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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 spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.
Cottage in Sovicille
4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

LesleyRating, 5 stars8 months ago
Lovely, peaceful, spacious place with a kind and generous host in Simone. He met us as we arrived and used his wagon to help move our luggage into the cottage. Big rooms, lots of space, many handy supplies in the kitchen. Good shower, comfortable bed. Enough bench space in the bathroom to put your things. Simone was really helpful with local recommendations for restaurants and where to park the car. One day he made a delicious tart and bought us in half. Would recommend staying at his place.
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
We had a lovely time with delicious food and very friendly hosts. The location was beautiful and the time very relaxing. Thank you :)
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

Beautiful renovated barn in Tuscany

PhilippRating, 5 stars4 weeks ago
We had a wonderful week in Gloria's house. Our four-legged friend also felt totally comfortable in nature. The house is small but nice and has everything you need. The property is a nice size and is perfect for eating outside, relaxing in the hot tub or just lying in the sun. The way to the house is a little challenging, but with a normal car and a little driving experience it can be mastered. Gloria was always available to us and gave us good excursion tips for the area in advance. Even with any inquiries, she always responded very quickly and helped us. To just get out and enjoy the nature and tranquility of Tuscany, it is perfect. We will be happy to come back!
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 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, 159 reviews

Country house La Meria

AlexRating, 5 stars2 months ago
If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!
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

HannahRating, 5 stars3 weeks ago
We loved staying here and had the most fantastic time. They were super helpful and responsive to everything and we can’t wait to go back.
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 – modern design in quiet panoramic location

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

DavidRating, 5 stars2 weeks ago
Great central location. Close to everything. Space is spread out so your tripping over your other guests

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, 213 reviews

Cozy apartment in the historic center

Rating, 5 stars6 days ago
I like this apartment very much, it’s in the Main Street. The only problem is shower room is bit too small. And Daria is a very friendly person.
Superhost
A spacious living area features a contemporary design with light hardwood floors. A large wall-mounted television is positioned above a sleek wooden console. The open-concept kitchen showcases modern appliances and a peninsula with seating, while colorful light fixtures add a playful touch.
Apartment in Castiglione della Pescaia
4.81 out of 5 average rating, 27 reviews

Dimora Pascoli 1

GiusyRating, 5 stars10 months ago
Apartment 100% as described. We were pleasantly surprised: the apartment is definitely spacious, fresh and equipped with every comfort. The furniture is very modern. Impeccably clean. The location is strategic: in less than a minute on foot you can find yourself in the main street of the center of Castiglione with numerous shops and restaurants (a tip: always book for time because you risk staying without dinner! We were in Castiglione in the week of August and without booking it was difficult to find a place even late in the evening). In a few minutes by foot you can find yourself on the waterfront where there are many beach establishments but also numerous free beaches. Right outside the apartment, the supermarket is very comfortable! Niccolò and Daniela were always kind and super helpful: we especially thank Daniela for all the tips she gave us!!!! Not recommended!
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

Apartment within walking distance of the sea

GlauciaRating, 5 stars4 weeks 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.
Superhost
An arched stone doorway opens to a scenic view of the sea, framed by rugged walls covered in greenery. The pathway is lined with stones, leading to an elevated area where a bench is situated, offering a spot to enjoy the coastal landscape.
Home in Castiglione della Pescaia
4.69 out of 5 average rating, 62 reviews

Le Rocchette – Castiglione della Pescaia – Maremma

LeonardoRating, 5 stars9 months ago
Everything as expected: great location, spacious apartment for couples, very nice hosts, we will definitely be back.
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.
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
We were here for the second time and we are thrilled again. We love the house and the surroundings are perfect for us. We'd love to come back :-)
Superhost
A serene bedroom is featured, highlighting a spacious bed with a blue coverlet. Above the bed, a quote is displayed on the wall, emphasizing inspiration. A soft light fixture hangs from the ceiling, and a bedside table with a lamp is positioned within the room.
Apartment in Castiglione della Pescaia
4.73 out of 5 average rating, 85 reviews

Three-room apartment and parking just a short walk from the center and the sea

MarilenaRating, 5 stars1 month ago
It was a very pleasant stay, perfect home, functional for all needs. Great location, in a quiet place and within walking distance of the historic center. Very convenient indoor parking spot. Livia is a super available host :)

