Family-friendly holiday rentals in Guardistallo

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.

Incredible home, with stunning views! I hosted a group of friends here before my wedding, and we all agreed it was the most beautiful Airbnb we have ever stayed in. The hosts (Francesco and his wife Illaria) were extremely responsive and kind. They recommended a local chef to us, which turned into one of the best nights of our trip. 100% recommend and will be re-booking next time I travel to Tuscany.

We had a wonderful week in Gloria's house. Our four-legged friend also felt totally comfortable in nature. The house is small but nice and has everything you need. The property is a nice size and is perfect for eating outside, relaxing in the hot tub or just lying in the sun. The way to the house is a little challenging, but with a normal car and a little driving experience it can be mastered. Gloria was always available to us and gave us good excursion tips for the area in advance. Even with any inquiries, she always reacted very quickly and helped us. It is perfect for simply getting out and enjoying the nature and tranquility of Tuscany. We will be happy to come back!

We had a really good time at this place. It was spacious, clean, and worked perfectly for our group. There were plenty of bathrooms, and the house had all the amenities you might need for a comfortable stay. The outdoor space was a big plus—especially the terrace and patio area with the big table, which was great for hanging out and having meals together. The location is honestly perfect—super peaceful, but just a short drive to Florence, great local restaurants, and vineyards. Also, there was tons of parking space, which made things super easy for us. Check-in was smooth and the host was really helpful. Would definitely stay here again.

Top notch. Giacomo recommended some great activities to do nearby (after Lucca and Pisa). Very friendly family. Thank you!

The accommodation is in a large family building perched on a hill and offers a splendid view of the Tuscan landscape. The interior matches the photos perfectly. We find many trinkets, paintings, souvenirs of all kinds that evoke the generations that have succeeded each other in this beautiful house. The pool is exceptionally large and perfect after a day of discovery. Too bad there's no air conditioning, but Antiionetta provided 2 welcome fans. The car can be parked in the courtyard.

Amazing place and the place offered by Francesca is totally great. She was so kind and helpful. Totally recommended!

We can absolutely recommend it! Everything is as described in the text and as shown in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information for the journey and many great tips on site, always with the corresponding links. For example, our arrival was delayed to about 10:15 pm due to traffic. Was no problem, we were in contact and when we arrived, Andrea personally received us. And if we had a question during our stay, an answer always came very quickly. (Where is the best place to park in Siena, how do you best get to Florence, ...)

The pictures don’t do the beauty of the space justice. Maria, the housekeeper who lives in the basement unit was very discrete. Dawn was our host and set us up some incredible reservations, as well as helped us with a transportation issue. The view is otherworldly off the back porch, which overlooks olive trees. There are many adorable tortoises that live in the backyard and are very fun to watch. Close drive from the tram as well as many incredible restaurants. Take the cooking class with Maria!!! It was a trip highlight. If you stay here, you will definitely want a car.

Please do yourself the favor and book this space immediately. To call the home a palace would be an understatement. As a constant traveler, this is easily the most beautiful place I’ve ever stayed at. Perfect view of the Uffizi gallery and river Arno. A 2 minute walk to the Ponte Vecchio and many surrounding markets and Osteria’s. Frederico is an amazing host and now a good friend of ours. He accommodated us and was super patient when we were checking out. The home is extremely well curated with beautiful works of arts and sculptures. The living room area is a great big space with giant windows that can be opened and marble bath tub and shower. I will be dreaming of returning to see our friend Frederico in Florence very soon. He has a kind soul and was very warm with us. Side note: our favorite restaurant was the Osteria Toscanella. Only a 5 minute walk from the space. Please tell Tony from the Osteria that Richard and Geraldine from Texas say “Hola”!!! Everyone made us feel at home.

Wow-10 days spent at Alec's villa and could have stayed longer! The age and beauty of this place makes you feel transported back in time. From the stone walls, the detailed wall paintings, furniture and decor, to the solid doors easily hundreds of years old... We spent hours just speaking of it's history. The house is clean, spacious, and had plenty of room for our family of 8. It is situated on a small family vineyard at the top of an incredibly windey road. There outdoor space was safe/secluded for my kids. The hill made for wonderful beautiful views and sunrise. However, as with much of Tuscany, we were glad our rental cars weren't too big! The closest town is 5 minutes away and has a few restaurants... Though not somewhere you can have coffee or walk the streets. About 15 minutes away is San Casciano where you can find coffee shops, restaurants, stores etc. Alec is a perfect host... helpful, responsive, and answered dozens of questions weekly. Book dinner at A Casa Mia for sure!

