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Family-friendly vacation rentals in Castiglione della Pescaia

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Castiglione della Pescaia family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A round jacuzzi filled with water is shown, surrounded by lush greenery and hills in the background. The scene captures a serene atmosphere, with part of the jacuzzi featuring a built-in space for drinks.
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars6 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Guest favorite
The image showcases a charming villa set amidst lush greenery, featuring a stone pathway leading to the entrance. A private swimming pool reflects the sunshine, while colorful flowers add vibrancy to the surrounding landscape. The rustic building displays traditional Tuscan architectural elements.
Farm stay in Sovicille
5 out of 5 average rating, 23 reviews

Tuscan Villa:Pool,Hot Tub,A/C,wi-fi,7bd near Siena

TimRating, 5 stars9 months ago
Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place
Superhost
A serene pool area features a curved, salt-water pool framed by a white railing. Light drapes billow gently in the breeze, enhancing the tranquil setting. The surrounding landscape includes rolling hills under a clear blue sky.
Home in Campo nell'Elba
4.9 out of 5 average rating, 147 reviews

Relax in the countryside near the sea( Lavanda )

AntonelloRating, 5 stars2 weeks ago
Isabella è una persona simpatica e alla mano, ci ha accolto nella sua splendida villa mettendoci subito a nostro agio. Ottimi i suoi consigli sui luoghi da visitare e dove mangiare. L'alloggio dispone di tutti i confort, bellissima la piscina salata, purtroppo non disponibile non essendo ancora iniziata la stagione. Ci ritornerò sicuramente, grazie di tutto Isabella!
Guest favorite
The exterior of the property features a rustic stone façade complemented by wrought iron details. A spacious terrace is equipped with a large umbrella and an outdoor dining area, surrounded by lush greenery, enhancing the natural setting.
Cottage in Radicondoli
4.92 out of 5 average rating, 131 reviews

Splendido fienile ristrutturato in Toscana

GabrieleRating, 5 stars2 months ago
Casetta incantevole all’interno di un grande bosco. Ideale se cercate relax e tranquillità. Posizione ottima se amate il trekking e gli animali selvatici. La vasca idromassaggio esterna permette di rilassarsi sotto le stelle. Camino e cucina attrezzatissima rendono confortevole l’interno della casa. Gloria e Giorgio sono state persone super disponibili ed educatissime
Superhost
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, 255 reviews

Charming estate with views

LisaRating, 5 stars5 days ago
Wir hatten einen wunderschönen Aufenthalt bei Bernadino! Das Haus ist sehr gemütlich und toll gelegen mit einmaligem Blick auf die Weinberge. Der Garten ist sehr schön angelegt und der Jacuzzi ein absolutes Highlight! Wir haben von Bernadino gute Tipps für die Umgebung bekommen und an einem Abend leckeres toskanisches Essen bekommen. Das Haus ist gut ausgestattet und typisch toskanisch. Wir wären gerne noch länger geblieben :) Vielen Dank!
Superhost
The image captures a serene landscape featuring a lush green lawn bordered by dark green trees. A small heated mini pool is positioned nearby, providing a relaxing view of rolling hills under a partly cloudy sky. The peaceful atmosphere is enhanced by the natural surroundings.
Condo in Ponteginori
4.87 out of 5 average rating, 15 reviews

Romantico e accogliente bilocale

GabriellaRating, 5 stars8 months ago
Splendido luogo tra Cecina e Volterra per soggiornare in piena tranquillità e relax tra le colline toscane, panora e tramonto fantastico. Comodo per visitare borghi medioevali e non lontano dalla famosa costa degli etruschi e per chi ama le città si può raggiungere Pisa e Siena. Fausto è un host fantastico, preciso e disponibilissimo, ma non invadente, ci ha fornito indicazioni sui luoghi da visitare, le spiagge tipiche e anche i ristorantini molto carini nelle vicinanze. Il nostro soggiorno è stato piacevole e rilassante quello che desideravamo era stare lontano dalla confusione e dallo stress quotidiano, se questo è quello che cerchi qui lo trovi ...sentirai solo il "rumore" delle cicale.
Guest favorite
A ground-level countryside dwelling is presented with natural stone pathways and wooden shutters. Potted plants are positioned near the entrance. The exterior is complemented by expansive windows, providing views of the surrounding landscape under a clear blue sky.
Home in Catabbio
4.89 out of 5 average rating, 158 reviews

