Holiday rentals with a pool in Grassina

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!

Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!

Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.

What a great place to stay while visiting Tuscany. The home is a renovated medieval watchtower located up a dirt road, tucked on a hilltop overlooking the valley. Jacopo, the host, was so kind, hospitable and responsive during our 5-day visit. Would definitely recommend this place to explore Tuscana.

Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)

Licio has been one of the best hosts I've had on Airbnb. Everything was great. I also fell in love with his house, the passage and all of Chianti. I hope to return!

Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!

We enjoyed Maria's great house. We were kindly received by Maria and her family, where we were welcomed with a bottle of wine and delicious cake. We were with 6 adults. There's plenty of room. It's great that every bedroom has its own bathroom. It is a beautiful house in a beautiful setting with a lovely swimming pool among the olive trees and it is really equipped with all comforts. The charger for the electric car is also very nice. We picked up fresh bread every morning from the local baker in the village, 5 minutes away by car. Good base for the beautiful cities such as Lucca, Siena, Florence. The beach is also a great option. We felt very much at home. Maria and family, thank you for the wonderful time in your beautiful home.

Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.

A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.

I will express a few words because otherwise I would go on too long. Simply perfect. Beautiful and very large house, fantastic pool, impeccable cleanliness. Responsive host is always present. Highly recommended. I'll definitely be back.

Benedetta is an amazing and gracious host, the property was easy to locate and the room was beautiful, absolutely amazing Tuscan style with beautiful views and a private pool. She also recommended us a restaurant for dinner and that was one of the beat meals we had in Italy! 100% recommend

Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.

Marcello’s place felt serene and relaxing and our time here was just delightful. We absolutely loved the lemon garden we had all to ourselves, the grounds of the property are picturesque with a joyful companion of Tommy, Alina and Pistacchio. All is beautifully maintained and the apartment is elegant and cosy. We did appreciate proper mosquito nets, stable and fast internet for working, a proper dedicated workspace, sparkling clean apartment, great kitchen equipment, a garden table with a parasol offering plenty of shade, sun loungers by the swimming pool and a that the pool was kept very clean for us to be able to refresh in it during the hot days. Marcello is so friendly, warm and communicative. He spoilt us with his kind generosity and hospitality that you understand immediately why he is a super host, he really cares about his guests. Thank you so much dear Marcello for making our stay so enjoyable. We hope to be back one day.

Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!

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, ...)

Incredible host. Incredible house. You feel like you are inside a postcard. The most beautiful views are all around you. We did not want to leave. Just breathtaking.

Our stay unfortunately ends tomorrow and it was beyond our expectations🙏🏻 The Villa was exceptional, clean, cozy with spectacular views of the Chianti Plains❤️ The Villa, the pool, the flowers, the plants, the nature that surrounded us, allowed us to enjoy our vacation far beyond everything we could have imagined! Our host ,Signore Boncorso , made our stay unforgettable thanks to its exceptional hospitality and valuable advice! Grazie mille! A perfect rating! 5 stars xxxxx A 5 Stars ⭐️⭐️⭐️⭐️⭐️ and more!

We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!

Beautiful location in the country side. Perched on top of the hill with 360 degree views of surrounding vine fields. We even got to see them harvesting the grapes.

We stayed in the villa for 3 weeks with my family (2 young kids) and it was absolutely perfect!!! Francesca was an incredible host, fantastic communication. The house itself was beautiful, clean and the pool was just magic. Close to Florence and all the wonderful towns nearby, we can’t recommend this place enough. Would stay again without hesitation.

We spent the most wonderfull 2 weeks here in this beautifull location. Hosts were the most helpfull, warm and friendly. Any troubles or questions we had, they helped and answered quickly. Their olive oil is also tasty, we can recommend it. The home was as pictured, clean and even in hot days relatively cool. Very lovely accommodation and the views were spectacular. Pool was a great joy during hot days. Location is great. We did not have a car rented but managed still to get around nicely. There is a short, about 15 minute hike to the bus stop to go to Florence but it is managetable when you reserve enough time. There is also a supermarket on the bus route which was great. Taxi from Florenze was not a problem. Getting a taxi here to go to Florence is harder and we recommend calling the taxi service and avoiding the application. This is if you are planning not to have a car. A wonderfull stay all in all. Highly recommend!

Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!

I looked at dozens of other ABBs before choosing Giovanna's place and I know I made the best choice after staying. The setting is absolutely beautiful and peaceful. Lounging at the pool was so nice. We had the pool all to ourselves which is hard to find with other ABBs. The home is a nice large space and very clean. The views out the window are great. Giovanna was so nice and welcoming just a wonderful person. We enjoyed having a drink with her and Luigi. I highly recommend her place.