom features vaulted red brick ceilings and warm-colored walls. A spacious bed is positioned against the back wall, with bedside tables on either side. A small window with shutters allows natural light to enter, and a TV is mounted on a shelf for entertainment.
Apartment in Lucca
4.91 out of 5 average rating, 584 reviews

The Mezzanine within the walls

AnnRating, 5 stars1 week ago
We have just returned from a 5 day stay at Gabriele’s apartment. The accommodation was perfect for us, very central, with lots of great places to eat and drink close by. For anyone interested in Lucca’s beautiful parkrun (9am on Saturday morning), the apartment is no more than a ten minute walk away. Many thanks Gabriele.
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

SigridRating, 5 stars2 weeks ago
Sehr freundliche und aufmerksame Gastgeber. Räume hatten eine angenehme Temperatur trotz großer Hitze, traumhafte Gärten um den Landsitz, die zum Verweilen einladen. Wir würden sehr gerne wieder kommen.
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, 181 reviews

Podere Collina

AlexandraRating, 5 starstoday
Beautiful and rustic farmhouse placed in ancient olive grove. We had six adults and were extremely comfortable for our two week stay. Some days we never got out of the clean and refreshing pool. Family dinners were prepared in the perfectly functional kitchen served in the courtyard dining table Nicola was always availableto answer whatever ever came up. Loved the house and our Tuscan vacation
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 stars2 weeks 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 rustic villa features large glass panels that offer views of the surrounding greenery. The spacious outdoor patio area is equipped with a dining set and lounge chairs. Towering trees and well-maintained grass frame the property under a bright blue sky, enhancing the serene countryside setting.
Home in San Miniato
4.92 out of 5 average rating, 104 reviews

Lovely house in a scenic and paiceful location

BiancaRating, 5 stars1 week ago
We hebben genoten van het geweldige huis van Maria. We werden vriendelijk ontvangen door Maria en haar familie, waar we verwelkomt werden met een fles wijn en lekkere taart. We waren met 6 volwassenen. Er is meer dan voldoende ruimte. Fijn dat iedere slaapkamer voorzien is van een eigen badkamer. Het is een prachtig huis in een mooie omgeving met een heerlijk zwembad tussen de olijfbomen en het is echt van alle gemakken voorzien. Erg fijn is ook de oplader voor de elektrische auto. We haalden elke morgen vers brood bij de plaatselijke bakker in het dorpje 5 minuten rijden met de auto. Goede uitvalsbasis voor de mooie steden zoals Lucca, Siena, Florence. Ook het strand is prima te doen. We hebben ons zeer thuis gevoeld. Maria en familie, bedankt voor de geweldige tijd in jullie mooie huis.

Family-friendly home rentals with a pool

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 nel bosco. 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
Superhost
Vacation home in Casole d'Elsa (SI)
4.89 out of 5 average rating, 228 reviews

Studio in Tuscan farmhouse with pool & views

KarolinaRating, 5 stars4 days ago
Moc jsme si užili týden u Fabia. Ubytování je přesně jako na fotkách. Krásná zahrada s bylinkami a výhledy do okolí. Byt má několik různých míst k sezení (u grilu, lavici do zahrady a sezení na západ slunce) a ze všech 3 bytů má nejblíže k bazénu. Bazén příjemně překvapil svou velikostí. Fabio je velmi přátelský, nápomocný a mluví skvěle anglicky. Nabízí možnosti zakoupení vlastního výborného olivového oleje a červeného vína, doporučujeme. Z bytu jsme celý týden pracovali a wi-fi byla bezproblémová i na videohovory.
Superhost
A serene salt-water pool is framed by a stone wall, with colorful flowering plants in the background. The pool features a smooth surface, reflecting the greenery above. A round stone rests on the terracotta patio beside the pool, enhancing the natural setting.
Home in Capannori
4.9 out of 5 average rating, 30 reviews

LA CASA TOSCANE

Marie-ThereseRating, 5 stars2 weeks ago
Wir haben uns bei Isabell sehr wohl gefühlt. Die Wohnung ist sehr hell und sauber. Isabell hat sich mit der Einrichtung sehr viel Mühe geben und überall kleine Aufmerksamkeit platziert. Es gibt sehr gute Empfehlungen für Restaurants/Bars (Sugahero, Gli Orti können wir beides sehr empfehlen) und auch die Katzen auf dem Gelände werden vorgestellt. Das Pool Areal ist sehr clean und bietet viel Schatten, der Garten ist wunderschön durchdacht und ein ruhiger Rückzugsort. Wir würden Isabells Unterkunft auch Freunden empfehlen. Vielen Dank
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.
Superhost
A private pool area is surrounded by landscaped gardens and tall trees, with several lounge chairs positioned nearby. The pool is set on a wooden platform, offering scenic views of the rolling hills in the background under a clear blue sky.
Villa in Gambassi Terme
4.85 out of 5 average rating, 152 reviews

Il Leccio - Tuscany home near San Gimignano

MilaRating, 5 stars1 month ago
Die herrliche Aussicht kann man sowohl als Paar, als auch mit Freund*innen wunderbar genießen. Es ist sehr ruhig und an allem gedacht worden: draußen gibt es sehr bequeme Sitzmöglichkeiten, einen Grill und Pool. Im Garten duftet es überall nach Jasmin. Auch innen fehlt an nichts. Das Haus ist perfekt und befindet sich am perfekten Ort. Nach 20 Minuten Autofahrt erreicht man San Gimignano. Einfach ein Traum und immer wieder eine Reise wert 😍
Superhost
A private patio features a mini pool surrounded by wooden decking. Lush greenery, including olive trees and blooming flowers, enhances the tranquil setting. The rustic stone wall of the house adds a charming touch, while a shaded area provides a comfortable spot for relaxation.
Home in Gambassi Terme
4.8 out of 5 average rating, 60 reviews

Country House Nazzano near Florence/Siena /Ro

OliverRating, 5 stars6 days ago
Beautiful scenery, the place looked even better in real life than in the pictures. Perfect hosts who were friendly and very accommodating. Great location to travel Tuscany. Would have loved to stay longer.
Superhost
Apartment in Larciano
4.9 out of 5 average rating, 117 reviews

Podere Marchiano - Apartment 1

MaximeRating, 5 stars10 months ago
Alessandro nous a accueillis avec beaucoup de patience et de gentillesse. Un hôte très amical que nous prendrons plaisir à retrouver une prochaine année. Ma fille le remercie d'avoir retrouvé son doudou après notre départ, ennième preuve de sa gentillesse.
Guest favorite
An expansive infinity pool reflects the tranquil sky, surrounded by landscaped greenery. Rolling hills can be seen in the distance, enhancing the serene outdoor atmosphere. Sun loungers line the pool area, offering a space for relaxation amidst the Tuscan landscape.
Loft in Marti
4.91 out of 5 average rating, 90 reviews

Rural Loft with magical Tuscan Views

FraukeRating, 5 stars1 week ago
wir haben uns von Anfang an sehr wohl und Zuhause gefühlt. das Loft hat einen einzigartigen Charme und das Gelände mit Pool, Terrasse und Gartenbereich war sehr schön. Wir waren zu jederzeit willkommen, alle waren freundlich und hilfsbereit und auch unsere Kinder sind sehr herzlich aufgenommen worden.

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

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