Hands down our favorite part of our two weeks in Italy! Casa Al Poggio was our Tuscan home away from home. We went and did all the things… Florence, Cinque Terre, San Gimignano, Montepulciano, etc. But coming “home” to this place was the best. So peaceful and picturesque looking across the valley at the Badia Di Passignano. We cooked many meals in the well stocked kitchen and my husband loved the rustic BBQ. Fresh herbs in the garden and the smell of jasmine blooming on the patio. Book yourself extra time here…you won’t want to leave! Emanuele & Tamara are the kindest people. Take them up on all of their restaurant recommendations. Everyone one was a hit! We can’t wait to go back.

Christine and John were the best hosts, making this incredible location even more enjoyable. They went above and beyond, recommending restaurants, wineries and experiences that made our trip unforgettable. Christine also helped us get our lost luggage back, ringing the airport for us and liaising with a driver in Florence to pick it up and drop it off to us. Incredible service. Absolutely recommend!

Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.

Beautiful and rustic farmhouse placed in ancient olive grove. We had six adults and were extremely comfortable for our two week stay. Some days we never got out of the clean and refreshing pool. Family dinners were prepared in the perfectly functional kitchen served in the courtyard dining table Nicola was always availableto answer whatever ever came up. Loved the house and our Tuscan vacation

This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)

We thoroughly enjoyed our stay. It is a private, enclosed complex in beautiful surroundings. We had a wonderful view of the Tuscan countryside from the terrace. The apartment was very nicely and functionally furnished, very clean and very well equipped with everything one might need for a stay. The accommodation has access to a large swimming pool. There are many interesting places for short trips in the surrounding area. We had a very relaxing stay and will definitely want to return soon.

A very nicely located house, we were there with the children - a clear recommendation! In-house playground, play kitchen, pool, that's all a child needs for a week. Particularly noteworthy is the town of Montescudiao, not far from the property. Italy at its best! A small Italian idyll with a butcher, baker, coffee house, tobacconist and trattoria AND a very good upscale restaurant - Il Frantoio! The only thing was that there was no contact with the homeowner, as everything was handled professionally by a home care company. But it wasn't too bad, we bought wine and olive oil from the surrounding farmers and enjoyed a nice time in Tuscany...

What a magical stay! Christine is a true host and not only has curated a beautiful space but she also was perfectly attentive to us during our stay. The apartment was as comfortable as it is beautiful. We took advantage of the outdoor grill and swimming pool and although we explored the area we would have been just as happy to stay “home” all day. The recommendations for the area were true gems. We had breakfast our last morning and it was the perfect ending to our stay! I don’t think you can find a more perfect place.

We had a great stay! Simona welcomed us warmly and showed us everything in peace. The Airbnb is beautifully situated in the middle of nature – perfect for unwinding and unwinding. The place was very clean, lovingly and cozily. We felt completely comfortable and would come back anytime. Thank you for the wonderful time!

We had a truly wonderful stay at Villa Elena. The house and its grounds are beautiful and the location is excellent being close to some fantastic restaurants in the village and with the sea and Tuscan villages a short drive away. If you are looking for a quiet, serene and authentic environment to immerse yourself in the Tuscan Maremma and countryside, look no further. What stood out most of all was Serena's kindness and warm, friendly hospitality. From the moment we arrived we felt at home and whenever we needed advice or practical help Serena was so responsive and helpful. It felt like being in a home away from home, which we were truly grateful for. Thank you so much, we will be back! (Family with two small children)

My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.

Amazing location and beautiful location

We had a fabulous stay at the Villa. Laura was so responsive and handled all our needs. She pre booked all our events and was there to greet us when we arrived. We loved the views and kids enjoyed the pool. The wine tasting on property is a must and we thoroughly enjoyed the dinner they prepared for us at the villa. I highly recommend this beautiful spot. Sitting in the patio overlooking the Tuscan countryside was one of the highlights of our vacation. Thanks to Alessandro and his team. We hope to visit again someday!