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Family-friendly vacation rentals in Castiglione della Pescaia

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Castiglione della Pescaia family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A round jacuzzi filled with water is shown, surrounded by lush greenery and hills in the background. The scene captures a serene atmosphere, with part of the jacuzzi featuring a built-in space for drinks.
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars6 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Guest favorite
The image showcases a charming villa set amidst lush greenery, featuring a stone pathway leading to the entrance. A private swimming pool reflects the sunshine, while colorful flowers add vibrancy to the surrounding landscape. The rustic building displays traditional Tuscan architectural elements.
Farm stay in Sovicille
5 out of 5 average rating, 23 reviews

Tuscan Villa:Pool,Hot Tub,A/C,wi-fi,7bd near Siena

TimRating, 5 stars9 months ago
Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place
Guest favorite
A sunlit outdoor area features comfortable lounge chairs in vibrant colors beside a hot tub. Olive trees and shrubs surround the space, providing a serene backdrop. A gentle slope of green grass continues toward distant hills, enhancing the tranquil atmosphere.
Apartment in Montevarchi
4.91 out of 5 average rating, 104 reviews

Apartment with garden in the heart of Tuscany

Mary BethRating, 5 stars5 months ago
Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!
Superhost
A serene pool area features a curved, salt-water pool framed by a white railing. Light drapes billow gently in the breeze, enhancing the tranquil setting. The surrounding landscape includes rolling hills under a clear blue sky.
Home in Campo nell'Elba
4.9 out of 5 average rating, 147 reviews

Relax in the countryside near the sea( Lavanda )

AntonelloRating, 5 stars2 weeks ago
Isabella is a nice and helpful person, she welcomed us to her beautiful villa and immediately put us at ease. Great tips on places to visit and where to eat. The accommodation has all the comforts, beautiful salt pool, unfortunately not available since the season has not yet started. I'll definitely be back, thanks for everything Isabella!
Guest favorite
The exterior of the property features a rustic stone façade complemented by wrought iron details. A spacious terrace is equipped with a large umbrella and an outdoor dining area, surrounded by lush greenery, enhancing the natural setting.
Cottage in Radicondoli
4.92 out of 5 average rating, 131 reviews

Beautiful renovated barn in Tuscany

RachelRating, 5 stars2 months ago
Beautiful spot in a peaceful setting. Gloria was a fantastic host. We had a wonderful stay.
Superhost
A sunlit sunroom features large windows adorned with sheer curtains, allowing natural light to fill the space. A cozy white sofa is positioned next to a small wooden table with chairs, while indoor plants add a touch of greenery to the inviting atmosphere.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 255 reviews

Charming estate with views

BriRating, 5 stars2 weeks ago
We had such a lovely stay at Bernardino’s villa! He greeted us when we arrived and made sure we had everything we needed. The home is very charming and peaceful, and centrally located to explore Tuscany. Would definitely recommend!
Guest favorite
A ground-level countryside dwelling is presented with natural stone pathways and wooden shutters. Potted plants are positioned near the entrance. The exterior is complemented by expansive windows, providing views of the surrounding landscape under a clear blue sky.
Home in Catabbio
4.89 out of 5 average rating, 158 reviews

Country house La Meria

DamonRating, 5 stars6 months ago
We are an American and Italian family traveling through Italy and we highy recommend this special spot in the mountains. The landscape was beautiful and the breakfast was wonderful. We ended up arriving very late in the evening as their was a crash on the autostrada and Luca was very accommodating and communicative. We would stay here again.
Top guest favorite
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, 129 reviews

Villa di Geggiano – Guesthouse

LauraRating, 5 stars3 weeks ago
The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!

