Some info has been automatically translated. Show original language

Family-friendly holiday rentals in Castiglione della Pescaia

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 270 holiday rentals in Castiglione della Pescaia

  • Nightly prices starting at

    Castiglione della Pescaia holiday rentals start at $102 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,510 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    170 of Castiglione della Pescaia holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castiglione della Pescaia rentals

  • 4.7 Average rating

    Castiglione della Pescaia stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Castiglione della Pescaia

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

1 of 1 pages1 / 1
Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 283 reviews

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Top guest favourite
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, 154 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favourite
A panoramic terrace is visible, featuring a small table set with a light purple tablecloth and dark chairs. The surrounding stone wall offers views of the landscape at sunset, highlighting rolling hills and distant towers.
Tower in San Gimignano
4.95 out of 5 average rating, 129 reviews

Medieval Tower experience with Panoramic Rooftop

If you are looking for a unique experience in the heart of San Gimignano, this is the place for you. With its 42 mt of height, Torre Salvucci Maggiore is one of the medieval town's famous towers and today the only one turned into a vertically-spread accommodation divided into 11 floors for a total of 143 steps. A magical setting unlike any other. The tower can hosts couples or small groups of up to 3 people. At the top, the panoramic terrace awaits for you with an axtraordinary 360° city view.

Top guest favourite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5.0 out of 5 average rating, 113 reviews

Captain's House | Monte Grosso, Elba

The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Guest favourite
A bright and airy dining area features a small table surrounded by four chairs. Natural light enters through two large windows, with scenic views visible outside. A kitchenette is situated nearby, equipped with modern cabinetry and appliances, providing convenience for meal preparation.
Apartment in Castiglione della Pescaia
4.97 out of 5 average rating, 31 reviews

The most beautiful apartment in front of the sea

Come see this beautiful and exclusive 5 beds 2 bath seaside. This home features all New recently. Kitchen has Newer Appliances and Cabinets. Spacious light Living Room with 4 windows. Master Suite leads to a private bathroom. Updated Master Bath features Walk-in Shower. All rooms are equipped with TV and air conditioning. High speed WiFi included. City Center, Shopping are close by and easy access by feet or bike. Sailing and Kitesurfing available nearby. Animals and smoking not allowed.

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 137 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favourite
A yurt is shown at night, illuminated warmly from within. The starry sky features the Milky Way, providing a stunning backdrop. An outdoor seating area with a thatched roof is visible, showcasing a tranquil atmosphere amidst a natural landscape.
Yurt in Asciano
4.98 out of 5 average rating, 195 reviews

2 ❤️ and 1 Yurt Glamping in Tuscany for adults only

Romantic glamping for adults, in the heart of the Tuscan countryside. Silver 35 m² yurt tent + 7 m² private en-suite bathroom + private outdoor wood-fired hot tub* (*EXTRA CHARGE), private relaxation veranda. Heating in the winter and air conditioning in the summer. Dinners with delivery directly to the Yurt, available for an even tastier experience (*SURCHARGE*). - Private parking, WiFi - Kitchen with refrigerator, microwave, (NO STOVE) + private outdoor barbecue.

Guest favourite
A charming stone cottage is depicted, featuring a dark roof and a welcoming entrance. Vibrant purple flowers in the foreground provide a splash of color against the gravel pathway, while warm sunlight casts a gentle glow, highlighting the serene surroundings.
Flat in Castiglione della Pescaia
4.95 out of 5 average rating, 141 reviews

Casetta Venere Tuscan relaxation 3 km from the sea

Casetta Venere: Sea, nature and Pet-Friendly. Just 3 km from the crystal clear sea of Castiglione della Pescaia, Casetta Venere is a small Tuscan jewel among olive trees, perfect for couples, families, and travelers with pets. The house offers well-kept spaces, a beautiful private garden and an intimate and welcoming atmosphere. We look forward to welcoming you for a slow, authentic and beautiful stay in the midst of nature.

Guest favourite
Dome in Volterra
4.96 out of 5 average rating, 150 reviews

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Guest favourite
A view from the entrance, featuring a gate leading to a sandy beach. Flanking the pathway are greenery and trees, while the ocean can be seen in the distance under a clear blue sky. The scene captures a peaceful coastal atmosphere.
Apartment in Castiglione della Pescaia
4.83 out of 5 average rating, 113 reviews

Beach apartment with private parking space

From the living room to the beach in a leap. From the window overlooking the pedestrian promenade, you can immerse yourself in the sound of the waves while watching the sunset over the Tyrrhenian Sea. In the private back garden, you can spend unforgettable evenings away from prying eyes, perhaps with a nice candlelit dinner, enjoying the scents of wild Maremma nature.

Top guest favourite
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.
Apartment in Castiglione della Pescaia
4.88 out of 5 average rating, 110 reviews

Little Jewel in the center of CDP

Typical bi-level studio right in the center of Castiglione della Pescaia with all the facilities at hand (restaurants, bars, shops, gelaterie, pharmacy ..) With stone walls, terracotta floors, beamed ceiling, wooden mezzanine and finishes, it has the typical tuscan atmosphere! Only 5 minutes walking distance from the sea

Top guest favourite
A solitary tree stands prominently in the foreground, framed against a vast landscape. Below, the coastline stretches toward the horizon, with the sea shimmering in the distance. The view includes a charming town nestled among the lush greenery of the surrounding hills.
Villa in Castagneto Carducci
4.99 out of 5 average rating, 122 reviews

sea view villa with private infinity pool

RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Popular amenities for Castiglione della Pescaia family-friendly rentals

When is the best time to visit Castiglione della Pescaia?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$212 SGD$200 SGD$186 SGD$177 SGD$182 SGD$204 SGD$252 SGD$283 SGD$187 SGD$173 SGD$209 SGD$224 SGD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°C