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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
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Apartment
5 out of 5 average rating, 202 reviews

Ancient 17th-century farm in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional style of ancient Tuscany: wooden beams, terracotta floors, and tasteful handcrafted furnishings that will help you enjoy a pleasant stay. In the large outdoor courtyard, you'll find a saltwater swimming pool on a panoramic terrace with wonderful views of the castle, hills and vineyards, and breathtaking sunsets.

Guest favourite
A light and airy dining area features a circular table surrounded by white chairs and stools. A small decorative table holds a dried floral arrangement. Vintage-style wall art and a map are displayed, adding character to the space.
Loft
4.91 out of 5 average rating, 32 reviews

Casina del Sorriso

Ideal for enjoying the sea of Castiglioncello just 200 meters away. The Casina del Sorriso offers Wi-Fi, a smart TV, air conditioning, a private parking space, a small garden, an outdoor shower, linen, taxes and utilities included, and 2 bicycles to use to explore the town and its surroundings. Perfect for a single traveler or a couple (max 4 people) thanks to the privileged location you will have the opportunity to savor the beauty of Castiglioncello. 20 minutes from Casale Marittimo, Bolgheri, Livorno.

Superhost
The kitchen area features modern cabinetry and appliances, including a refrigerator and stove. A dining table is set for four, complemented by metal chairs. Natural light enters through a nearby window, while decorative artwork adds a touch of color to the neutral-toned walls.
Flat
5 out of 5 average rating, 9 reviews

Monte alla Rena - Two-room apartment with garden 200m from the sea

Nice two-room apartment on the ground floor, completely renovated, with a private garden equipped with all comforts. 200 meters from the sea, 100 meters from neighborhood shops (grocery stores, pharmacy, etc.). A few kilometers away from Vada (with its wide beaches of light sand) and Castiglioncello (the Pearl of the Tyrrhenian Sea) easily accessible by bus or private transport. In the central area, from which you can easily reach the main Tuscan cities: Livorno, Pisa, Florence, Elba Island.

Top guest favourite
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
4.93 out of 5 average rating, 195 reviews

Collina Power

Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.

Top guest favourite
The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.
Home
4.99 out of 5 average rating, 275 reviews

Tuscan cottages in an ancient villa with a garden

The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

Guest favourite
Flat
5 out of 5 average rating, 5 reviews

Historic fattoria with pool

The property is about 1 km from the sea (only 8-10 minutes' walk) and has about 150 hectares of land in the hinterland with grain fields, maquis and olive trees as well as a small lake. The Fattoria with about 150 square meters of living space was built around 1800 and has since served the family as a summer and country residence. At the front is a classic garden. The 6 x 20 meter pool is also used by 2 other guest families, but offers enough retreat options due to the spacious complex.

Guest favourite
The image displays a satellite view of a coastal area, highlighting the proximity to the sea and surrounding amenities. A circular inset features a view of a walkway, complemented by a bright sky. Nearby, buildings and parking spaces are visible, indicating accessibility to local attractions.
Apartment
4.92 out of 5 average rating, 26 reviews

“Charming stay by the sea”

Bellissimo appartamento, con parcheggio pubblico gratuito, direttamente sul Lungomare di Crepatura, con le sue incredibili insenature naturali, le spiagge e l'acqua cristallina. L'alloggio è totalmente rinnovato ed è dotato di aria condizionata, cassaforte, zanzariere e lavatrice. A pochi passi sono presenti ristoranti, pizzerie, un supermercato e una farmacia. E' il posto perfetto per visitare le bellissime spiagge della zona, Bolgheri, e tutti i borghi della Costa degli Etruschi.

Guest favourite
Holiday home
4.89 out of 5 average rating, 18 reviews

casa la dori

Vacation home located 200 meters from the sea in a central area very well served by neighborhood shops. Raised ground floor, with a private garden where you can have lunch, dinner or simply rest in the cool of a pleasant sea breeze. Completely renovated, refurbished and cared for in every detail, it has a very large and elegant living area with a large window that allows access to the garden. New kitchen equipped with dishwasher, two bedrooms and a fully renovated bathroom.

Top guest favourite
The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.
Farm stay
4.91 out of 5 average rating, 268 reviews

Casa al Gianni - Fig

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

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
4.99 out of 5 average rating, 140 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
4.95 out of 5 average rating, 133 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.

Guest favourite
The kitchen area features a round wooden dining table set for six, complete with light blue plates and glassware. Modern appliances are integrated into the sleek cabinetry, and a cozy corner displays a minimalist TV above the counter. An archway leads to another room.
Home
5 out of 5 average rating, 10 reviews

[LUXURY]Exclusive apartment between downtown and the sea

New, exclusive luxury home in Castiglioncello’s main square, 500m from the sea and 1.5 km from Cala ’de Medici port. Parking included. Beach service available on request: assistance with reservations, subject to availability. Modern, refined design with elegant arched doors and wood details. Unique, sophisticated atmosphere for a 5-star stay! Perfect location, walking distance to all services, ideal for leaving the car behind and exploring on foot.

Popular amenities for Castiglioncello family-friendly rentals

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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 £15 per night before taxes and fees

  • Verified guest reviews

    Over 1,430 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    90 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