
Vacation rentals with a pool in Province of Siena
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Top-rated rentals with a pool in Province of Siena
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Popular amenities for Province of Siena rentals with a pool
House rentals with a pool

Casa Fattore - Tuscan countryside house
The stay at the Capocontro estate was very satisfying. The entire ancient hamlet is a jewel set in the countryside, with spectacular views of the woods of Val di Chiana. The accommodation is tidy and clean, picturesque and elegantly retro. Piero and Lella were very helpful in communications and suggestions for places to visit and where to eat. We loved the peace and quiet of the place, as well as the pool with a view. We stopped for a short time and the weather was a bit capricious, otherwise we would have enjoyed the farm's outdoors more. The only small flaw: the dishes and the fridge were not exactly immaculate, but nothing that can't be solved with a sponge. Super recommended for both a short and a long stay, so you can enjoy the quiet of the place and visit the surrounding area.

Casa Belvedere with Pool
The photos do not capture beauty and character of this place. Very comfortable and high spec renovation of the historic farmhouse ... spacious, relaxing, huge pool, bedrooms stayed cool even as temperature reached 30+ degrees. Great restaurant just round the corner, and top wineries nearby. Fantastic weekend was had, thank you Maurizio!

Pirite Dependance Agriturismo La Miniera (swimming pool)
Nice little house in a very large enclosed yard with a beautiful house in front with several rentals. Functional, enough to cook in terms of utensils. Provide extra bath towels for the pool. Nothing is closed or locked outside between rentals (ideal place to organize a family stay, family reunion or with friends, the setting is so ready) with this beautiful swimming pool (totally fenced for security) plenty of space around, it's not disturbing if there are several people, deckchair, it is cleaned every day. Very green setting with farm animals (ponies, donkeys, pigs, cow and her calf, etc.) nearby and wild boars. Just for info it's nestled, no view but rejuvenating because in nature. We did not meet Giancarlo who is very responsive to messages but we met his son with his small family who are very friendly, give advice and information, they like to exchange. Thank you all

Independent Tuscan Villa Siena with Pool (7+1)
We stayed for a week and had a wonderful time. The house is well maintained and exactly as per the description provided. Giovanna and her family are highly responsive and responded instantly to any queries we had. We would highly recommend anyone wanting to go to the Toscana to stay at this wonderful house.

L'Olivo - detached villa with swimming pool
Amazing place in a quiet area with a beautiful view of the countryside. Climate cottage equipped with everything you need. Together with our dogs we felt like at home. Bruna is an incredibly warm and helpful person. Thank you for a wonderful time.

Tuscan farmhouse near Siena + Cortona, heated pool
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!

Beautiful barn among the olive trees
We are delighted with our stay, the house was what we were looking for, authentic exotic, crazy charm

Pasqui Villas :Historic mansion La Consuma
Our stay at Historic Villa La Consuma was unforgettable! The villa combines historic charm with modern comfort, set against stunning Tuscan landscapes. Spacious rooms, elegant decor, and lush gardens make it the perfect escape. Federica, our host, was exceptional—welcoming, attentive, and knowledgeable, adding personal touches that made our stay special. Thanks to her recommendations, we easily explored nearby gems like Montalcino and Montepulciano. For anyone seeking an authentic and luxurious Tuscan experience, Villa La Consuma is a dream come true.
Condo rentals with a pool

Adalberto Apartment inside the Manor of Fulignano
Great stay, incredible views, good location….

2-bedroom and 2-bathroom apartment, kitchen, pool
We received very warm welcome and enjoyed very much Frederica's house, pool, pasta and last but not least Siena , San Galgano and San Gusmo' very much. The place is perfect and I don't remember other spaces from airbnb which can compete with this one. I hope we will be able to come again some time soon.

💜 "Gaia" at Podere Le Fontanelle
It’s the best airbnb we’ve ever been to. Gaia is amazing and she’s very responsive! The place is very clean with magical views. We will be back and recommend this place to family & friends! Very peaceful and very clean! Love it

Apartment Melissa
We stayed in the Melissa apartment and it was great, very spacious and bigger than expected. The apartment is self-catering and has all that you need to cook and have a great time. There is no terrace for this apartment, but they are many areas around the property that allow for some outdoor time. The location was beautiful, amazing views, great swimming pool and an overall very relaxed place. The property is 15 mins away from San Gimignano and very close to the bigger towns/villages to visit. Having a car is a must. The staff, the welcome and overall communication was lovely and easy, I would definitely recommend staying here.