Country house La Meria

DamonRating, 5 stars6 months ago
We are an American and Italian family traveling through Italy and we highy recommend this special spot in the mountains. The landscape was beautiful and the breakfast was wonderful. We ended up arriving very late in the evening as their was a crash on the autostrada and Luca was very accommodating and communicative. We would stay here again.
Top guest favorite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 129 reviews

Villa di Geggiano - Guesthouse

LauraRating, 5 stars3 weeks ago
The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!

Family- and pet-friendly home rentals

Superhost
A panoramic view of Sasso Pisano is captured, featuring historic stone buildings nestled among lush green hills. The clock tower stands prominently, while tree-covered slopes provide a natural backdrop, highlighting the town's rustic charm and tranquil setting.
Apartment in Sasso Pisano
4.78 out of 5 average rating, 189 reviews

La Maison di Monica & Simona

JurgitaRating, 5 stars1 week ago
Viešnagė labai patiko: būstas erdvus ir jaukus (dar gražesnis, nei nuotraukose :)), buvo viskas, ko reikia: patalynė, rankšluosčiai, viskuo aprūpinta virtuvė. Šeimininkai draugiški ir, nors nedaug kalba angliškai, bet viską paaiškina :)... Miestelis irgi žavus - kupinas istorinio dvelksmo. Visai netoli (nuo būsto gal 5 min. pėsčiomis) yra nedidelė terminė versmė - gana karšta, tad tik vienas iš mūsų maudėsi, bet kojas pamirkėme visi ;)... Miestelio bare vaišinomės vynu - buvo labai malonu pabendrauti su vietiniais gyventojais. Žodžiu, šilčiausi atsiliepimai - ačiū už viską!
Top guest favorite
An open living space features a colorful polka-dotted sofa and a small dining table surrounded by vibrant chairs. The kitchen area is organized with shelves displaying kitchenware and appliances, with a warm wooden ceiling enhancing the cozy atmosphere.
Apartment in Pienza
4.9 out of 5 average rating, 163 reviews

Back Home - Apartment in Pienza

MorganRating, 5 stars1 month ago
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!
Top guest favorite
A shaded outdoor seating area is surrounded by lush greenery and flowers, featuring two woven chairs and a hammock hanging from a tree. The background offers a view of the coastline and distant hills, creating a peaceful retreat.
Vacation home in Porto Azzurro
4.89 out of 5 average rating, 35 reviews

La casa di Emma apt "Terra"

JoachimRating, 5 stars9 months ago
Der Aufenthalt bei Elena war etwas besonderes. Die Lage bot viel Ruhe mit einem tollen Blick auf das Meer. Der Style und die Kühle des Hauses im Sommer, die schattigen und Lounge-artigen Plätze ausserhalb boten fast eine Art Club-Atmosphäre. Der "Preis" dafür sind ca. 20 Minuten Fussweg bis zum Hafen von Porto Azurs.
Guest favorite
Farm stay in Bucine
4.98 out of 5 average rating, 43 reviews

Boggina. Private villa with pool, walk to village

AnnaRating, 5 stars7 months ago
Boggina was such a beautiful setting for our two families. There is no air conditioning, but the house kept beautifully cool by using the shutters in the day and using fans at night. The bedrooms were dreamy, full of trinkets from families past. The pool was fantastic and we enjoyed a lovely wine tasting tour! We basically didn’t want to leave! Many thanks team Marco 😊
Guest favorite
The exterior of the property showcases a covered terrace bordered by lush greenery. A stone barbecue is positioned beside the terrace, with a paved pathway leading to the entrance. Wooden seating is visible, providing an inviting outdoor space.
Apartment in Marciana
4.79 out of 5 average rating, 100 reviews