Family- and pet-friendly home rentals

Superhost
A panoramic view of Sasso Pisano is captured, featuring historic stone buildings nestled among lush green hills. The clock tower stands prominently, while tree-covered slopes provide a natural backdrop, highlighting the town's rustic charm and tranquil setting.
Apartment in Sasso Pisano
4.78 out of 5 average rating, 189 reviews

La Maison di Monica & Simona

JurgitaRating, 5 stars1 week ago
Really enjoyed the stay: the place is spacious and cozy (even more beautiful than in the pictures :)), there was everything you need: bed linen, towels, everything equipped with kitchen. The hosts are friendly and although they don't speak much English, but they explain everything:)... The town is charming too - full of historical buzz. There is a small thermal spring quite close (from the property maybe 5 min walk) - quite hot so only one of us bathed, but our feet were all soaked;)... We had a wine at the townhome's bar - it was very nice to interact with the locals. Literally, the warmest feedback - thank you for everything!
Top guest favorite
An open living space features a colorful polka-dotted sofa and a small dining table surrounded by vibrant chairs. The kitchen area is organized with shelves displaying kitchenware and appliances, with a warm wooden ceiling enhancing the cozy atmosphere.
Apartment in Pienza
4.9 out of 5 average rating, 163 reviews

Back Home - Apartment in Pienza

MorganRating, 5 stars1 month ago
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!
Top guest favorite
A shaded outdoor seating area is surrounded by lush greenery and flowers, featuring two woven chairs and a hammock hanging from a tree. The background offers a view of the coastline and distant hills, creating a peaceful retreat.
Vacation home in Porto Azzurro
4.89 out of 5 average rating, 35 reviews

Emma's Home Apt "Earth"

JoachimRating, 5 stars9 months ago
Staying with Elena was something special. The location offered a lot of peace with a great view of the sea. The style and coolness of the house in the summer, the shady and lounge-like places outside offered almost a kind of club atmosphere. The "price" for this is about 20 minutes' walk to the harbor of Porto Azurs.
Guest favorite
The exterior of the property showcases a covered terrace bordered by lush greenery. A stone barbecue is positioned beside the terrace, with a paved pathway leading to the entrance. Wooden seating is visible, providing an inviting outdoor space.
Apartment in Marciana
4.79 out of 5 average rating, 100 reviews

Small house

KarinRating, 5 stars8 months ago
We found the apartment very clean and as described, and the hosts were very friendly. They gave us tips for excursions upon arrival. Anna Maria and her husband have created a little paradise here. If you are looking for peace, you will find it in this beautiful environment. The terrace is not only perfect for sunsets, but also for the view of the starry sky! The space was sufficient for us with two children, as we were mostly outside anyway. We can recommend the small shop in neighboring Colle d'Orano. We enjoyed the week in Patresi very much!
Superhost
A serene pool reflects the vibrant colors of the sunset, with gentle waves suggesting a peaceful ambiance. Lush greenery surrounds the area, creating a natural setting. The silhouette of a building and a lone tree can be seen in the background against the colorful sky.
Home in Staggia
4.87 out of 5 average rating, 39 reviews

Holiday in the Chianti Senese

JosefinRating, 5 stars9 months ago
We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.
Superhost
Vacation home in Porto Santo Stefano
4.83 out of 5 average rating, 35 reviews

Sunny Seaside Cottage

BrigitteRating, 5 stars9 months ago
We had a wonderful week at Ale's cottage, with direct sea views and 2 islands. Ale sent a very accurate description of how to find her, incl. Photos of the main branches. It was easy for us to find. We were there with an SUV and 2 e-bikes, so we could easily reach the parking lot to our chalet, also down the slightly steeper road to the chalet. For all vehicles that do not have a higher wheelbase, there is a parking space above Ales house, you are downstairs in 3 -4 minutes walk. Ale gave us a warm welcome, and provided us with tips for restaurants and beaches in the vicinity. Our chalet had everything, there were two of us. 2 terraces, one with outdoor kitchen, in the bedroom there is air conditioning, which we used to fall asleep. We enjoyed the view over the sea to the islands from morning to evening, there was always something to see. We had a great time, thanks Ale!
Superhost
The image captures a serene landscape featuring a lush green lawn bordered by dark green trees. A small heated mini pool is positioned nearby, providing a relaxing view of rolling hills under a partly cloudy sky. The peaceful atmosphere is enhanced by the natural surroundings.
Condo in Ponteginori
4.87 out of 5 average rating, 15 reviews

