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Family-friendly holiday rentals in Castiglioncello

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Castiglioncello

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A living area is presented with a blue sofa adorned with decorative cushions. Adjacent to it, an antique wooden wardrobe complements the space. A colorful rug is laid on the tiled floor, while a large painting hangs above the sofa, adding an artistic touch. Natural light enters through the windows.
Flat in Lucca
5 out of 5 average rating, 141 reviews

MADONNA DELLO STELLARIO by Vivy HISTORICAL CENTER

The apartment is in the heart of the historic center in the ZTL area, in Piazza San Francesco in front of the Madonna dello Stellario column, a few meters from Via Fillungo and the Cathedral, close to restaurants, wine bars and slow food. Overlooking Via del Fosso with a characteristic terrace, it was completely renovated at the end of 2018, maintaining its ancient Lucchese structure but providing it with all modern comforts: Wi-Fi, air-conditioning, washing machine, equipped kitchen and smart TV

Guest favourite
A stone cottage is nestled among trees, creating a natural boundary for the property. Soft nighttime lighting highlights the textured facade, while glimpses of a salt-water pool and landscaped garden are visible in the background, suggesting a tranquil outdoor area.
Loft in Rosignano Marittimo
4.94 out of 5 average rating, 142 reviews

Il Cubetto - Sun Studio: absolute exclusivity

Our little place, Il Cubetto, inaugurated with the 2020 season, stands in full Tuscan country and is particularly distinctive because of its absolute exclusivity: only two studio apartments within our 7000 sqm of garden planted with many fruit trees, with great attention to any detail. Our guests, a maximum of two per studio apartment, have the use of a salt-water infinity swimming pool overlooking the valley. Depending on the car they drive, they can park next to the cottage or beside the road.

Top guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home in Peccioli
4.99 out of 5 average rating, 135 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Top guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.95 out of 5 average rating, 126 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Superhost
A rustic stone building features a charming entrance adorned with blooming flowers and lush greenery. The structure showcases traditional architecture with arched doorways and a tiled roof, set against a clear blue sky and surrounded by serene natural beauty.
Holiday home in Casole d'Elsa (SI)
4.91 out of 5 average rating, 218 reviews

Charming farmhouse with garden, views & pool

Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. The stone farmhouse has been restored over the years to create 3 totally separate apartments, each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and magnificent sunsets. It is a calm, relaxed place, an idyllic retreat away from the crowds ideal for couples.

Guest favourite
A bright living area features a comfortable sofa and a modern entertainment unit with a flat-screen TV. A dining table for six is present, accompanied by several chairs. Natural light filters in through the sliding glass doors that lead to a balcony.
Flat in Rosignano Solvay
5 out of 5 average rating, 13 reviews

A stone's throw from the sea

A 50 metri dal mare con vista – Ideale per famiglie Luminoso e spazioso appartamento situato a soli 50 metri dal mare, nella rinomata zona del Porto Turistico Cala de’ Medici a Rosignano Solvay. La casa è perfetta per famiglie o piccoli gruppi fino a 5 persone che desiderano una vacanza rilassante vicino alla spiaggia. L’alloggio offre ambienti ampi e ben arieggiati, con due balconi vista mare dove potersi godere la brezza marina.

Top guest favourite
The entrance to the apartment features a wooden door framed by flowering plants in pots. A well-maintained tiled area serves as a welcoming threshold, with sunlight creating soft shadows on the pink exterior wall.
Apartment in Rosignano Marittimo
4.97 out of 5 average rating, 31 reviews

My Pink House

The apartment is in a very quiet area of Rosignano Marittimo, a small hill town not far from the Etruscan Coast and the sea (about 5 km). It is very easily reachable thanks to the main roads such as the Tyrrhenian Highway and the Aurelia Variant, thanks to which you can also very easily visit the main Art Cities of Tuscany, the typical Villages or you can very simply enjoy the sea and return in the evening feeling at home.

Top guest favourite
A welcoming living area features a light-colored sofa set arranged around a small coffee table. Natural light enters through a doorway, illuminating the space. A potted plant adds a touch of greenery, and a staircase leads to the upper floor.
Flat in Rosignano Solvay-Castiglioncello
4.98 out of 5 average rating, 130 reviews

Casa Gianguia apartment 100 meters from the sea

Villa such as "viareggina", called "Gianguia", located in an excellent location with respect to the center of Castiglioncello and Rosignano, a short walk from the sea, and the main services. Recently renovated, with practical and modern furnishings but tasteful ; equipped with all the comforts to ensure guests a pleasant and relaxing stay. Great for couples and families who love the sea and relaxation.

Guest favourite
A sunlit corner captures a stunning ocean view during sunset. Large glass windows frame the horizon, reflecting vibrant orange and pink hues over the water. A potted plant adds greenery to the space, set against a backdrop of navy blue tiles and soft, flowing curtains.
Flat in Castiglioncello
5 out of 5 average rating, 6 reviews

Belvedereloft il mare sotto casa con scesa al mare

Belvedereloft overlooks the beautiful Bay of Quercetano in Castiglioncello, a special location that makes it unique for its breathtaking view. It is part of a property whose access, that is, the gate, is the private descent to the beach, are shared with the owners, the terraces are exclusively for the guests, but the owners can pass through. Only for adults

Top guest favourite
A well-lit kitchen features a circular wooden dining table surrounded by chairs. Green cabinets complement the pink and white hexagonal floor tiles. A large window allows natural light to flood the space, highlighting the vintage kitchen appliances and decorative items on the counter.
Flat in Rosignano Solvay-Castiglioncello
5 out of 5 average rating, 13 reviews

Fattoria Beletage with rooftop terrace & pool

The Beletage apartment on the first floor of the Fattoria Le Case Nuove is a gem that was reserved for the family until recently and is now offered for rent after a renovation. Once the preferred residence of the Conti Millo family, the Beletage with its roof terrace and stunning views over the pine tops to the sea is the jewel of the estate.

Top guest favourite
An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.
Farm stay in Palaia
4.98 out of 5 average rating, 179 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Guest favourite
A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.
Apartment in San Gimignano
4.95 out of 5 average rating, 139 reviews

Adalberto Apartment inside the Manor of Fulignano

Nella campagna di San Gimignano, in antica fortificazione risalente all'anno 1000 ora dimora di campagna, situata su di un colle con veduta panoramica, affittasi bellissimo appartamento di ca. 60mq con vista su San Gimignano e sui vigneti circostanti

Popular amenities for Castiglioncello family-friendly rentals

When is the best time to visit Castiglioncello?

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Avg. price$150 SGD$153 SGD$174 SGD$143 SGD$149 SGD$154 SGD$219 SGD$219 SGD$178 SGD$168 SGD$220 SGD$223 SGD
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Quick stats about holiday rentals that are family-friendly in Castiglioncello

  • Total holiday rentals

    Explore 120 holiday rentals in Castiglioncello

  • Nightly prices starting at

    Castiglioncello holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,480 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    80 of Castiglioncello holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castiglioncello rentals

  • 4.7 Average rating

    Castiglioncello stays receive an average rating of 4.7 out of 5 from guests