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Vacation 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 favorite
Home in Buonconvento
4.97 out of 5 average rating, 87 reviews

S.Ilaria - Private pool Villa with 2 bedrooms

AlisonRating, 5 stars3 weeks ago
Fabulous setting in the middle of fabulous Tuscany. The views from the house were stunning! The farmhouse itself was so charming - every detail. We enjoyed dinners on the covered patio, evening walks on the gravel road through the countryside and lounging by the pool with a glass of red wine. The setting is also the perfect location for day trips to nearby cities. We visited Montalcino, Montepulciano, Siena, Pienza and Cortona. Highly recommend!
Guest favorite
Home in Arezzo
4.9 out of 5 average rating, 167 reviews

Interno Italiano

LloydRating, 5 stars8 months ago
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!
Top guest favorite
Home in Barberino Tavarnelle
5 out of 5 average rating, 109 reviews

Infinity pool in Chianti

VeerleRating, 5 stars6 days ago
Dear Anna, nu we bijna terug een week in België zijn, dringt het nog meer tot ons door hoe prettig het verlof was in Toscane. Ik wil je hartelijk danken voor je goeie zorgen en betrokkenheid. We hebben zo genoten van je mooie huis -waar alles aanwezig was-, het mooie zwembad en de prachtige wijnhuizen en steden in de buurt. Ik wil je ook een dik compliment geven voor je prachtige planten op het hele domein. Het is niet simpel om die zo gezond te houden onder de Italiaanse zon. Kortom, ik zal je huis aan iedereen aanbevelen en wens je nog veel succes met de werken in het nieuwe, naburige huis. Veel groetjes aan je echtgenoot en zoon. Baci Veerle & co
Guest favorite
Home in Cavriglia
4.93 out of 5 average rating, 80 reviews

Wonderful country house

MichaelRating, 5 stars1 week ago
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.
Guest favorite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

LéaRating, 5 stars6 days ago
Nous avons adoré notre séjour chez Bernardino ! Le paysage est magnifique, l’endroit est très propre et la piscine est un vrai plus pour se détendre. Bernardino est un hôte attentionné, toujours à l’écoute et prêt à aider à tout moment. Merci pour cette belle expérience !
Top guest favorite
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!
Guest favorite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 138 reviews

Casa di Lyndall - Entire house with exclusive pool

SilvanRating, 5 stars4 days ago
Wir hatten eine wunderbare Woche in Lyndalls Haus in Lecchi in Chianti! Das Grundstück, das Haus und der Pool waren sogar größer und schöner als erwartet. Die Landschaft ist traumhaft – perfekt zum Entspannen. Die Küche war hervorragend ausgestattet, sodass wir fast jeden Tag gekocht haben. Auch die Restaurant-Empfehlung im Ort war ein Volltreffer. Wir haben uns rundum wohlgefühlt und würden jederzeit gerne wiederkommen. Vielen Dank, Lyndall!
Guest favorite
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Casa Vecchia

LucyRating, 5 stars2 weeks ago
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 :)

Condo rentals with a pool

Guest favorite
Condo in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment

TomRating, 5 stars2 weeks ago
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.
Top guest favorite
Condo in San Rocco a Pilli
5 out of 5 average rating, 40 reviews

Traditional Apartment with Patio and Garden View

KeithRating, 5 stars3 weeks ago
Pierre, Eric and family have created an amazing place to stay. From the warm welcome on arrival and dinner with them the next night, a week was not enough time spent there. They have really created a beautiful place to stay and we look forward to staying again.
Top guest favorite
Condo in Buonconvento
5 out of 5 average rating, 24 reviews

Cottage 48 mq, piscina, relax, immerso nel verde

NaumanRating, 5 stars9 months ago
Had an amazing time with Sara & Simone - truly the best hosts we've come across. The place was fantastic, amazing views by the pool, great room, clean and all the amenities needed are available. Sara & Simone are great hosts, they made us breakfast one day which was amazing, fresh organic food with the best view. And all their local recommendations and reservations made our trip in Tuscany much nicer. Can't wait to come back again 👌
Guest favorite
Condo in Castellina in Chianti
4.95 out of 5 average rating, 39 reviews

Il Giaggiolo - Chianti with a view

AmeliaRating, 5 stars3 weeks ago
We stayed in Monica’s home for five nights and four days, and it was incredible. The second we checked in Monica sent me an extensive list of instructions and places to visit during our stay. My favorite list was restaurants and local food shops in the area she recommends as a local. The house had all the amenities you could need/want, comfortable beds, and a really nice patio area. We are a few meals outside and enjoyed the stunning view. We saw some of the most beautiful sunsets as well. The pool was really well kept. There were many wineries the were nearby. The location was also great for taking day trips to Florence and Siena. The nearest town was so cute and had a lot of nice shops and restaurants. We are so appreciative of Monica’s food recommendations and suggestions of things to do. Overall we had an amazing time, and we highly recommend staying here!!
Guest favorite
Condo in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars1 month ago
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.
Superhost
Condo in Castelnuovo Berardenga
5 out of 5 average rating, 5 reviews

