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

Top-rated family-friendly rentals in Castiglione della Pescaia

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

%{current} / %{total}1 / 1
Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 110 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top Guest favourite
Apartment in Caminino
4.91 out of 5 average rating, 184 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top Guest favourite
Cottage in Monteriggioni
4.95 out of 5 average rating, 269 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top Guest favourite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay in Seggiano
4.99 out of 5 average rating, 267 reviews

Terra Delle Sidhe, Seggiano, Tuscany, Italy

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Top Guest favourite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Condo in Asciano
4.97 out of 5 average rating, 321 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

Top Guest favourite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Apartment in Montemassi
4.97 out of 5 average rating, 116 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Guest favourite
A serene garden area features two lounge chairs positioned on lush green grass, overlooking the sea in the distance. White lilies bloom in the foreground, complemented by a rustic shade structure nearby, providing a tranquil setting for relaxation.
Farm stay in Castagneto Carducci
4.95 out of 5 average rating, 149 reviews

Casa del Poggio, with a beautiful sea view

The Casa del Poggio (house at the hill) is located in the hills of Castagneto Carducci and is part of our organic farm. It is immersed in a peaceful countryside surrounded by olive groves, vineyards and woodland and enjoys a beautiful view of the sea and the castle of Castagneto Carducci. At the same time its position allows you to reach the village in just 10 minutes by foot and the beaches of Marina di Castagneto in 10 minutes by car or bus.

Guest favourite
An aerial view captures the expansive countryside, characterized by lush greenery and rolling hills. The property features stone buildings nestled among trees, with a swimming pool visible in the foreground and fields stretching into the distance, offering a serene landscape.
Farm stay in Sovicille
4.95 out of 5 average rating, 128 reviews

Agriturismo La Villa - Il Ciliegio, Pool & Garden.

We are pleased to welcome you to our Cherry Tree House, the last newly renovated jewel of the Agriturismo La Villa. Located on second floor, built among the rocks of the typical Senese countryside, our new home will be ready to lull you into all kinds of comforts: free wifi, swimming pool, barbecue area, air conditioning, smart TV. private parking, wood and private garden, just 40 steps away, overlooking our lavender and olive grove.

Top Guest favourite
A ceramic vase filled with vibrant yellow flowers is prominently displayed on a table. Soft light from a lamp illuminates the rustic stone wall in the background, enhancing the warm ambiance of the space. Two mugs sit beside the vase, adding a touch of comfort.
Apartment in Scarlino
4.92 out of 5 average rating, 111 reviews

Leo's porch

Stay in this unique place and spend unforgettable evenings gazing at the horizon. Breathe clean air and enjoy the relaxation offered by the village of Scarlino. Ideal for couples or small families who want functional and comfortable accommodation. FROM MAY 1 TO AUGUST 31, a tourist tax of €1.00 per night/person is applied for each day of stay. Bed linen and towels are NOT INCLUDED in the final price of the accommodation.

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.
Apartment in Castiglione della Pescaia
4.96 out of 5 average rating, 102 reviews

Casetta Venere relaxing Tuscan 3 km from the sea

Venus cottage: 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 animals. The house offers curated spaces, a beautiful private garden, and an intimate and welcoming atmosphere. We are waiting for you for a slow, authentic and beautiful stay in the middle of nature.

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
4.91 out of 5 average rating, 240 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top Guest favourite
A light-filled living area features large glass windows, offering views of the surrounding nature. An orange armchair and a minimal dining table are visible, complemented by wooden cabinetry and kitchen appliances. Natural light illuminates the space, enhancing the warm tones of the decor.
Home in Marrucheti
4.98 out of 5 average rating, 162 reviews

La Stallina - Perfect retreat from the city rush

Recently restored, La Stallina, was my grandfather's horse stable at the beginning of last century. Now it is a charming apartment perfect for a couple and suitable for 2+2 guests. One living room with kitchen in a conservatory, double bed and mezzanine with bed. Bathroom with large shower box, kitchen equipped with dish-washing and oven.

Popular amenities for Castiglione della Pescaia family-friendly rentals

When is the best time to visit Castiglione della Pescaia?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$231 NZD$255 NZD$260 NZD$236 NZD$231 NZD$272 NZD$341 NZD$383 NZD$253 NZD$208 NZD$234 NZD$236 NZD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°C

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

  • Total holiday rentals

    Explore 250 holiday rentals in Castiglione della Pescaia

  • Nightly prices starting at

    Castiglione della Pescaia holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,310 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Castiglione della Pescaia holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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

Destinations to explore