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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
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.
Superhost
A terrace features a simple table set with two white chairs, offering a view of the lush greenery beyond. An awning provides shade, while a blue sky with scattered clouds creates a serene atmosphere.
Apartment in Principina a Mare
5 out of 5 average rating, 6 reviews

Romantico Monolocale con vista sul Parco

ClaudiaRating, 5 stars4 days ago
siamo stati una settimana mio marito ed io e ci siamo trovati benissimo. la zona è tranquilla, ottima per riposare , ed è vicina alla spiaggia. alloggio pulito e con tutto ciò che poteva servire. le ragazze sono state tutte sempre molto disponibili e accoglienti. lo consiglio a chi vuole godersi giorni per recuperare, senza il caos del turismo .
Superhost
A spacious room features a four-poster bed draped with light fabric. An inviting dining area includes a wooden table and chairs. Exposed wooden beams and stone walls create a rustic charm, while large windows offer natural light and views of the outside landscape.
Apartment in Monterotondo Marittimo
4.76 out of 5 average rating, 37 reviews

Studio in Farmhouse, Swimming Pool, Restaurant.

ElenaRating, 5 stars2 months ago
Wir hatten eine schöne Zeit mit leckerem Essen und sehr freundlichen Gastgebern. Die Lage war wunderschön und die Zeit sehr entspannend. Vielen Dank :)
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
4.93 out of 5 average rating, 137 reviews

Splendido fienile ristrutturato in Toscana

PhilippRating, 5 stars1 month ago
Wir hatten eine wunderschöne Woche in Glorias Haus. Unser vierbeiniger Freund hat sich in der Natur auch total wohl gefühlt. Das Haus ist klein aber fein und hat alles was man braucht. Das Grundstück hat eine schöne Größe und eignet sich perfekt um draußen zu Essen, im Whirlpool zu entspannen oder einfach in der Sonne zu liegen. Der Weg zum Haus ist ein wenig anspruchsvoll, aber mit einem normalen Auto und ein bisschen Fahrpraxis durchaus zu meistern. Gloria war für uns immer erreichbar und hat uns bereits im Vorfeld gute Ausflugstipps für die Gegend gegeben. Auch bei eventuellen Nachfragen hat sie immer sehr schnell reagiert und uns geholfen. Um einfach mal raus zu kommen und die Natur und die Ruhe der Toskana zu genießen, ist es perfekt. Wir kommen gerne wieder!
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

LéaRating, 5 stars6 days ago
Nous avons adoré notre séjour chez Bernardino ! Le paysage est magnifique, l’endroit est très propre et la piscine est un vrai plus pour se détendre. Bernardino est un hôte attentionné, toujours à l’écoute et prêt à aider à tout moment. Merci pour cette belle expérience !
Top guest favorite
A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.
Apartment in Siena
4.91 out of 5 average rating, 129 reviews

Villa’Colombaiolo di Marciano',28

EwaRating, 5 stars3 weeks ago
Wygodny choć nieco staromodny apartament w spokojnej okolicy, wokół dużo zieleni i piękny widok z okna. Duży i zadbany basen z przestrzenią do odpoczynku. Dobre miejsce na relaks po zwiedzaniu Sieny i okolic.
Guest favorite
A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.
Cottage in Seggiano
4.96 out of 5 average rating, 90 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

ChrisRating, 5 stars1 week ago
Third time at this beautiful place! As always a nice surprise
Top guest favorite
An elegantly furnished living room features classic decor, including a chandelier and ornate details. Large windows offer views of the city's architectural highlights. Comfortable seating arrangements, including a tufted sofa and armchairs, are arranged around a glass coffee table, enhancing the room's inviting ambiance.
Home in Siena
4.96 out of 5 average rating, 134 reviews

Domus Nannini - Loggia Salimbeni SPA

YingRating, 5 stars1 month ago
这是住过最好的最有特色的民宿,像宫殿一样的房间,四面墙加顶都是湿壁画,叹为观止,设施也非常齐全,最最关键是房东态度很好,入住时帮我们提东西,入住后一直在关心我们,给我们准备了很多水和零食,问候入住的体验感,告诉我们哪里吃东西比较方便也推荐了很多当地比较好的餐厅。强烈推荐!

