Family-friendly vacation rentals in Pienza

If I could move in here permanently, I would. What a gorgeous stay with responsive and respectful hosts. Everything was as described, the hot tub was glorious, and we loved looking through the binder of photos of painstaking restoration over the years.

What a lovely spot to stay! The rental is quite large, with a spacious downstairs and a nice bedroom upstairs, and the views are amazing. It is located in a gorgeous part of Tuscany. Hosts were friendly. I especially appreciated the hot tub!

I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!

Alex was lovely and very responsive. The place is great, would be perfect for a family or a group travelling. Great spot to explore the surrounding area

If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!

We had such a great time at this AirBnB. It is a very peaceful and private place, perfectly to disconnect and relax. The hot tub and sauna are a great addition and invite to enjoy the surroundings. Location wise you need a car and prepare to drive a bit more in case you wanna explore Tuscan cities. I would still argue it is worth it as you get a great place to stay.

Our family loved staying in Fernanda’s apartment! My husband and I had visited Montepulciano two years ago, stayed at Fernanda’s place and loved it so much we came back with our three boys. Everything is so lovely and welcoming and Fernanda is the best hostess. She even made local dinner reservations for us. Thank you for everything, Fernanda!!

Chiusi may not be a major hilltop town but it is very special because it lacks the tourists. We had plenty of restaurants to visit in the week we stayed, and lots of historic sights to see. You do need a car to visit surrounding towns but the peacefulness of Chiusi makes it delightful. Rafaels place is perfect with the balcony and sublime views. He was an exceptional host who did not impose on our privacy but always friendly and helpful. I would highly recommend this place and town.

Great flat to explore Cortona! Excellent location and had everything you need

We had an amazing week long stay!! Sabrina is a fantastic host! The apartment was SO clean and comfortable and had everything we needed. Breakfast each morning was very yummy and fresh! We did the dinner one night and it was so amazing! Location is great too. Easy drive to many close by towns, grocery stores, and restaurants. The property is beautiful with lots of flowers. A little too cold for the pool during our stay but our kids loved the swing set and teeter totter. Absolutely recommend staying here!

We were welcomed by Sabrina's dad. He's a very nice man. He even shows us the way to the grocery store. The accommodation is very clean with lots of amenities. And what about the view is quite beautiful. This is a place to stay that I would recommend without hesitation. Thanks to Sabrina and her family.

My husband and I very much enjoyed our stay at Jenny’s Barn as part of our honeymoon! Jenny was so helpful, and had great recommendations. The place was so quiet, peaceful, and private. We enjoyed having dinner and breakfast every day on the patio. Everything was so well stocked and thoughtful! We definitely recommend!

We loved our stay. The host was amazing, and the house had everything we needed. The internet was very fast and supported my work requirements back in the USA. The views are spectacular, and the property is very private. Thank you, Irene, and family. I especially appreciated your help in getting me my new computer charger after mine broke. Have a great spring!

This accommodation has a really nice view. The bedding was clean and the bathroom was clean. There are two swings, a playground with a slide, a garden, and the kids were happy with animals such as mountain rabbits, cats, mountain birds, snails... etc. I was grateful that the hosts were so kind and sweet. I recommend this accommodation that I want to go to again.

Our stay at Paolo’s was incredible! The apartment was perfectly appointed, so comfortable and absolutely spotless. The amenities are well thought out and has everything you need for a short or longer stay. We greatly appreciated how kind, helpful and responsive Paulo was and the location is just so peaceful and breathtaking! Highly recommend!

Fabulous location with scenic views in a beautiful town. Everything you need to do full self-catering, nice bed, good shower. Antonio was great in all our interactions, very quick to respond and helped us out with the parking a few times (you typically have to park 500m away, but it’s a lovely 10 min walk). We definitely plan to return and stay here again, maybe even next year!

We both throughly enjoyed our stay and found it to be very peaceful home, whilst we explored the local region.

We had a great time at Clarissa and Antonio's cottage which is in a beautiful and quiet location but close to the center of the village of Radicofani. You can walk there and there are small shops and good restaurants. The cottage is well-equipped, clean and very nice. We were greeted by Sara and Marcello who are very friendly and very nice. We really enjoyed the small welcoming touches. The cottage is in a very good location geographically for visiting the main villages of Tuscany and enjoying beautiful landscapes. We were able to enjoy the pool at the end of the stay which was very nice. We would happily stay at Clarissa and Antonio's again.

Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!

My husband and I adored the tranquility of this stay. Our host Oscar was so proactive, responsive, and helpful. We are so grateful for the kind acts of service Oscar and his team extended towards us. I have Celiac and they took into serious consideration ways to prevent cross contamination and made sure that there were options available for me. Their restaurant was likely the best food that we’ve tasted throughout our stay in Italy! The lobby is filled with its aroma of fresh herbs being cooked. We also adored the little furry friends that would hand around our porch! He had a team of people who would take us to and from the nearest train station and were extremely flexible! The stay is up a mountain so we were so thankful there was someone skilled enough to drive us up and down! Oscar, thank you for everything! We definitely plan to visit again and strongly recommend that anyone stay at your accommodation for peace, tranquility, and amazing food!

Giulia and Elisa were super nice hosts - always reachable by cell phone or on site 😊 If you want to relax and enjoy the tranquility, it's just a great place, with a beautiful pool and fantastic views.

Words do not do Francesco and Cecilia’s villa justice. We have stayed at many places, but this one is tops! Beautiful villa and surroundings. Great breakfast supplies (which we did not expect). Tremendous space, privacy,and beautiful landscape! We slept late most days because the loudest sound was the bumblebees in the stunning jasmine outside and the birds. We like to cook and the kitchen was fantastic. Everything was fantastic, including our very wonderful hosts!!! We will go back!! Great experience!!

We had a lovely stay! Elisa and Alessandro are so kind and very helpful with anything we needed. They made a reservation at a restaurant for us when everything was fully booked. Thank you for your great hospitality!

Paula has not only created a beautiful sanctuary that perfectly reflects Tuscan culture, but offers wine tasting and a vineyard tour on her property. The location of this gem of a place is centrally located in the Chianti region , making it a perfect home base for day trips to Assisi, Firenze and nearby small villages that offer great restaurants and quaint shops. The region is cycling friendly, as well as offering places for day hikes. Staying here for five days was one of highlights of our Italian adventure.....and we highly recommend experiencing the perfect place to stay in Tuscany and the warmth and friendliness that Paula, Ferderico and her staff offer!!