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Vacation rentals with a pool in Casole d'Elsa

Find and book unique homes with a pool on Airbnb

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Popular amenities for Casole d'Elsa rentals with a pool

House rentals with a pool

Top guest favorite
Home in Barberino Tavarnelle
5 out of 5 average rating, 108 reviews

Infinity pool in Chianti area

KrisRating, 5 stars2 weeks ago
"Perfect" is the only word that comes to mind for Anna's place. Such a serene location and perfect for a family. The view is just spectacular. We felt so at home and loved sitting out in the yard and by the pool. Anna provided us with a list of so many amazing things to do/see near and far. A must do is the pasta making with Vilma at the house-the most memorable and delicious meal from our trip! Can't wait to go back there to live more of the Tuscan life and enjoy the most beautiful view. Thank you, Anna, for hosting such a gem!
Guest favorite
A spacious outdoor pool is surrounded by lush greenery, featuring olive trees and vibrant plants. The pool's crystal-clear water reflects the sky, while a sun terrace with lounge chairs is available for relaxation. The serene landscape enhances the tranquil atmosphere of the setting.
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 favorite
A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.
Home in San Miniato
4.93 out of 5 average rating, 134 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars2 weeks ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
Superhost
A large swimming pool is set amidst lush greenery, featuring a terracotta border. The pool reflects the clear blue sky, and gentle hills can be seen in the background, offering a peaceful view of the surrounding landscape.
Home in Figline Valdarno
4.96 out of 5 average rating, 108 reviews

The Owl: view, pool and garden

JasonRating, 5 stars4 weeks ago
What a great place to stay while visiting Tuscany. The home is a renovated medieval watchtower located up a dirt road, tucked on a hilltop overlooking the valley. Jacopo, the host, was so kind, hospitable and responsive during our 5-day visit. Would definitely recommend this place to explore Tuscana.
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
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 favorite
Aerial view of a rustic stone house surrounded by greenery and olive trees. A rectangular pool is visible, with turquoise water and purple umbrellas shading lounge chairs. The expansive garden features lush grass and landscaped foliage, providing a serene and spacious outdoor environment.
Home in Volterra
4.93 out of 5 average rating, 180 reviews

Collina Power

DeanRating, 5 stars3 weeks ago
Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!
Guest favorite
An open natural swimming pool is surrounded by lush greenery, featuring wooden lounge chairs positioned along the poolside. The tranquil water reflects the surrounding landscape, while a gentle waterfall can be seen emerging from one end, enhancing the serene environment.
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!!!
Guest favorite
A rectangular private pool is surrounded by a grassy area and olive trees, providing a serene outdoor setting. Six lounge chairs are placed neatly around the pool, offering space for relaxation. The sky is partly cloudy, enhancing the natural beauty of the surroundings.
Home in San Miniato
4.92 out of 5 average rating, 104 reviews

Lovely house in a scenic and paiceful location

BiancaRating, 5 stars6 days ago
We enjoyed Maria's great house. We were kindly welcomed by Maria and her family, where we were welcomed with a bottle of wine and delicious cake. We were with 6 adults. There's plenty of room. It's nice that every bedroom has its own bathroom. It is a beautiful house in a beautiful area with a wonderful swimming pool between the olive trees and it is really equipped with every comfort. Very nice is also the charger for the electric car. We picked up fresh bread every morning from the local baker in the village 5 minutes away by car. Good base for the beautiful cities such as Lucca, Siena, Florence. The beach is also great. We felt very much at home. Maria and family, thank you for the great time in your beautiful home.

