
Vacation rentals with a pool in San Gimignano
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Top-rated rentals with a pool in San Gimignano
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Popular amenities for San Gimignano 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!

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

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.

Countryhometuscany - House with Garden -
Beautiful property with warm, welcoming hosts. The bed was exceptionally comfortable, and everything is tastefully decorated The kitchen is fully equipped, perfect for cooking meals at home. The pool was a great temperature, immaculately clean, and came with stunning views of the surrounding countryside. The entire setting is peaceful and relaxing, yet only a 35-minute drive to Siena and 50 minutes to Florence. We especially loved watching the sunset at the nearby five-star Belmond hotel. We went for drinks at 7pm, enjoyed live music, and were surrounded by the heavenly scent of jasmine. There is no air conditioning but the fans were absolutely fine! Another highlight was La Speranza, a gorgeous deli serving excellent coffee, pastries, cheese, and wine. They kindly spoke English when we got stuck and made us feel so welcome.

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 :)

Antico Borgo Ripostena – n. 8 Old House
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 :)

Country house with panoramic pool and gardern
This is a fabulous house. While we were there we had not so great weather so a lot of the outdoor space went unused but we did have one evening that it was nice enough to sit outside and over look the valley. This is a house that is not walkable to anything. We would say they "live in the country". We didn't have an issue with this since we had hired a driver but be aware that there is nothing close by. The owners were so responsive and so kind during check in. Couldn't have asked for better owners.
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.

Loggiato 3 apartment in Tuscany near Siena
We had a great stay in Francesca's agriturismo. beautiful place with breath taking views. the place was very clean and tidy and it had all we needed and much more. it was a good base for traveling the area. take a ride on the SP146 - you won't regret it! all in all this place is highly recommended! wish i would visit here again. Toscany is soo beautiful.

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 immediately fell in love with this property. Everything here makes up the image that can be made 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 there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!

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.

La Casetta
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, ...)

Poggiolieto Studio - on hills 10' from city center
We had a lovely a time at the property. It was exactly as described and had amazing views. The host was very welcoming and was exceptionally helpful. It is fairly easily to get to the city centre from the property. There are two fairly regular buses and we were able to use a maps app pretty successfully to predict travel times.
Home rentals with a private pool

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.

Villa Alba by Interhome
Pierluigi and his wife have built a beautiful home in the San Gimignano hills. We had a perfect week with our family there. The house and gardens have gorgeous views over the vineyards and olive groves, and we woke to bird song every morning. The place is spotlessly clean and felt like a home away from home, with all the amenities you could need. The town is a short drive away and is stunning, with great restaurants and things to see and do. The road leading to the villa is rough and steep, however it is worth it for the peace, quiet, privacy and views. Pierluigi and his wife welcomed us in person and they are the loveliest people. He was helpful and responsive throughout our stay via text. We will return!

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

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
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.
Wp Relais Villa Vignalunga
Family of 5 here, 3 small kids. A wonderful stay! We toured surrounding villages in the morning and came back to the pool to beat the heat in the afternoon. The private cooking class with Valentina was the absolute highlight of the trip!
Quick stats about vacation rentals with a pool in San Gimignano
Total rentals
530 properties
Nightly prices starting at
G$2,092 GYD before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
240 properties allow pets
Rentals with dedicated workspaces
130 properties have a dedicated workspace
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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
- Things to do San Gimignano
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- Things to do Province of Siena
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