
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
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.

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.

Countryside house with private pool and garden
Such an amazing place! I would recommend EVERYONE to go there! Violante and her husband are such nice hosts. We had a wonderful time there and will not hesitate to come back next year. Thanks a lot.

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

"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
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. 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
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,

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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- Duomo di Firenze
- Ponte Vecchio
- Teatro Verdi
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- CavallinoMatto
- Uffizi Gallery
- Parco delle Cascine
- Marina di Grosseto beach
- Mercato Centrale
- Basilica di Santa Croce
- The Boboli Gardens
- Stadio Artemio Franchi
- Pitti Palace
- Piazzale Michelangelo
- Kite Beach Fiumara
- Santa Maria della Scala
- Piazza della Repubblica
- Teatro della Pergola
- Palazzo Vecchio
- Podere La Marronaia, Sosta alle Colonne
- Palazzo Medici Riccardi
- Avignonesi Winery Fattoria Le Capezzine
- Things to do Province of Siena
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