Kid-friendly vacation rentals in Castiglione della Pescaia

Stepheno was very helpful and was flexible with our check in. He even helped us book a super nice local restaurant. The apartment was very well equipped and decorated, and had everything we needed. The view over the valley and vineyard was amazing. We wish we could stay longer.

The place is a good base to visit local hill top villages and to access the beach. The hosts were very responsive and we enjoyed our stay.

Breathtaking location with views that are exactly what you want in the Chianti region. It was a beautiful place and was very nicely setup. Extremely responsive and helpful host. He provided recommendations and was quick to respond to questions. The house is centered nicely within the region and allows access to many different villages, wineries, and restaurants. An amazing experience and I highly recommend!

We really enjoyed our stay. The location is stunning with a super nice view. The flat is super well equipped and Daniela was a great host

I was in Castiglione della Pescaia for a week with my family and dog. I had a really good time at Flavia's place, very clean, very nice location and well-kept garden. I have to say that it is the ideal place to relax and enjoy the tranquility of a vacation.

If you are looking for a little piece of heaven look no further. Vignoni Alto is peaceful and incredibly beautiful. Stefano met us and showed us everything about the apartment and the historic hamlet. His instructions and recommendations were very helpful. The apartment is not far from the restaurants in Bagno Vignoni. Stefano really is a perfect host—responsive, friendly and proactive. Our only regret was that after a week we had to leave.

Staying at Torre “La Lambarda” Suite was an absolute dream come true. Nestled atop the enchanting village of Monticchiello, this historic tower offers breathtaking panoramic views of the Val d'Orcia that are simply unforgettable. The suite itself is a perfect blend of medieval charm and modern comfort, with every detail thoughtfully curated to enhance the guest experience. Although I didn’t meet Deb personally, her team provided outstanding hospitality throughout our stay. Every member of the staff—both at the property and at the wonderful restaurant—was warm, attentive, and genuinely kind. Their care and professionalism made us feel incredibly welcome and well looked after. Dining at Deb's Lounge was a true highlight. The food was exceptional, the ambiance cozy and intimate, and the staff went above and beyond to make every meal special. This stay was more than just a vacation; it was a magical journey into the heart of Tuscany. I wholeheartedly recommend a stay in the Tower.

We thoroughly enjoyed the stay. Everything was very clean. Such a great environment. We traveled with a 1-year-old child and were very warmly received. For my daughter, there were many toys, a crawling blanket, baby bed and high chair. The small playground was also impressive. Our highlight was the great sunset and of course the most beautiful pool we have experienced so far. We can only recommend it!

Large, beautiful space. Very good location. With great restaurants around. Very good shower. Good beds. Well-equipped kitchen. The host always responded quickly and attentively. There is a little more noise in the bedroom with single beds, as there are some bars downstairs. But it has good windows that seal out the noise well. I hope I can come back. We really liked it!

This was such a dream. If you want a beautiful, private place to relax and play out your medieval Italian fantasies, this is the spot. Gorgeous, walkable (though a steep hill) to the main part of town and all the delicious restaurants. And simply unbeatable views. Not to mention Rosalia is such a gem. I wish I could have stayed forever.

Apartment 100% as described. We were pleasantly surprised: the apartment is definitely spacious, fresh and equipped with every comfort. The furniture is very modern. Impeccably clean. The location is strategic: in less than a minute on foot you can find yourself in the main street of the center of Castiglione with numerous shops and restaurants (a tip: always book for time because you risk staying without dinner! We were in Castiglione in the week of August and without booking it was difficult to find a place even late in the evening). In a few minutes by foot you can find yourself on the waterfront where there are many beach establishments but also numerous free beaches. Right outside the apartment, the supermarket is very comfortable! Niccolò and Daniela were always kind and super helpful: we especially thank Daniela for all the tips she gave us!!!! Not recommended!

Wow!!! What can I say about this most magical place that hasn’t already been said? 10/10 recommend Simone’s place. We will be talking about this stay for years to come. The property, the communication, the hotel amenities (restaurant Zita was wonderful but the spa massage experience was out of this world), the scenery. Just wow! Book this place while you can. We feel so lucky to have been able to stay here on our 2 week Tuscany adventure. Grazie!

I stayed there for 4 days with my family, a well-kept and clean house, very close to the sea and the center of the village. We had a great time, a wonderful place. The lady was precise in her directions and available to us when we needed her. We spent 4 fantastic and quiet days. i recommend it to everyone.

Great location and host was there to greet us and let us in. Town was wonderful.

This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.

Spectacular view. Relaxing after a long trip thru wineries. Town was very cute and comfortable

We stayed for 5 night and enjoyed this large, well appointed two story apartment. The place was warm and inviting and was an authentic home to be a unique setting. My family enjoyed the surroundings and there was plenty of restaurants to close from. Be prepared to tackle the 52 steps to the apartment door which my 90 year old mother managed twice a day. Keeps you healthy.

Very pleasant stay in the historic center of Chiusdino, a great place to visit the beautiful area. Apartment clean and equipped with everything you need. Franca is very helpful and proactive. Recommended.

This was by far the most beautiful view we have ever had at an Airbnb or hotel room. The house was beautiful, but the sunrise from the balcony is something I will remember forever. Vittorio also offered recommendations, and Fulvia was flexible with our check in. The apartment is in the perfect spot to become familiar with town. We want to come back to stay here again. Thank you!

We loved the place! Porto Santo Stefano is peaceful and charming. We took the ferry over to Giglio Island one day and rented a scooter. Really a wonderful little getaway. Thanks Antonio!

I had a very comfortable stay with Filippo and his family are very friendly. The flat is designed in a very tasteful way and despite not having a separate bedroom, the direct exposure to the flat entrance door was not a problem for me. I would happily book it again. Ciao!

The apartment is in Massa Maritima, a very picturesque village. The location is right in the heart of the village. There are very good restaurants nearby.

Beautiful location picturesque

I can’t say grazie enough to Gessica and Bernardino! Such nice people. The apartment is one of the best Airbnb’s I’ve stayed in. Pictures don’t do it justice. It has everything you could ever need. The view from the balcony made it hard to leave. Hopefully we will be back! Grazie Mille!!