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Holiday rentals with a pool in Province of Siena

Find and book unique homes with a pool on Airbnb

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Popular amenities for Province of Siena rentals with a pool

House rentals with a pool

Guest favourite
Home in Civitella in Val di Chiana
4.93 out of 5 average rating, 46 reviews

Casa Fattore - Tuscan countryside house

MarciaRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Gavorrano
5 out of 5 average rating, 11 reviews

Pirite Dependance Agriturismo La Miniera (swimming pool)

HélèneRating, 5 stars7 months ago
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
Superhost
Home in San Giovanni d'Asso
4.77 out of 5 average rating, 52 reviews

Tuscan Villa Poggetto Montalcino

SamRating, 5 stars7 months ago
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.
Superhost
Home in Ville
4.79 out of 5 average rating, 29 reviews

Independent Tuscan Villa Siena with Pool (7+1)

RonRating, 5 stars7 months ago
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.
Top Guest favourite
Home in Serre di Rapolano
4.97 out of 5 average rating, 74 reviews

L'Olivo - detached villa with swimming pool

MartaRating, 5 stars7 months ago
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.
Guest favourite
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars7 months ago
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!
Top Guest favourite
Home in Arezzo
5 out of 5 average rating, 33 reviews

Beautiful barn among the olive trees

TijmenRating, 5 stars1 week ago
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.
Guest favourite
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", house with swimming pool at the foot of Cortona

AlessandroRating, 5 stars4 months ago
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

Top Guest favourite
Condo in San Gimignano
4.95 out of 5 average rating, 125 reviews

Adalberto Apartment inside the Manor of Fulignano

SpencerRating, 5 stars1 week ago
Amazing. Giovanni was helpful when we couldn’t stay night one and went above and beyond to help us secure a refund. Highly recommend.
Superhost
Condo in Sovicille
5 out of 5 average rating, 3 reviews

2-bedroom and 2-bathroom apartment, kitchen, pool

MilanRating, 5 stars93 months ago
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.
Guest favourite
Condo in Radda in Chianti
4.84 out of 5 average rating, 88 reviews

💜 "Gaia" at Podere Le Fontanelle

Urte AruneRating, 5 stars1 week ago
Very peaceful and beautiful stay!!
Superhost
Condo in San Gimignano
5 out of 5 average rating, 4 reviews

Apartment Melissa

StéphanieRating, 5 stars83 months ago
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.
Superhost
Condo in Lucignano
5 out of 5 average rating, 3 reviews

Casa del Noce

AlessiaRating, 5 stars1 week ago
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.
Superhost
Condo in Castellina in Chianti
4.77 out of 5 average rating, 236 reviews

The house in Chianti - IlVillinoFarmhouse

AngelinaRating, 5 stars6 months ago
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.
Superhost
Condo in Montefollonico
4.88 out of 5 average rating, 58 reviews

Il Chicchino, Swimming Pool, Tennis, Wi-Fi, Park

TravisRating, 5 stars3 days ago
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!
Superhost
Condo in San Gimignanello
5 out of 5 average rating, 5 reviews

Il Loggiato, 2 bedrooms with a view

LaurenRating, 5 stars7 months ago
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

Home in Castiglion Fiorentino
5 out of 5 average rating, 3 reviews

La Felcaia by Interhome

JenRating, 5 stars8 months ago
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!
Guest favourite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 189 reviews

Stone House with Exclusive Pool Codilungo in Chianti

JacquelineRating, 5 stars2 days ago
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!
Guest favourite
Home in Civitella Paganico (GR)
4.94 out of 5 average rating, 18 reviews

Podere Vignali by Interhome

SimoneRating, 5 stars7 months ago
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.
Home in Poggibonsi
4.4 out of 5 average rating, 5 reviews

The Nest by Interhome

MartinRating, 5 stars11 months ago
"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
Top Guest favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 225 reviews

Explore nature in the center of Vigneti Chianti

MelissaRating, 5 stars6 days ago
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
Home in San Gimignano
4.75 out of 5 average rating, 4 reviews

Villa Alba by Interhome

BernieRating, 5 stars31 months ago
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.
Home in Pieve a Presciano
5 out of 5 average rating, 3 reviews

Casavecchia by Interhome

NickRating, 5 stars19 months ago
Great holiday typical Toscan atmosphere.I strongly recommend,
Home in Roccastrada
4.92 out of 5 average rating, 13 reviews

Casa la Selvolina, by Interhome

IrisRating, 5 stars7 months ago
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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