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Holiday rentals with a pool in Poggibonsi

Find and book unique homes with a pool on Airbnb

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Popular amenities for Poggibonsi rentals with a pool

House rentals with a pool

Top Guest favourite
Home in Barberino Tavarnelle
5 out of 5 average rating, 108 reviews

Infinity pool in Chianti area

KrisRating, 5 stars2 weeks ago
"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!
Guest favourite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
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!
Guest favourite
Home in San Martino
4.94 out of 5 average rating, 212 reviews

Casa Bada - Barn

RaymondRating, 5 stars3 weeks ago
Great place and location. everything about the place and our stay was excellent.
Superhost
Home in Pievescola
4.93 out of 5 average rating, 106 reviews

Antico Borgo Ripostena – n. 9 Oil Mill

DanielRating, 5 stars2 weeks ago
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.
Guest favourite
Home in San Miniato
4.92 out of 5 average rating, 133 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars2 weeks ago
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!
Superhost
Home in Figline Valdarno
4.96 out of 5 average rating, 108 reviews

The Owl: view, pool and garden

JasonRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 137 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
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 :)
Superhost
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars4 weeks ago
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

Guest favourite
Condo in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment.

TomRating, 5 stars1 week ago
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.
Guest favourite
Condo in Figline e Incisa Valdarno
4.93 out of 5 average rating, 472 reviews

Casa Rebecca with a small private pool

MuskanRating, 5 stars2 weeks ago
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
Guest favourite
Condo in Rifredi
4.92 out of 5 average rating, 167 reviews

VILLA LE PERGOLE - Florence

JennaRating, 5 stars1 week ago
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.
Superhost
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars1 week ago
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 favorite, this place is a gem! We'll be back!
Guest favourite
Condo in Figline Valdarno
4.87 out of 5 average rating, 54 reviews

Agriturismo Casavecchia, l'Olivo

AnthonyRating, 5 stars3 weeks ago
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.
Top Guest favourite
Condo in Castellina in Chianti
4.92 out of 5 average rating, 60 reviews

Apartment with terrace and stunning view

LeonRating, 5 stars1 week ago
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.
Guest favourite
Condo in Casole d'Elsa
4.93 out of 5 average rating, 156 reviews

La Casetta

RamRating, 5 stars1 month ago
Both Barbara and Andrea were very welcoming and forthcoming when we encountered a hitch in our travel plans. They are unusually friendly, and accommodating hosts. The house is a great base for exploring the surrounding area and is tastefully decorated. Highly recommended!
Top Guest favourite
Condo in Barberino Tavarnelle
5 out of 5 average rating, 28 reviews

Entire house for couple with exclusive pool

BrandonRating, 5 stars8 months ago
Great stay! Beautiful views and great location only about five minutes from the main highway to go north to Florence or south to Siena.

Home rentals with a private pool

Guest favourite
Home in San Casciano Val di Pesa
5 out of 5 average rating, 5 reviews

Sole by Interhome

MarkRating, 5 stars2 weeks ago
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.
Guest favourite
Home in San Casciano In Val di Pesa
4.84 out of 5 average rating, 92 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

JanetRating, 5 stars1 month ago
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!
Top Guest favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Explore nature in the center of Vigneti Chianti

BaileyRating, 5 stars1 week ago
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.
Superhost
Home in Pescia
4.86 out of 5 average rating, 21 reviews

Aurora by Interhome

NatalieRating, 5 stars3 weeks ago
We had a lovely week at this place. The outdoor area in particular was fantastic! Thank you and happy to come back!
Top Guest favourite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 47 reviews

Charming villa in the Chianti hills

JessicaRating, 5 stars1 week ago
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.
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars9 months ago
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!!
Guest favourite
Home in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 96 reviews

Casa Luigi Suite with exclusive pool

KatieRating, 5 stars3 weeks ago
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!
Top Guest favourite
Villa in San Ginese di Compito
4.99 out of 5 average rating, 129 reviews

Farmhouse , pool, 13 px. Lucca 10km

EduardoRating, 5 stars3 months ago
We had an amazing stay at Juri's beautiful villa in Tuscany! The place is super spacious, easily accommodating our group of 11, and it was spotless and very well maintained. Juri and his mom were incredible hosts—always responsive and ready to help whenever we needed anything. The location is also perfect for day trips to Florence, Pisa, and Lucca. If you're looking for a charming, well-kept and very clean villa with top-notch hospitality, this is the place. Highly recommend! Let me know if you'd like any tweaks!

Quick stats about holiday rentals with a pool in Poggibonsi

  • Total rentals

    20 properties

  • Nightly prices starting at

    $134 NZD 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

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Poggibonsi
  6. Rentals with pools