The house in Chianti - IlVillinoFarmhouse
Beautiful structure, everything clean and tidy. We warned that our dog would also come with us and we found a kennel and a bowl in the apartment. Daniela their collaborator in the area was very kind and collaborative. We'll definitely be back.

Il Chicchino, Swimming Pool, Tennis, Wi-Fi, Park
We thoroughly enjoyed our stay at Daphne's place. It is set amongst beautiful manicured gardens, a large pool (which was covered due to seasons end), a tennis court and the views across the Tuscan landscape are incredible. The apartment itself was immaculate and looked better than the photos. It is well appointed, spotlessly clean and modern. We found Montefollonico to be quieter than other tourist destinations and it's a short walk/drive from the residence. It too is beautiful and charming. There's only one Grocery store specializing in Tuscan products and more, It catered for pretty much all we needed. There's also a pharmacy, a quaint bar and a restaurant that was surprisingly good, and the owner is quite the character, in a good way :). Montepulciano is a short 15 or so minute drive away. Having a car is a must unless you just want to spend quality time away from everything and relax in a most beautiful, tranquil and private setting. Thank you Daphne, we loved our stay.

Il Loggiato, 2 bedrooms with a view
Stunning place. Loved the vineyard, olive trees and pool. Exactly what I was looking for in a Tuscan experience!!

Villa Falco-Cignella Resort Apartments in Tuscany
Great peaceful location. Staff is very friendly
Home rentals with a private pool

La Felcaia by Interhome
Luigi and Laura were the perfect host. The vegetables from Laura's family were very welcome. We also loved the dinner they cooked for us. We felt like part of the family. The villa was absolutely amazing. Stunning location, the pool was out of this world. We loved it so much we have already booked for next year!

Stone House with Exclusive Pool Codilungo in Chianti
The Stone House was gorgeous - beautifully and thoughtfully decorated, with amazing views. It was private yet easy to get to many amenities/tuscany towns/wineries nearby. Emanuela and Giovanni were very responsive to our questions and requests. We requested for help to buy a bouquet of flowers to surprise our friend for her birthday on the day we arrive - not only did they take the time to help us buy it, they refused to let us pay for it! it was too cold for us to use the pool but I can imagine how wonderful it would have been if we could have used it. all in all, it was a great place to enjoy a dreamy tuscan holiday.

Podere Vignali by Interhome
Really beautiful place and beautiful surroundings. All communication went smoothly. Very clear instructions and descriptions sf amenities. The host will be in touch with you a few dsge before arrival and check in was super easy.

The Nest by Interhome
"The Nest" in the Localitá Torri is a beautiful place. High-quality, absolutely complete and lovingly furnished. Penibel clean. There was nothing missing at all. There is a lot of passion in the apartment. This fits the owner who did the check in and check out himself. Such a pleasant, nice person. An ideal starting point for excursions to the well-known area with San Gimignano, Volterra, Siena, Florence, etc. Absolutely recommended

Explore nature in the center of Vigneti Chianti
Beautiful place with amazing views! 100% recommend to stay at Rita’s place, definitely recommend!

Villa Alba by Interhome
Casa Alba was fantastic. We had a wonderful stay. We renewed our vows, at Casa Alba, to celebrate our 10 year wedding anniversary & it was a dream day 🤗 Luigi & his wife were there to welcome us & couldn't have been friendlier. My sister, brother in law & their toddler stayed the week with us & I can definitely say we loved it & would absolutely return 🙌 its very close to San Gimignano for everything you could need.

Casavecchia by Interhome
Great holiday typical Toscan atmosphere.I strongly recommend,
Wp Relais Villa Vignalunga
Had the most amazing time in this beautiful place! Stayed for 5 nights, two families with young children, and felt at home once we got there. We were amazed by the design and surroundings. Not enough words to describe!
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- CavallinoMatto
- Uffizi Gallery
- Piazzale Michelangelo
- Parco delle Cascine
- Stadio Artemio Franchi
- Marina di Grosseto beach
- Mercato Centrale
- Piazza della Repubblica
- The Boboli Gardens
- Teatro Verdi
- Pitti Palace
- Basilica di Santa Croce
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Teatro Tuscanyhall
- Palazzo Vecchio
- Kite Beach Fiumara
- Things to do Province of Siena
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