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Holiday rentals with a pool in Asciano

Find and book unique homes with a pool on Airbnb

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Popular amenities for Asciano rentals with a pool

House rentals with a pool

Guest favourite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
Guest favourite
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Old House

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 :)
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 138 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)
Top guest favourite
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!
Superhost
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars1 month ago
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always received good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he could move freely. We would come back. It was an incredibly beautiful time!
Guest favourite
Home in Rigomagno
4.96 out of 5 average rating, 100 reviews

House Rigomagno Siena

Marco JustusRating, 5 stars1 week ago
We had a wonderful time in this absolutely cute house, which is surrounded by breathtaking nature. The tranquility is unique - you can only hear the chirping of the birds, and every now and then deer appear at the edge of the forest. Simply magical! The pool was well maintained and you had real peace. A real highlight for us was the kitchen: so lovingly furnished and exceptionally well equipped - we have never experienced anything like it! The gas stove and the high-quality oven have made cooking a pleasure. Host Diego was incredibly friendly, attentive and warm. You immediately feel welcome and well cared for. A perfect retreat for those who appreciate nature, tranquility and loving details.
Superhost
Home in Anghiari
4.88 out of 5 average rating, 140 reviews

Tuscan dream in the ancient Tobacco's villa, sauna

JacquelineRating, 5 stars1 month ago
The house is beautiful and unlike anything else. What made the experience amazing was one of the hosts, Daniela. Daniela greeted us upon check in, walked us around the house and went above and beyond and booked us a wine tour where he graciously translated everything in English during the entire experience. Daniela made the place feel like home and I couldn’t recommend him and the experience he provides more.
Guest favourite
Home in Certaldo
4.91 out of 5 average rating, 130 reviews

Paluffo Stillo House

LeahRating, 5 stars3 weeks ago
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!

Apartment rentals with a pool

Guest favourite
Apartment 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.
Superhost
Apartment in San Gimignanello
5 out of 5 average rating, 12 reviews

L'Oliviera, 2 bedrooms stylish apartment

AnaRating, 5 stars5 days ago
Amazing Airbnb and wonderful location! Such a gem!
Guest favourite
Apartment 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.
Guest favourite
Apartment in Figline e Incisa Valdarno
4.93 out of 5 average rating, 472 reviews

Casa Rebecca with a small private pool

MuskanRating, 5 stars2 weeks ago
Benedetta is an amazing and gracious host, the property was easy to locate and the room was beautiful, absolutely amazing Tuscan style with beautiful views and a private pool. She also recommended us a restaurant for dinner and that was one of the beat meals we had in Italy! 100% recommend
Guest favourite
Apartment in Rifredi
4.92 out of 5 average rating, 167 reviews

VILLA LE PERGOLE - Florence

JennaRating, 5 stars1 week ago
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.
Superhost
Apartment in Castelfranco di Sopra
4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars1 week ago
We were immediately enchanted by this property. Everything here makes up the image that one can have of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good right away, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!
Guest favourite
Apartment in Sesto Fiorentino
4.95 out of 5 average rating, 100 reviews

Ginestra: Private Pool Overlooking Florence

LauraRating, 5 stars2 months ago
Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.
Guest favourite
Apartment in Casole d'Elsa
4.93 out of 5 average rating, 157 reviews

La Casetta

RalfRating, 5 stars3 weeks ago
We can absolutely recommend it! Everything is as described in the text and as shown in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information for the journey and many great tips on site, always with the corresponding links. For example, our arrival was delayed to about 10:15 pm due to traffic. Was no problem, we were in contact and when we arrived, Andrea personally received us. And if we had a question during our stay, an answer always came very quickly. (Where is the best place to park in Siena, how do you best get to Florence, ...)

Home rentals with a private pool

Guest favourite
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 favourite
Home in Civitella Paganico (GR)
4.95 out of 5 average rating, 22 reviews

Podere Vignali by Interhome

GeorginaRating, 5 stars2 weeks ago
Our stay at Podere Vignali was amazing. Our hosts were friendly and generous and nothing was too much trouble. It was private and beautiful and felt like a home away from home.
Top guest favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Explore nature in the center of Vigneti Chianti

BaileyRating, 5 stars1 week ago
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.
Guest favourite
Villa in San Miniato
4.85 out of 5 average rating, 41 reviews

Historic home with exclusive pool

AylaRating, 5 stars11 months ago
We (7 friends) enjoyed staying at the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She sent us a lot of tips about the area (including the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed something, an answer came very quickly. The villa is well equipped and the surroundings are beautiful. There is plenty of parking space. Only the potholes and the access to the villa are a bit challenging - but doable!
Top guest favourite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 47 reviews

Charming villa in the Chianti hills

JessicaRating, 5 stars1 week ago
We stayed in the villa for 3 weeks with my family (2 young kids) and it was absolutely perfect!!! Francesca was an incredible host, fantastic communication. The house itself was beautiful, clean and the pool was just magic. Close to Florence and all the wonderful towns nearby, we can’t recommend this place enough. Would stay again without hesitation.
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars9 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Guest favourite
Home in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 96 reviews

Casa Luigi Suite with exclusive pool

KatieRating, 5 stars3 weeks ago
We had an amazing stay here! The property is beautiful: great views, flowers and lemon/orange trees were blooming, and the pool was great plus super clean! The bnb was cozy with traditional Tuscany vibes. Giovanna and Luigi were amazing! Super friendly, loving, helpful, and funny 😁 highly recommended if you're looking for a peaceful country setting!
Guest favourite
Home in Greve in Chianti
4.96 out of 5 average rating, 28 reviews

Casa 360 by Interhome

AnneRating, 5 stars1 month ago
I cannot say enough about how much we loved this place! The house is adorable, the views are spectacular and Borgo Savignola wine is outstanding! We were lucky enough to have Luzius prepare 2 dinners for us and they were both amazing. My family and I had a wonderful stay and truly hope to go back!

Quick stats about holiday rentals with a pool in Asciano

  • Total rentals

    510 properties

  • Nightly prices starting at

    ₹4,319 before taxes and fees

  • Total number of reviews

    6.3K reviews

  • Family-friendly rentals

    320 properties are a good fit for families

  • Pet-friendly rentals

    240 properties allow pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

Destinations to explore

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