Family-friendly home rentals with a pool

Top guest favorite
A hammock is gently suspended between wooden posts, surrounded by a lush green lawn and trees. Colorful flower pots are positioned nearby, and charming rustic buildings are visible in the background under a clear blue sky.
Farm stay in Magliano in Toscana
5 out of 5 average rating, 31 reviews

agriturismo Torribasse

SophieRating, 5 stars9 months ago
The property is very nicely located in the middle of the countryside, the sea can be reached in about 20 minutes by car. Enrico gives many tips for excursions and activities nearby upon arrival. The place itself was clean and well equipped, you have everything you need.
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, 103 reviews

Girasoli apartment with pool in farmhouse

RichardRating, 5 stars1 month ago
Beautiful rustic stay in the heart of Tuscany. Manuela was very friendly and helpful. The farm at night with the fireflies lighting up the bushes and nightingale singing in the trees was absolutely enchanting.
Superhost
Villa in Seggiano
5 out of 5 average rating, 8 reviews

Case Bianchi

JulianeRating, 5 stars3 weeks ago
We had a great time! Super clean and spacious house with a nice outdoor area. Constanze was always super helpful and responded quickly. But be aware, you need a car and restaurants and supermarkets are not in walking distance. Thanks a lot for having us.
Guest favorite
A shared outdoor pool is surrounded by a well-maintained garden, featuring several lounge chairs in blue fabric. A small table is set nearby, creating a relaxing space to enjoy the warm sun and greenery. Lush plants and trees complement the tranquil setting.
Apartment in Castiglione della Pescaia
4.88 out of 5 average rating, 25 reviews

Agriturismo Bandinelli #1 "Rotana"

DominikRating, 5 stars8 months ago
Wonderful stay at an authentic Tuscan farmhouse! We found exactly what we were looking for: a classic old farmhouse that perfectly reflects the atmosphere of Tuscany. The spacious garden and peaceful surroundings allowed us to fully relax and unwind. The rooms are beautifully decorated with great attention to detail – perfect for winding down after a long day. The rooms are a bit noisy, but it wasn't a major issue for us. Communication with David was excellent and straightforward. Hopefully, this won't be our last stay here!
Guest favorite
A private pool area is surrounded by lush green grass and lounge chairs. Shade is provided by large umbrellas. In the background, rolling hills dotted with vineyards and distant buildings create a serene countryside landscape under a partly cloudy sky.
Apartment in San Gimignano
4.89 out of 5 average rating, 126 reviews

Apartment Ortensia

DanielaRating, 5 stars2 months ago
Great place! We loved it!
Guest favorite
A tranquil pool area is surrounded by greenery and trees, enhancing a sense of privacy. Loungers are positioned nearby on a stone terrace, with a landscaped garden featuring aromatic plants providing a natural border. The clear water invites relaxation in a peaceful outdoor space.
Vacation home in Casole d'Elsa (SI)
4.91 out of 5 average rating, 205 reviews

Charming farmhouse with garden, views & pool

DylanRating, 5 stars3 weeks ago
My stay at Fabio’s farmhouse was delightful. The house was gorgeous and felt right at home. The house felt cozy and comfortable with breathtaking views of the Tuscany country side. The area is very serene and peaceful. There are plenty of beautiful villages around the area to visit via car. Fabio was a delightful host who was very welcoming and responsive. I am looking forward to staying again here in the future.
Guest favorite
Apartment in Carpineto
4.95 out of 5 average rating, 171 reviews

Tuscan countryside, peace and relaxation 10 minutes from Siena

NoahRating, 5 stars1 week ago
Beautiful place near Siena. The hosts are very friendly and kind. We really enjoyed our stay in here!
Top guest favorite
Villa in San Leolino
4.99 out of 5 average rating, 110 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

TjadeRating, 5 stars2 days ago
We had a wonderful time in this beautiful house – everything was very clean, lovingly decorated and well equipped. Even with our dog, we felt completely comfortable, it was absolutely dog-friendly! The hosts were incredibly warm and helpful – they immediately felt welcome. A special highlight was the pizza evening offered – it was not only super cozy, but also a real culinary experience. Honestly, one of the best pizzas I've ever eaten! We'd love to come back – absolute recommendation! 🌟

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

  • Total rentals

    230 properties

  • Nightly prices starting at

    G$8,368 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

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