
Family-friendly vacation rentals in Castiglione della Pescaia
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Top-rated family-friendly rentals in Castiglione della Pescaia
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Popular amenities for Castiglione della Pescaia family-friendly rentals
Family-friendly home rentals with a hot tub

Deal 2019 Tuscany Villa le Capanne with pool
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.

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

Apartment with garden in the heart of Tuscany
Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!

Relax in the countryside near the sea( Lavanda )
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!

Beautiful renovated barn in Tuscany
Beautiful spot in a peaceful setting. Gloria was a fantastic host. We had a wonderful stay.

Charming estate with views
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!

Country house La Meria
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.

Villa di Geggiano – Guesthouse
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

La Maison di Monica & Simona
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!

Back Home - Apartment in Pienza
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!

Emma's Home Apt "Earth"
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.

Small house
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!

Holiday in the Chianti Senese
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.

Sunny Seaside Cottage
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!

Romantic and cozy two-room apartment
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.

loft in the heart of Tuscan Chianti
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

Villa Castiglioncello - access to the private sea
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!

Exclusive Villa with Private Pool and Air Cond.
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.

Tuscan farmhouse near Siena + Cortona, heated pool
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!

Casa di Lyndall - Entire house with exclusive pool
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!

Apartment for 2 with super views+pool near Siena
Mario was very warm and a very very great host. We would always come back!

Splendid house with garden, pool, 5km from Siena
Ideal for a family vacation in Tuscany. Idyllic setting surrounded by hills and vineyards. The house was spotless and Lavinia's service was excellent!

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

Apartment 2doublerooms private fenced garden, pool
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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