Casa Piccola

KarinRating, 5 stars8 months ago
Die Wohnung haben wir sehr sauber und wie beschrieben angetroffen, und die Gastgeber waren sehr freundlich. Sie haben uns bei der Ankunft Tipps für Ausflüge gegeben. Anna Maria und ihr Mann haben hier ein kleines Paradies gestaltet. Wer Ruhe sucht, wird diese in dieser wunderschönen Umgebung auch finden. Die Terrasse ist nicht nur für Sonnenuntergänge perfekt, sondern auch für den Blick in den Sternenhimmel! Der Platz war für uns mit zwei Kindern ausreichend, da wir sowieso meist draussen waren. Den kleinen Laden im benachbarten Colle d'Orano können wir empfehlen. Wir haben die Woche in Patresi sehr genossen!
Superhost
A serene pool reflects the vibrant colors of the sunset, with gentle waves suggesting a peaceful ambiance. Lush greenery surrounds the area, creating a natural setting. The silhouette of a building and a lone tree can be seen in the background against the colorful sky.
Home in Staggia
4.87 out of 5 average rating, 39 reviews

Vacanza nel Chianti Senese

JosefinRating, 5 stars9 months ago
We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.
Superhost
Vacation home in Porto Santo Stefano
4.83 out of 5 average rating, 35 reviews

Villino Mare nel sole

BrigitteRating, 5 stars9 months ago
Wir hatten eine wunderbare Woche im Ferienhaus von Ale, mit direktem weitem Blick aufs Meer und 2 Inseln. Ale sandte eine sehr genaue Beschreibung, wie man zu Ihr findet, incl. Fotos von den wichtigsten Abzweigstellen. Es war einfach zu finden für uns. Wir waren mit einem SUV und 2 E-Bikes da, den Parkplatz zu unserem Chalet konnten wir damit gut erreichen, auch die etwas steilere Straße runter zum Chalet. Für alle Fahrzeuge, die keinen höheren Radstand haben, gibt es oberhalb von Ales Haus einen Parkplatz, man ist in 3 -4 Minuten zu Fuß unten. Ale hieß uns herzlich willkommen, und versorgte uns mit Tips für Restaurants und Strände in der näheren Umgebung. Unser Chalet hatte alles, war wir brauchten zu zweit. 2 Terrassen, davon eine mit Outdoorküche, im Schlafzimmer gibt es eine Klimaanlage, die wir zum Einschlafen nutzten. Den Blick über das Meer bis zu den Inseln haben wir von morgens bis abends genossen, es gab immer etwas zu sehen. Wir hatten eine tolle Zeit, danke Ale!
Guest favorite
A spacious living area features a wooden-beamed ceiling and large windows allowing for natural light. A red sofa and rustic wooden table create a comfortable setting. A stone fireplace is positioned in the corner, adding a warm element to the welcoming environment.
Home in Gaiole in Chianti
4.8 out of 5 average rating, 100 reviews

loft nel cuore del chianti toscano

CharlotteRating, 5 stars6 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.

Family-friendly home rentals with a pool

Guest favorite
A modern villa with a unique architectural design features large glass windows reflecting the pool's surface. The turquoise infinity pool is surrounded by lounge chairs and an umbrella, offering an inviting outdoor space with lush greenery in the background.
Villa in Rosignano Marittimo
4.92 out of 5 average rating, 25 reviews

Villa Castiglioncello - accesso al mare privato

JürgRating, 5 stars7 months ago
Haus, Lage: direkt am Meer, traumhafte Aussicht, spektakuläre Sonnenuntergänge, grosses Haus mit besonderer Architektur bietet viel Raum und Privatsphäre, ideal für eine grosse Familie. Verschiedene Garten- Terrassenzonen. Alles sehr gepflegt und bestens ausgestattet. Camilla ist eine sehr herzliche und kompetente Gastgeberin. Wir kommen gerne wieder!
Guest favorite
Villa in Pergine Valdarno
4.82 out of 5 average rating, 17 reviews

Exclusive Villa with Private Pool and Air Cond.

