Vacation rentals with outdoor seating in Castiglione della Pescaia

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!

How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

Very peaceful and beautiful views from the rooms. Raffaella’s breakfast was very good and much appreciated! She gave amazing local food recommendations that are walkable from her house. She also helped us find parking in the city of Florence!

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 :)

The house is located on Chianti which views to vineyard and olive yard, the most beautiful view for an airbnb. Everything is fully furnished, a lot of welcome foods and drinks. The hosts give clearly instruction and very responsive. It was a wonderful time spending our holiday there.

Great location only 2 minutes walk from the Cathedral. Accommodation is airy and well equipped with its own lovely garden giving you a great place to relax so close to the centre. Francesca was always available and made us feel very welcome. Have already recommended this property to our friends.

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!

The stay in Letizia's apartment was just perfect! The apartment is very well equipped, nice and large and really offers everything you need. The balcony is a highlight – ideal for relaxing. The air conditioning also works perfectly, which made the stay particularly pleasant. The beach is only a 3-minute walk away, and the old town is easily reached in about 10 minutes on foot. Everything was great – thank you so much for the great place! I'd love to come back.

5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!

We stayed at Aleksandra's in Montalcino in the heart of Brunello, a breathtakingly beautiful area, for a week. The large property is fantastic and with the tranquility and the view just the right thing to relax and unwind. An unforgettable experience for the whole family. This is how you imagine a Tuscan holiday. We highly recommend the place.

Charming living room, bedroom and patio with a view that is unparalleled in beauty and tranquility. Beautiful room, well-stocked, everything extremely well cared for in detail by a person - Elena, although we did not have the opportunity to meet - who puts love into providing an experience that is absolutely worth repeating. The common areas are also extremely well-kept and comfortable.

This is Tuscany at its finest! Our stay at Casa Bonari was perfect. The villa inside was spacious, beautiful, comfortable, and wonderfully Italian. It was equipped with everything we needed. The exterior grounds were gorgeous and the views from the property in every direction were breathtaking. We made dinner and ate on the patio - it looked like a picture from a magazine. The villa is within easy walking distance of the charming Monticchiello which has a few excellent restaurants. We enjoyed strolling the picturesque streets and the incredible views of the countryside from the village. Our hostess, Valentina, was very gracious and helpful. We enjoyed meeting some of the friendly family members. They were so kind and left us with happy memories. We highly recommend Casa Bonari and hope to visit again.

A lovely apartment within walking distance of the beach and village. The outdoor space is not that large but large enough to sit comfortably. Inside it is much more spacious and very cozy and tastefully decorated by Angelo. Of all the comforts including a beautiful bathroom. Would go there again in a heartbeat and really recommended! André and Brigitte

We felt so comfortable between the fields in absolute peace. We were able to relax very well in the idyll. Everything is very well maintained and tastefully decorated inside and out. By car, you can also reach the pretty harbor town very quickly and can eat well and shop. David was always available for questions. We would definitely come back.

We had a fantastic stay at Keith’s beautiful apartment. We were four adults and a baby and had plenty of room. The views are outstanding - even better than the pictures - and the street is quiet and within walking distance to everything you could want to see in Porto Santo Stefano. Keith was responsive, friendly, and flexible with check-in when we ended up arriving quite late. We couldn’t have asked for a better stay!

What can I say except that Beatrice and her husband deserve a 10 with honors. Fantastic location, they are very kind. Everything was perfect. Try their aperitif, which is not just an aperitif but much more

Marco’s place is away from the hustle and bustle of Siena very quietly comfortable and super clean. The view from the balcony alone is worth the night rate. Close to all the lovely sights in Val D’Orcia. In a very quaint town with locals who actually live here. Marco is very responsive and clearly explained everything to us. Must try the pizza at Pizza I’ll Vecchio…a hidden gem in Tuscany

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!

It is a great place to stay and feel the quiet and peace of Tuscany! My family and I really enjoyed it. The apartment is really nice, with a unique style inside an ancient house. And without a doubt, it has one of the best views from the kitchen and terrace that I have ever seen!

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.

Very comfortable accommodations and gorgeous property and views

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

Matteo’s place has a really breathtaking view ! It’s also very quiet and peaceful. Also close to PSS via the shortcut. We had a wonderful time. Don’t miss a trip to Giglio !