San Rocco - Bellavista - Castello di Bossi

GaiaRating, 5 stars10 months ago
La struttura è meravigliosa, immersa nel verde e con una piscina dalla vista incredibile. La camera era pulitissima e con tutti i comfort possibili. Abbiamo interagito molto con una gentilissima signora della reception, molto cordiale e disponibile. Il vino che abbiamo degustato inoltre era eccezionale , vale la pena soggiornarci anche solo per una notte! Estremamente raccomandato
Top guest favorite
Condo in Cinigiano
5 out of 5 average rating, 92 reviews

Appartamento Spinosa a Podere Capraia

FlorianRating, 5 stars2 weeks ago
We had a wonderful time at Alberto‘s and Laura‘s - it turned out that we didn’t do as many trips into the surroundings as planned because we just wanted to enjoy the beauty of the garden and the amazing views. It was the perfect ending of a fantastic vacation in Italy - I hope we will be back next year :) We received a fantastic welcome, home made bread, jam and pasta - and immediately felt like home. Grazie! One thing to mention is that the apartment is kind of thin-walled towards the second apartment - that didn’t bother us at all, but might be of interest for fellow travellers who are sensitive to noises. All in all, certainly one of the best accommodations we have stayed in!
Top guest favorite
Condo in Montieri
5 out of 5 average rating, 49 reviews

PodereCupiano "la Costa"

KatjaRating, 5 stars1 week ago
Wir haben uns wirklich sehr wohl gefühlt! Francesco ist ein herzlicher und ganz toller Gastgeber. Die Anlage ist traumhaft schön und es ist so ruhig. Wir würden jederzeit wieder kommen

Home rentals with a private pool

Home in Pergine Valdarno
4.67 out of 5 average rating, 6 reviews

Il Forno by Interhome

KorbinianRating, 5 stars2 weeks ago
Ein sehr schönes Haus mit traumhafter Aussicht. Der Pool war perfekt. Es waren genug Liegen und Stühle vorhanden. Der Vermieter Antonio ist ein sehr netter und hilfsbereiter Mensch. Die Weinprobe im Castello di Montozzi war ein Traum! Wir können die Unterkunft nur weiterempfehlen! ☺️
Guest favorite
Cottage in Barberino Tavarnelle
4.97 out of 5 average rating, 193 reviews

Stone House with Exclusive Pool Codilungo in Chianti

SarahRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Civitella Paganico (GR)
4.96 out of 5 average rating, 23 reviews

Podere Vignali by Interhome

LaraRating, 5 stars4 days ago
We had a wonderful stay! The house is perfect for larger groups or families – everyone having their own bathroom was a real plus. It was very clean and well maintained, and the pool area was lovely and well cared for. The kitchen is well equipped, and the property overall offers plenty of space to relax. The surroundings are beautiful and peaceful – we spotted fireflies at night, heard owls, and even saw a porcupine! A true nature experience. We received great tips from the host’s father. Carlo and Giovanna were always very kind and helpful. Communication with the host was smooth and friendly throughout. The house is a great base for exploring the area, though you do need a car to reach most shops – the little store in Pari is charming but quite small. The road to the house is a bit bumpy, but manageable. All in all, a great place to unwind and enjoy time with family and friends. Thank you for everything!
Home in Civitella in Val di Chiana
4.88 out of 5 average rating, 24 reviews

Casa Clotilde by Interhome

DidierRating, 5 stars2 weeks ago
Nous avons passé un agréable séjour à la Casa Clotilde dans un environnement calme et reposant. La maison et le jardin avec la piscine ont été fortement appréciés par nous tous. Une belle vue sur les collines de Toscane et de belles randonnées à faire aux alentours. Merci pour cette semaine sous le soleil.
Home in San Gimignano
4.8 out of 5 average rating, 5 reviews

Villa Alba by Interhome

ParisaRating, 5 stars1 month ago
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!
Guest favorite
Home in Cortona
4.83 out of 5 average rating, 18 reviews

Il Loto by Interhome

DavidRating, 5 stars1 week ago
We had a great stay at the villa! Diego and Aldo were great hosts and were very responsive to any issues we had. There was a slight issue with the water but both of them were able to quickly help and were extremely kind. Would definitely recommend!
Home in Castiglione d'Orcia
4.67 out of 5 average rating, 30 reviews

Casa Frati by Interhome

JoJoRating, 5 stars2 weeks ago
Overall the location and charm of the property were stunning. Spacious bedrooms and living areas (beware uneven flooring, to be expected in an old farmhouse, my elderly father struggled). NOTE: we have not been asked for a cash deposit with Airbnb before and were surprised when a man came about 3 hours after we arrived to collect €400 cash. He spoke no English and used his phone to call someone who could speak to me. The host had not said he would be coming, or who he was. I contacted Airbnb support who said I could pay through the resolution centre. As others mentioned, there were no oil, salt, pepper etc, although a few dishwasher tablets. The jacuzzi and sauna work with tokens for €8 each. Didn’t use so not sure how long you get. BUT, this is a stunning property with unbeatable views in the heart of Tuscany, tucked away on a hillside down a gravel track. Would definitely book again. Pool is pristine, towels spotless, beds comfortable.
Guest favorite
Villa in Castiglione d'Orcia
4.95 out of 5 average rating, 102 reviews

Wp Relais Villa Vignalunga

MatthewRating, 5 stars1 week ago
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!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Rentals with pools