KaraRating, 5 stars10 months ago
Our stay at Villa Chiara was nothing short of delightful. Nestled in the hills it offered a picturesque view of the Tuscan countryside. The villa itself was spacious and well maintained. It felt like home away from home. The pool and back patio are surrounded by lovely flowers, herbs and olive trees. Offering a spectacular view of the evening sunsets. The location was perfect to take short day trips to Siena, Florence and Montepulciano. Highly recommend for a serene, peaceful and relaxing getaway.
Guest favorite
A well-maintained pool area features a clear swimming pool in the foreground. Sun loungers are positioned beside the pool, shaded by umbrellas. In the background, the farmhouse with blue shutters is surrounded by lush gardens and trees, offering a serene outdoor space.
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

ClemensRating, 5 stars7 months ago
Wir hatten einen tollen Urlaub mit 9 Freunden. Das Haus liegt sehr ruhig und ist sehr hochwertig und liebevoll eingerichtet. Der Außenbereich war wunderschön und grün. Ein toller Pool und viel Platz ganz für sich alleine. Alles exakt wie beschrieben und auf den Bildern gezeigt. In der Nähe sind mit dem Auto viele schöne und günstige Restaurants erreichbar. Wir würden es auf jeden Fall weiterempfehlen und hatten eine schöne Zeit. Amanda war sehr freundlich und war immer schnell erreichbar bei Fragen.
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars6 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!
Guest favorite
A tranquil pool with clear blue water reflects the sky, surrounded by lush greenery and colorful flowers. Rolling hills and a scenic landscape are visible in the background, enhancing the serene environment of the property.
Apartment in Sovicille
4.9 out of 5 average rating, 131 reviews

Apartment for 2 with super views+pool near Siena

JanRating, 5 stars7 months ago
Mario war sehr herzlich und ein sehr sehr toller Gastgeber. Wir würden immer wieder kommen!
Superhost
Apartment in Siena
4.71 out of 5 average rating, 7 reviews

Splendid house with garden, pool, 5km from Siena

AlbertoRating, 5 stars3 weeks ago
Ideal para unas vacaciones familiares en la Toscana. Entorno idílico rodeado por colinas y viñedos. La casa estaba impecable u la atención de Lavinia excelente!
Superhost
Home in Piombino
5 out of 5 average rating, 13 reviews

Tra mare e tradizione, vacanza antistress!!!

AlbertoRating, 5 stars8 months ago
I've spent 10 days of relax with my family, we had great time, the place is very quiet and relaxing. Very clean and tidy. Air conditioned helped us in the hottest days. It's very convenient to the sea, although we spent our days of holiday by the pool. Highly recommended!!!
Superhost
Apartment in Prato d'Era
4.9 out of 5 average rating, 20 reviews

Apartment 2doublerooms private fenced garden, pool

LucileRating, 5 stars8 months ago
Nous avons passé un agréable séjour chez Silvia. Nous sommes restés 2 semaines ce qui nous a permis de découvrir le Toscane. Nous avons eu un problème avec le frigo. Silvia et son mari ont été très réactifs. Nous avons eu la chance de découvrir la famille de Silvia via un cours de cuisine dans agroturismo de ses parents. On a adoré ! Le logement était très propre et spacieux. Nous avons bien apprécié la piscine avec la chaleur. Volterra est à 10 minutes en voiture. Et les paysages sont magnifiques.

Quick stats about vacation rentals that are family-friendly in Castiglione della Pescaia

  • Total rentals

    230 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    140 properties include access to wifi

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