Family- and pet-friendly home rentals

Guest favorite
A small harbor is visible, lined with numerous boats of various sizes. A stone wall borders the waterfront, complemented by a tower and colorful buildings in the background. The scene is illuminated by soft, golden light from the setting sun.
Apartment in Piombino
4.87 out of 5 average rating, 214 reviews

Accogliente appartamentino in centro storico

KateRating, 5 starstoday
What can I say! Daria had prepared the apartment for everything. We needed for our arrival, milk, tea, coffee, cleaning products, snacks, drinks. Having stayed in Tuscany for the last 25yrs these little touches are hard rare and so welcomed after a long day travelling. We really were blown away by the location and how perfect the apartment was for our stay! Everything from the cleanliness, responsiveness, Daria really couldn’t do enough for us. Don’t miss out on this amazing place! Daria, we can’t thank you enough!! Kate and Tammy xx
Guest favorite
The spacious living area is furnished with a blue sofa and a light armchair, complemented by decorative artwork on the walls. A glass coffee table displays colorful ornaments and a vase of flowers, adding a touch of warmth to the inviting space.
Condo in Castiglione della Pescaia
4.86 out of 5 average rating, 51 reviews

Appartamento a due passi dal mare

GlauciaRating, 5 stars1 month ago
Laura’s apartment is very cozy and well equipped, you can feel it is a family home. I enjoyed a lot staying there for 2 weeks, it is spacious, and close enough to walk everywhere , yet more secluded in a quieter area, with peace and silence.
Guest favorite
An open door reveals a scenic view of historic buildings on a hillside. Light floods the room, highlighting the wooden furniture and stone flooring. A subtle contrast between the interior and the vibrant landscape can be seen in the background.
Earthen home in Pitigliano
4.87 out of 5 average rating, 906 reviews

La grotta

SavannahRating, 5 stars1 week ago
One of the most unique, homey and wonderful places on earth. Found Pitigliano with a little research and glad we did - make sure you make your way to Saturnia for the thermal pools as well. Was a little caught off guard with no WiFi for international travel but had WiFi at the cafe upstairs!
Guest favorite
A spacious living area features a green-patterned couch and a wooden coffee table. Natural light enters through large windows, illuminating the stone wall and wooden beams above. An open kitchen is equipped with appliances, while a dining area is visible in the background.
Condo in Castiglione della Pescaia
4.88 out of 5 average rating, 99 reviews

Little Jewel in the center of CDP

NadiRating, 5 stars3 weeks ago
We loved the apartment. It was cozy, well equipped and had everything one might need. It is extremely central and you can walk everywhere. Parking is very close. Ingrid was very helpful and gave us tips and suggestions for our stay. All in all a wonderful stay.
Guest favorite
The illuminated village of Pitigliano is captured at dusk, showcasing its distinct stone buildings and rooftops. The historic tower stands prominently in the background, while soft lights line the streets, creating a serene atmosphere in the valley below.
Apartment in Pitigliano
4.94 out of 5 average rating, 418 reviews

Attico panoramico nell'antico borgo

BrittanyRating, 5 stars1 week ago
Loved our stay! Great set up, great location, and really responsive host. Check in was easy, we had everything we needed and the views are INCREDIBLE from the house. There’s also a nice coffee place just downstairs that opens early. Highly recommended!
Guest favorite
A panoramic view of the sea is visible, featuring various boats navigating through the calm waters. The shoreline is lined with charming buildings, enhancing the coastal landscape. A clear sky and distant mountains can be observed in the background.
Apartment in Porto Santo Stefano
4.88 out of 5 average rating, 772 reviews

CASA VISTA MARE:CONSEGNA CHIAVI O SELF CHECK IN

MarcoRating, 5 stars1 day ago
…più di quanto ci si aspetta! Entrare in casa di Sonia è come essere in vacanza dai genitori: ogni accortezza è presente. Meglio di quanto descritto sulla presentazione Airbnb.
Top guest favorite
A well-lit living area features a large world map on the wall, alongside a white shelving unit filled with books. A television sits on a white cabinet. A wooden dining table is accompanied by several chairs, set against the backdrop of a bright, airy space.
Condo in Castiglione della Pescaia
5 out of 5 average rating, 69 reviews

Sea House

MichalRating, 5 stars2 weeks ago
I recently had the pleasure of staying at Consuelo's Airbnb apartment near the sea in Castiglione de la Pescaia, and it was an exceptional experience from start to finish. Consuelo is an outstanding host—both incredibly helpful and remarkably responsive. From the moment I booked, she ensured smooth communication, promptly addressing any queries I had with warmth and efficiency. Her attention to detail and dedication to guest comfort made our stay truly effortless. The apartment itself was spotless, well-equipped, and perfectly situated for easy access to the beautiful coastline. I wholeheartedly recommend Consuelo's Airbnb to anyone looking for a delightful seaside retreat. Her hospitality truly elevates the experience, making it feel like a home away from home.
Guest favorite
A charming villa is nestled amidst a lush green lawn, framed by flowering trees. Blue-shuttered windows and a terracotta roof feature prominently, complemented by a stone chimney. The surrounding landscape creates a serene outdoor setting perfect for relaxation.
Villa in Castagneto Carducci
4.94 out of 5 average rating, 121 reviews

La Conchetta - Bolgheri

JanRating, 5 stars1 month ago
Wir waren jetzt zum zweiten Mal hier und wir sind wieder begeistert. Wir lieben das Haus und die Umgebung ist für uns perfekt. Gerne wieder :-)

