
Holiday 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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House rentals with a pool

Casa Fattore - Tuscan countryside house
We had a wonderful stay at this property which is a bit difficult to reach, but is more than worth the painstaking arrival. The fantastic location is simply breathtaking – expansive fields lined with cypresses and olive trees create a backdrop that looks like a Tuscany picture book. The hosts were extremely nice and charming. They provided us with great tips for excursions and activities in the area, which has enriched our stay. Particularly noteworthy is that our dog also felt very comfortable and we could thus enjoy relaxing time as a family. In summary, we can recommend this place to anyone who wants to experience the true beauty of Tuscany. A place to relax and enjoy – here we will be happy to come back.

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

Tuscan Villa Poggetto Montalcino
Villa poggetto was a beautiful and quiet retreat. Our family used it as a base for seeing other parts of Tuscany and hired a car so it was perfect. It has basic amenities and the pool is in great condition. Only critique is the doors don’t lock well (not really a concern as the area is quiet) and as it is rural there are animals around such as mice and cute local cats. Gastone was a great host who allowed us to check in at 11pm when we were running late. He is very responsive and kind.

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 had a great stay for 2 nights when traveling to Sicily. Barbara and Gigi were very welcoming. The house was great, it was private, clean and spacious with a great interior. Our dog could walk freely in the garden. The pool was clean and used multiple times during the day.

"Casa Elisa", house with swimming pool at the foot of Cortona
I had an unforgettable stay at Casa Elisa, located at the foot of beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary amenities. The garden with swimming pool is an oasis of tranquility, ideal for relaxing with a good book or enjoying a sunset aperitif. But it is the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information on places to visit and recommended restaurants makes a difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.
Condo rentals with a pool

Adalberto Apartment inside the Manor of Fulignano
Amazing. Giovanni was helpful when we couldn’t stay night one and went above and beyond to help us secure a refund. Highly recommend.

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
Very peaceful and beautiful stay!!

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.

Casa del Noce
An enchanting place surrounded by nature, with free horses that make the atmosphere magical and relaxing. The farmhouse is cared for and welcoming, and the people who welcomed us were of a unique kindness. A perfect place to disconnect and rejuvenate.

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
Amazing place to stay if you want peace and quiet! We booked here to break up our highly adventurous, active trip where there was a lot of night life. There are a few fantastic restaurants and bars in the area to go to and the views are very nice. It’s very clean and the bathroom tub and shower are super. The pool was not open because we came little too early in the season but the view and peacefulness was stunning there as well. Highly recommend for anyone who wants peace and quiet!

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!!
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
Emanuela and Giovanni were wonderful hosts! The villa was beautiful. Everything was wonderful. We felt right at home. The scenery was incredible. The garden and pool were wonderful. They left us essentials to get us started like coffee, milk, bread and a bottle of wine. Kitchen had everything we needed. Located in the heart of Chianti. Overall, it was excellent. Highly recommend!

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. For excursions to the well-known area with San Gimignano, Volterra, Siena, Florence, etc., an ideal starting point. Highly recommended

Explore nature in the center of Vigneti Chianti
Absolutely loved our family stay at Rita’s place. It was such a perfect spot - location was amazing! So clean! We can’t wait to be back xo

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,

Casa la Selvolina, by Interhome
La Selvolina is a great place to unwind and enjoy the surroundings, but also the lovely pool. The house is nice, the kitchen very complete. Everything is available for a wonderful stay. If you have any questions, there was always a quick and very friendly response, which we experienced as very pleasant and welcome. La Selvolina is a wonderfully quiet place, about a 30 minute walk (up the mountain) or 5 minutes by car to Roccastrada. If you're lucky, you could see deer in the garden and hear the owls at night. It is advisable to have an SUV because the road is not paved.
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Uffizi Gallery
- CavallinoMatto
- Piazzale Michelangelo
- Parco delle Cascine
- Mercato Centrale
- Marina di Grosseto beach
- Piazza della Repubblica
- Pitti Palace
- Stadio Artemio Franchi
- Kite Beach Fiumara
- Giardino Bardini
- The Boboli Gardens
- Cavallino Matto
- Avignonesi Winery Fattoria Le Capezzine
- Santa Maria della Scala
- Casa Barthel
- Things to do Province of Siena
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