Condo rentals with a pool

Guest favorite
A small outdoor table is set for two on a private terrace, featuring a mosaic surface. Two glasses of red wine and a plate of snacks sit on the table. The view includes rolling hills, olive trees, and distant homes, creating a serene countryside backdrop.
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.
Guest favorite
A swimming pool is foregrounded with vibrant red roses, offering a striking contrast against the clear blue water. The panoramic view features rolling hills and the medieval towers of San Gimignano in the distance, with sun loungers arranged around the pool area.
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.
Guest favorite
An exclusive outdoor area features a small wooden pool surrounded by a sun deck. Two colorful lounge chairs in red and blue are positioned nearby, complemented by lush greenery and olive trees, creating a serene natural setting.
Condo 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 favorite
Condo 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
A serene outdoor area features a swimming pool with clear blue water, bordered by wooden decking. Four lounge chairs face a vibrant garden of yellow flowers, offering expansive views of the surrounding hills and sky filled with fluffy clouds.
Condo 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 immediately fell in love with this property. Everything here makes up the image that can be made 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 there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!
Guest favorite
Condo 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.
Top guest favorite
A scenic view is captured from a balcony, showcasing rolling green hills under a partly cloudy sky. Trees and shrubs frame the foreground, while stone rooftops imply a rustic structure nearby. The landscape extends towards distant mountains, enhancing the natural beauty of the area.
Condo in Castellina in Chianti
4.92 out of 5 average rating, 60 reviews

Apartment with terrace and stunning view

LeonRating, 5 stars2 weeks ago
Staying at Raisa's was incredibly nice. The accommodation and especially the view is much nicer than shown in the pictures. Raisa went to great lengths to make everything as pleasant as possible for us. The dogs (Saila and Yango) are mega cuddly, the pool is great and the whole property is really picturesque. By car, beautiful city trips, etc. are easily doable and we would be happy to come back again sometime.
Guest favorite
A tranquil seating area is framed by lush greenery, featuring two wooden lounge chairs positioned on a stone pathway. A serene swimming pool is visible in the background, reflecting the surrounding landscape and sunlight.
Condo in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviews

Orgiale Charme Residenz Castle

ShellRating, 5 stars1 month ago
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!

Home rentals with a private pool

Guest favorite
Home in San Casciano Val di Pesa
5 out of 5 average rating, 5 reviews

Sole by Interhome

MarkRating, 5 stars2 weeks ago
Incredible host. Incredible house. You feel like you are inside a postcard. The most beautiful views are all around you. We did not want to leave. Just breathtaking.
Guest favorite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
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!
Top guest favorite
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.
Superhost
A sunlit infinity pool is surrounded by a stone terrace adorned with comfortable lounge chairs and umbrellas. The tranquil landscape of rolling hills and trees extends in the background, complementing the rustic charm of the stone cottage structure.
Home in Pescia
4.86 out of 5 average rating, 21 reviews

Aurora by Interhome

NatalieRating, 5 stars3 weeks ago
We had a lovely week at this place. In particular, the outdoor area was fantastic! Thank you and happy to come back!
Top guest favorite
A serene outdoor pool is surrounded by manicured grass and lush vineyards. Two lounge chairs are positioned under a shaded structure, offering a comfortable seating area, while the crystalline water of the pool glistens in the sunlight.
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 favorite
A spacious room features polished black and white marble flooring, with large arched windows allowing natural light to fill the space. A glass-top table is elegantly set with decorative glassware, while a cozy seating area with a light-colored couch complements the tranquil ambiance.
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 favorite
A bright living area is highlighted by a white sectional sofa, complemented by red throw pillows. An elegant area rug sits on terracotta tiles, with wooden beams and a staircase leading to the upper level visible. Light streams through a window, enhancing the warm atmosphere.
Home in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 97 reviews

Casa Luigi Suite with exclusive pool

DerekRating, 5 stars2 days ago
I looked at dozens of other ABBs before choosing Giovanna's place and I know I made the best choice after staying. The setting is absolutely beautiful and peaceful. Lounging at the pool was so nice. We had the pool all to ourselves which is hard to find with other ABBs. The home is a nice large space and very clean. The views out the window are great. Giovanna was so nice and welcoming just a wonderful person. We enjoyed having a drink with her and Luigi. I highly recommend her place.
Guest favorite
The image showcases a charming house nestled among lush vineyards, with rolling hills stretching into the distance. A private swimming pool is visible beside the home, surrounded by sun loungers. The vibrant greenery reflects a serene countryside atmosphere, emphasizing the property's picturesque location.
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 vacation rentals with a pool in Casole d'Elsa

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$12,553 GYD before taxes and fees

  • Total number of reviews

    260 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Casole d'Elsa
  6. Rentals with pools