Kid-friendly vacation rentals in Castiglione della Pescaia

Home away from Home ❤️ loved the town that was walkable to everything. After two busy days in Rome, my husband and I enjoy walking to wineries, finding hidden churches and eating at the wonderful local restaurants. This Airbnb is a true gem ! Grazie- The Mixon Family

We loved the villa. It was private and had an incredible setting. Ivan was very responsive and incredibly helpful in suggesting restaurants and other activities. The only issue we had was finding the unit when we arrived. It was a little confusing at first to find our way to the villa.

We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!

We felt like kings of the castle in Stefano and Sylvias’s place. Top of a hill with expansive views and always such a beautiful breeze. San Quirico was lovely as was Bagno Vignoni at the bottom of our hill. We could see the twinkling lights of Pienza and Montepulciano both of which were an easy drive away. Generosity in the way the villa was presented and our hosts’ welcome, with many wonderful local suggestions. Would highly recommend.

Giovanna was a great host. Great place!

The Siena Secret Garden apartment was amazing. We loved the location, and it was quiet and comfortable and stocked with a lot of beautiful art, books, and movies. Would definitely stay here again!

We had an amazing time at Mario & Cristina’s place. The house was absolutely beautiful, (and has a really cool history; it was fun to stay in such a historic building) and the garden was so so lovely! (We loved hanging out with Signore Tartaruga! 🐢) Located right in beautiful medieval San Gimignano, close to everything you need (especially the world’s best gelato at Dondoli’s!) It was a wonderful stop on our honeymoon and San Gimignano will have a special place in our hearts forever! Grazie mille Mario e Cristina! We hope we can return one day!

We are delighted with this vacation at Vanda's, where the location of the accommodation allows easy access to many sites to visit in the area. The house is quiet and well equipped. The garden offers a green and shaded relaxation area. Vanda is an extremely friendly and discreet host who takes care of her visitors and who succeeds, despite language difficulties, in establishing a caring atmosphere. We were privileged to have met him and we will treasure our time.

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.

A peaceful place, quiet, clean in nature, everything is in the room, we didn't need anything extra

The perfect place to explore Chianti each day. We stayed 5 nights and it was just perfect. Great amenities, beautiful pool, bbqs and lovely areas to sit and enjoy the views and the sunset. Always fabulous to come home to. Our upstairs apartment was spacious, comfortable and all we required with a lovely view. We had great recommendations from Silvia which we followed up on. Great to have restaurants nearby. Reasonable- highly recommend.

The accommodation is virtually right on the water and surrounded by bars and restaurants. It's just a few meters to the old town. We felt very comfortable and highly recommend this place.

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

My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!

Spectacular view as pictured. Since the apartment is located in the historic center, you need to park at a parking lot a little outside the center (which is the case for all the apartments in the area). Apartment was overall more spacious than expected. Although the balcony was quite narrow, the beautiful view made up for it. Location was convenient to walk to many shops and restaurants.

We have now stayed in Elisa and Alessandro's accommodation for the second time – and it was simply beautiful and absolutely relaxing again! The place is a real oasis where you can unwind perfectly. Elisa and Alessandro are extremely helpful and warm. They provided us with great tips for activities and restaurants, so we could enjoy our stay all around. We'd love to come back and highly recommend this place!

Alessio and Beatrice were perfect hosts. The place couldn’t be in a better location, right on the north end of the Main road through San Gimignano. Having the top floor really made it peaceful despite the sometimes bustle of the town. The apartment was beautiful and comfortable; a great base for exploring San Gimignano and the surrounding Tuscan countryside!

Excellent accommodation, house as shown in the photos and description, located in a very nice little village. Clean and tidy property, Host always available for any information and kind.

A beautiful Agro tourismo right in the lap of nature…very close to the picturesque Pienza town and with gorgeous views of Tuscany rolling hills all around the house.. Bianca’s father met us upon arrival and explained us all the details about the house, his farm, olive oil making and the background of the place.. They stay on the first floor of the house and Airbnb is on ground floor… The house was built in 1576 and it was one of its kind of experience to be staying in it… The house is quite spacious and very well decorated. We stayed here for 3 nights and did 2 day trips - 1 to Florence and other to Siena ( a must visit place with marvellous cathedral and piazza del campo ) and picture perfect Chianti region.. Having a car is absolutely necessary as the place is 8-10 km from Pienza and public transport is minimal… Regards, Sachin

We had the most fantastic stay at Antonio’s as a couple with a young baby. Everything in the apartment is as it appears in pictures. If is so practical and perfect. Also, Antonio has really great furniture, no IKEA here. He set up a pack n play for the baby. The patio was the crown jewel and the view was stunning. In June the sun was high quickly and the patio received shade early on in the day. Bed was firm. kitchen small but efficient. Outdoor cooking was lovely. The apartment was stocked for cooking and even toiletries. AC in the bedroom but doors open provided plenty of fresh air to keep the apartment cool during the day. Walking into town with was easy, driving is too on weekdays. The apartment has an elevator to reach the top floor, but you do need to bring the bags up two flights outside from the street unless you have a small car that can reach the driveway. We would not hesitate to stay at Antonio’s again!

Maria’s place was beautiful and exactly as described! It was bigger than expected and had a cute balcony we really enjoyed spending late afternoons relaxing! We had a great time in Montepulciano, it was relaxing and slow paced after a busy few weeks before ☺️ Maria provided local recommendations and was always responsive. If you’re thinking of booking here I highly recommend!

Filippo was the best host to have. He and his family are the most kind people I interacted with throughout my entire trip to Italy. The space itself is just as it is listed, everything worked perfectly, and we enjoyed our stay. I would highly recommend staying here. Being on the top floor of the complex gives a great view of the surorunding area and it was cool and breezy with the windows open. I could not have asked for a better experience and homebase for my travels.

Francesco was the perfect host very communicative and responsive when needed - the unit was spotless and nice decor - loved being in the little town walking to the 3 lively restaurants, grocery and coffee shop not to mention the fabulous vineyards that surrounded the flat - we did some wonderful walks and did side trips to cute little towns - Would recommend highly

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.