Family-friendly home rentals with a pool

Top guest favorite
A natural pool is set amidst a garden-park featuring various trees, including ancient cypress. The pool reflects the clear blue sky, while gravel pathways surround it, creating a serene outdoor space. Verdant greenery provides a backdrop to this tranquil setting.
Apartment in Montalcino
4.9 out of 5 average rating, 359 reviews

Panoramic Country Suite Montalcino

BernhardRating, 5 stars4 days ago
Wir waren eine Woche bei Aleksandra in Montalcino im Herzen des Brunello, eine atemberaubend schöne Gegend. Das grosse Anwesen ist traumhaft und mit der Ruhe und dem Ausblick genau das richtige um zu entspannen und die Seele baumeln zu lassen. Ein unvergessliches Erlebnis für die ganze Familie. So stellt man sich einen Toskanaurlaub vor. Wir können die Unterkunft wärmstens empfehlen.
Superhost
Apartment in San Gimignano
4.87 out of 5 average rating, 157 reviews

Apartment Melogranowith great views

KoenRating, 5 stars3 days ago
We zijn 5 nachten op dit prachtige adres geweest. Heel dicht bij San Gimignano maar toch met een rustige ligging. Prachtig uitzicht op het Toscaanse landschap én op San Gimignano. De ruimte was erg netjes en schoon, in het echt was het nog beter dan op de foto’s. Roberto en zijn vrouw waren erg vriendelijk en behulpzaam en onderhouden de locatie en de tuin erg goed. We hebben een top verblijf gehad en hopen hier eens terug te komen!
Guest favorite
A refreshing swimming pool is surrounded by lush greenery and sun loungers. Colorful umbrellas provide shade, enhancing the outdoor relaxation area. In the background, the rustic stone farmhouse is visible among the trees, complementing the tranquil setting.
Apartment in Casole D'Elsa
4.93 out of 5 average rating, 104 reviews

Girasoli appartamento con piscina in agriturismo

CedricRating, 5 stars2 days ago
Wir waren begeistert von Manuela und Massimos Unterkunft, welche in einer sehr guten Lage nähe Casole d'Elsa in der wunderschönen Toskana liegt. Es war wie im Bilderbuch! Die Wohnung war super sauber und gut eingerichtet. Manuela war stets hilfsbereit und hat bei Fragen in wenigen Minuten geantwortet und sehr gute Tipps gegeben. Der hauseigene Pool war bei den Temperaturen besonders erfrischend und wurde jeden Morgen, selbst am Wochenende, von Massimo sehr sauber gemacht. Besonders aufmerksam fanden wir die Geschenke von den beiden. Sei es selbst hergestelltes Öl, Untersetzer oder einen leckeren Wein. Wir würden jederzeit wiederkommen.
Guest favorite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle
4.97 out of 5 average rating, 193 reviews

Stone House with Exclusive Pool Codilungo in Chianti

SarahRating, 5 stars2 weeks ago
We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!
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 stars2 weeks 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.
Superhost
A large swimming pool is surrounded by sun loungers and umbrellas, set against a backdrop of lush hills and rustic buildings. The clear blue water reflects the sky, while the terracotta-colored structure in the distance retains its traditional charm.
Farm stay in Provincia di Siena
4.87 out of 5 average rating, 118 reviews

Spigo - Indipendent Cottage Zampugna

FilipRating, 5 stars6 days ago
Nádherné místo, vše připraveno i s občerstvením, ubytování klidné a čisté ... Klimatizace funkční, ale skoro nebyla potřeba, protože to bylo krásné klasické toskánské ubytování, kde jsme rozhodně nebyli naposledy
Guest favorite
A serene stone pool reflects the clear sky, set against a backdrop of lush trees and rolling hills. The inviting water is framed by a stone deck, with a single umbrella providing shade nearby. The tranquil landscape offers a peaceful escape.
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Casa Vecchia

LucyRating, 5 stars2 weeks ago
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)
Guest favorite
A refreshing swimming pool is surrounded by lounge chairs and umbrellas, creating a relaxing outdoor space. Lush greenery and flowering plants add color to the area. Rustic stone buildings are visible in the background under a clear blue sky.
Vacation home in Sovicille
4.93 out of 5 average rating, 107 reviews

Podere La Castellina - N°2 LECCETO

SophieRating, 5 stars2 weeks ago
Wir hatten einen tollen Aufenthalt! Simona hat uns direkt herzlich empfangen und uns alles in Ruhe gezeigt. Das Airbnb liegt wunderschön inmitten der Natur – perfekt, um abzuschalten und zur Ruhe zu kommen. Die Unterkunft war sehr sauber, liebevoll und gemütlich eingerichtet. Wir haben uns rundum wohlgefühlt und würden jederzeit wiederkommen. Vielen Dank für die schöne Zeit!

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

  • Total rentals

    230 properties

  • Nightly prices starting at

    G$8,363 GYD 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

Destinations to explore