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Family-friendly vacation 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.

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Top guest favorite
Aerial view of the agriturismo surrounded by lush green hills and fields. The property includes a swimming pool, framed by rows of tall cypress trees that create a natural boundary. The rural landscape extends into the distance, illustrating the serene environment.
Condo in Asciano
4.92 out of 5 average rating, 177 reviews

Loggiato 3 apartment in Tuscany near Siena

The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.

Guest favorite
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
4.95 out of 5 average rating, 111 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 favorite
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 favorite
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 favorite
The exterior of a renovated stone house is framed by greenery, featuring large wooden doors that provide a welcoming entrance. An outdoor dining set is visible on the patio, surrounded by carefully maintained gardens and trees, evoking a serene countryside atmosphere.
Condo in Cinigiano
5 out of 5 average rating, 105 reviews

Spinosa Apartment in Podere Capraia

Two-room apartment on two floors, recently renovated with good taste furnishings: living room with sofa bed (1 and a half places), dining table, TV, WiFi. Kitchenette with oven, fridge and dishwasher. Bathroom with shower, toilet, and bidet. Upper floor, open attic double bedroom. Exit to equipped front patio. Heating (from 10/15 to 04/15), mosquito nets. Small and medium-sized pets allowed. Swimming pool (open from Jun. 1 to Sept. 30) shared with Solengo apartment

Top guest favorite
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.

Top guest favorite
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. in our laundry room to those who request it). We recommend a 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 Convenient location to visit Tuscany and Umbria.

Guest favorite
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 favorite
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 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 surrounded by nature.

Top guest favorite
A charming stone house is surrounded by lush greenery and colorful flowers. The exterior features a thatched roof and several wooden windows, with a seating area adorned with potted plants. Mature trees provide shade, creating a peaceful outdoor atmosphere.
Home in Pancole
4.99 out of 5 average rating, 143 reviews

Casa Pancole

Beautiful stone house completely and tastefully renovated, surrounded by nature, ideal for privacy, close to places of interest such as Grosseto, Terme di Saturnia, Alberese, Parco dell'Uccellina, Marina di Grosseto (in the cold periods there is a pellet stove that heats the rooms, the pellet is an additional cost to be requested, thank you) tourist tax to be paid directly on site

Top guest favorite
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, 241 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 favorite
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. priceG$27,846 GYDG$30,777 GYDG$31,406 GYDG$28,474 GYDG$27,846 GYDG$32,871 GYDG$41,246 GYDG$46,271 GYDG$30,568 GYDG$25,124 GYDG$28,265 GYDG$28,474 GYD
Avg. temp8°C8°C11°C13°C18°C22°C25°C25°C21°C17°C12°C9°C

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

  • Total vacation rentals

    Explore 250 vacation rentals in Castiglione della Pescaia

  • Nightly prices starting at

    Castiglione della Pescaia vacation rentals start at G$6,281 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,310 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Castiglione della Pescaia vacation rentals include wi-fi 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

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