Romantic and cozy two-room apartment

GabriellaRating, 5 stars8 months ago
Beautiful place between Cecina and Volterra to stay in complete tranquility and relaxation in the Tuscan hills, panora and fantastic sunset. Convenient to visit medieval villages and not far from the famous Etruscan coast and for those who love cities you can reach Pisa and Siena. Fausto is a fantastic host, accurate and very helpful, but not intrusive, he gave us directions to places to visit, typical beaches and also very nice restaurants nearby. Our stay was pleasant and relaxing what we wanted was to stay away from the confusion and daily stress, if this is what you are looking for here you can find it... you will only hear the "noise" of cicadas.
Guest favorite
A spacious living area features a wooden-beamed ceiling and large windows allowing for natural light. A red sofa and rustic wooden table create a comfortable setting. A stone fireplace is positioned in the corner, adding a warm element to the welcoming environment.
Home in Gaiole in Chianti
4.8 out of 5 average rating, 100 reviews

loft in the heart of Tuscan Chianti

CharlotteRating, 5 stars6 months ago
We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.

Family-friendly home rentals with a pool

Guest favorite
A modern villa with a unique architectural design features large glass windows reflecting the pool's surface. The turquoise infinity pool is surrounded by lounge chairs and an umbrella, offering an inviting outdoor space with lush greenery in the background.
Villa in Rosignano Marittimo
4.92 out of 5 average rating, 25 reviews

Villa Castiglioncello - access to the private sea

JürgRating, 5 stars7 months ago
House, location: right by the sea, fantastic views, spectacular sunsets, large house with special architecture offers plenty of space and privacy, ideal for a large family. Various garden terrace areas. Everything very well maintained and well equipped. Camilla is a very warm and competent host. We will be happy to come back!
Guest favorite
Villa in Pergine Valdarno
4.82 out of 5 average rating, 17 reviews

Exclusive Villa with Private Pool and Air Cond.

KaraRating, 5 stars10 months ago
Our stay at Villa Chiara was nothing short of delightful. Nestled in the hills it offered a picturesque view of the Tuscan countryside. The villa itself was spacious and well maintained. It felt like home away from home. The pool and back patio are surrounded by lovely flowers, herbs and olive trees. Offering a spectacular view of the evening sunsets. The location was perfect to take short day trips to Siena, Florence and Montepulciano. Highly recommend for a serene, peaceful and relaxing getaway.
Guest favorite
A well-maintained pool area features a clear swimming pool in the foreground. Sun loungers are positioned beside the pool, shaded by umbrellas. In the background, the farmhouse with blue shutters is surrounded by lush gardens and trees, offering a serene outdoor space.
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars6 months ago
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 135 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars6 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Guest favorite
A tranquil pool with clear blue water reflects the sky, surrounded by lush greenery and colorful flowers. Rolling hills and a scenic landscape are visible in the background, enhancing the serene environment of the property.
Apartment in Sovicille
4.9 out of 5 average rating, 131 reviews

Apartment for 2 with super views+pool near Siena

JanRating, 5 stars7 months ago
Mario was very warm and a very very great host. We would always come back!
Superhost
Apartment in Siena
4.71 out of 5 average rating, 7 reviews

Splendid house with garden, pool, 5km from Siena

AlbertoRating, 5 stars3 weeks ago
Ideal for a family vacation in Tuscany. Idyllic setting surrounded by hills and vineyards. The house was spotless and Lavinia's service was excellent!
Superhost
Home in Piombino
5 out of 5 average rating, 13 reviews

Between the sea and tradition, an anti-stress vacation!!!

AlbertoRating, 5 stars8 months ago
I've spent 10 days of relax with my family, we had great time, the place is very quiet and relaxing. Very clean and tidy. Air conditioned helped us in the hottest days. It's very convenient to the sea, although we spent our days of holiday by the pool. Highly recommended!!!
Superhost
Apartment in Prato d'Era
4.9 out of 5 average rating, 20 reviews

Apartment 2doublerooms private fenced garden, pool

LucileRating, 5 stars8 months ago
We had a pleasant stay at Silvia's place. We stayed for 2 weeks which allowed us to discover Tuscany. We had an issue with the fridge. Silvia and her husband were very responsive. We were lucky enough to discover Silvia's family via a cooking class in her parents' agroturismo. We loved it! The space was very clean and spacious. We enjoyed the pool with the heat. Volterra is 10 minutes away by car. And the landscapes are beautiful.

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

  • Total rentals

    230 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    140 properties include access to wifi

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