
Holiday rentals with a pool in Poggibonsi
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Top-rated rentals with a pool in Poggibonsi
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Popular amenities for Poggibonsi rentals with a pool
House rentals with a pool

Infinity pool in Chianti area
"Perfect" is the only word that comes to mind for Anna's place. Such a serene location and perfect for a family. The view is just spectacular. We felt so at home and loved sitting out in the yard and by the pool. Anna provided us with a list of so many amazing things to do/see near and far. A must do is the pasta making with Vilma at the house-the most memorable and delicious meal from our trip! Can't wait to go back there to live more of the Tuscan life and enjoy the most beautiful view. Thank you, Anna, for hosting such a gem!

Cercis - La Palmierina
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!

Casa Bada - Barn
Great place and location. everything about the place and our stay was excellent.

Antico Borgo Ripostena – n. 9 Oil Mill
Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.

Private villa/swimming pool in Tuscany
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!

The Owl: view, pool and garden
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.

Casa di Lyndall - Entire house with exclusive pool
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 :)

Gaiole in Chianti Poggio Casabianca
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always received good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he could move freely. We would come back. It was an incredibly beautiful time!
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.
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.

Casa Rebecca with a small private pool
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

VILLA LE PERGOLE - Florence
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.

House between Firenze, Arezzo, chianti e Siena
We were immediately enchanted by this property. Everything here makes up the image that one can have of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good right away, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb pool, the shaded terrace, the hearty homemade breakfasts! It's more than a crush, this place is a gem! We'll be back!

Agriturismo Casavecchia, l'Olivo
We absolutely loved our stay and it exceeded our expectations. The staff were friendly and very helpful, the food was delicious and the apartment was a great size with all the amenities we needed. It was family friendly and our children loved the pool. It’s a beautiful location and very relaxing. We would love to come again. Thank you for making our holiday so lovely.

Ginestra: Private Pool Overlooking Florence
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.

Apartment with terrace and stunning view
The stay at Raisa's was incredibly beautiful. The accommodation and especially the view is much nicer than in the pictures. Raisa has gone to great lengths to make everything as pleasant as possible for us. The dogs (Saila and Yango) are mega cuddly, the pool is great and the entire property is really picturesque. Beautiful city trips etc. are easily doable by car and we would be happy to come back again sometime.

La Casetta
We can absolutely recommend it! Everything is as described in the text and can be seen 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 due to traffic to around 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 is the best place to park in Siena, how do you get to Florence, ...)
Home rentals with a private pool

Sole by Interhome
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.

Stone House with Exclusive Pool Codilungo in Chianti
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!

Explore nature in the center of Vigneti Chianti
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

Aurora by Interhome
We had a lovely week at this place. The outdoor area in particular was fantastic! Thank you and happy to come back!

Private Tuscan Villa, pool,Hot Tub, near Siena
Fabio’s house was absolutely wonderful! Janine was super helpful, and the place was so clean and comfortable. It fit our 2 large families easily! Thank you for letting us stay and relax and take in the gorgeous countryside!

Charming villa in the Chianti hills
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.

Villa il Palagio in the Tuscan countryside
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!!

Casa Luigi Suite with exclusive pool
We had an amazing stay here! The property is beautiful: great views, flowers and lemon/orange trees were blooming, and the pool was great plus super clean! The bnb was cozy with traditional Tuscany vibes. Giovanna and Luigi were amazing! Super friendly, loving, helpful, and funny 😁 highly recommended if you're looking for a peaceful country setting!
Quick stats about holiday rentals with a pool in Poggibonsi
Total rentals
20 properties
Nightly prices starting at
$124 AUD before taxes and fees
Total number of reviews
480 reviews
Family-friendly rentals
10 properties are a good fit for families
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Spiaggia Libera
- Cavallino Matto
- Teatro Verdi
- Palazzo Vecchio