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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

Guest favorite
A private pool area is surrounded by neatly maintained greenery and flowering plants. A wooden sun lounger is positioned near the pool, while a hammock is hung between two trees. Stone stepping stones lead towards the water's edge, creating a tranquil outdoor space.
Home in Florence
5 out of 5 average rating, 12 reviews

The Limonaia della Torretta

GregoryRating, 5 stars1 week ago
A quiet, impeccably furnished heaven. Every need provided for, slept tremendously in the quiet, loved the tiny village two shops and the backyard an oasis from a busy life. Thank you Leonardo. We cannot wait to return.
Superhost
Home in Volterra
4.88 out of 5 average rating, 50 reviews

Tuscan Villa with Privacy,Pool,near towncentre

GaiaRating, 5 stars1 month ago
Paradise environment, in a spectacular setting, very close to the center. House full of all comforts, elegant, perfect for a total relaxing stay. Antonio is always ready to meet your every request, kind, friendly and hospitable. Definitely back!!
Top guest favorite
A private pool is surrounded by lush greenery, with a clear blue sky above. The pool features a shallow entry area, providing an inviting space for relaxation. A well-maintained garden is visible in the background, enhancing the serene outdoor setting.
Home in Pistoia
5 out of 5 average rating, 8 reviews

Country Cottage with Pool "Il Melograno"

FedericaRating, 5 stars9 months ago
Charming villa in total relaxation. Lots of green space and a beautiful pool... all just for us. Giovanni was super welcoming and kind. An experience to repeat, highly recommended! Greetings from Fede and Kevin
Superhost
Home in Montecastelli Pisano
4.92 out of 5 average rating, 38 reviews

Deal 2019 Tuscany Villa le Capanne with pool

PeterRating, 5 stars7 months ago
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.
Superhost
A private swimming pool is surrounded by a wooden deck, offering a serene setting amidst olive trees. Soft water cascades from a shower feature, while a sweeping view of the valley is visible in the background, enhancing the tranquil atmosphere.
Home in San Giuliano Terme
4.88 out of 5 average rating, 77 reviews

Pisa / Lucca-Superb Location-Leaning Tower views!

ChristopherRating, 5 stars1 month ago
As a family of 4, we had a perfect stay at La Lucertola. Luisa and Colin were friendly, attentive and helpful from the minute we arrived to when we left. They were available on the phone throughout, if needed. The music studio was an incredible addition - we felt very lucky to have access to it throughout our stay. The accommodation is located up a narrow track, but this meant we had access to stunning views and wildlife all around. Although the pool was cold, due to the time of year we visited, it didn’t stop us using it a couple of times. The pool is perfectly located - overlooking Pisa. There was plenty of seating around the pool and, although other families were staying in the house next door, it didn’t once feel like we couldn’t use any of the facilities. Other great facilities worth mentioning - the pizza oven is such an experience - to make pizzas overlooking the tower of Pisa, in Italy, was incredible. We also had all the cleaning items and linen we needed too. Grazie.
Superhost
A spacious pool area is featured, surrounded by neatly arranged sun loungers and an umbrella offering shade. The villa's exterior showcases arched openings, providing an inviting view of the pool. Lush greenery and flower beds enhance the tranquil setting under a clear blue sky.
Home in Capannoli
4.88 out of 5 average rating, 32 reviews

Relax and style in Tuscany by the pool

Sally BeatriceRating, 5 stars70 months ago
After being scammed by a con artist who advertised a villa that was derelict we found ourselves with nowhere to go to celebrate my mother in laws 60th birthday. We had a Grandmother over 80 and two children under 3, nine people in total and absolutely no idea where to stay. After a desperate search on air bnb, we found this beautiful villa. Having auto-booked it, we crossed our fingers and hoped we wouldn’t be disappointed when we arrived the next day. I can safely say, we were not. The house is absolutely phenomenal. Beautiful, spotlessly clean and so stylish. It manages to be spacious and airy while retaining a coziness and Tuscan charm that we were originally looking for. Our host, was charming and accommodating. He gave us the privacy to enjoy his home while still being on hand for anything we might need. The bedrooms are beautiful and the beds were very comfortable with crisp linens and fans in each for those hot Italian nights. The swimming pool is enormous, perfect temperature and CLEAN thanks to both the man who came to clean it for us and the little robot that chugs around the bottom when we weren’t using it. The kitchen facilities are top notch and our gorgeous host left us a basket with ingredients to make fresh Italian pasta with basil for our first day. He also popped down with a bottle of champagne for the birthday celebration. So kind and thoughtful. The house is in a wonderful village with an exquisite little restaurant nearby that serves some of the best pasta I’ve ever had. Situated under an hour from Pisa, Florence and Lucca it’s ideal for day trips. We had an absolutely unforgettable time and if you come to Tuscany I can not recommend this property enough. Thank you to our beautiful host for making the week so perfect. Ciao!
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, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars7 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Guest favorite
A hammock is positioned among olive trees, providing a shaded spot overlooking a shared swimming pool. Comfortable lounge chairs are arranged around the pool area, with umbrellas offering additional shade. Lush, green grass completes the serene outdoor setting.
Home in Lucca
4.91 out of 5 average rating, 22 reviews

Casa Orfeo in estate with pool and beautiful view

EmmaRating, 5 stars9 months ago
The perfect place to stay in Tuscany, beautiful home and gardens. We loved the views and the amazing swimming pool. The house had loads of character and was very homely and comfortable. Loved the location, not too far from Lucca and only 30 mins from Pisa airport. Andrea was a very friendly and helpful host too. Wonderful stay - thank you!

Condo rentals with a pool

Superhost
A private swimming pool is surrounded by lounge chairs and umbrellas, inviting relaxation. A hammock offers a serene spot to unwind. Lush greenery frames the pool area, and the apartment structure is visible in the background, blending with the natural landscape.
Condo in Loro Ciuffenna
5 out of 5 average rating, 9 reviews

""Beautiful Villa with PRIVATE pool in Tuscany""

BahrinRating, 5 stars17 months ago
Nice scenary, quiet romantic Town, Nice small cafe beside the river. But what impress Me marco property I felt like Home right away. Secured electeric gate leaving Me no worries. Kids love it and kitchen are well equip!! Thanks marco for your beautiful place and hosting us!!! I recommend this place for quiet country side place.
Top guest favorite
A clear swimming pool set within a landscaped garden, surrounded by lush green trees and hedges. The pool features a light blue hue with sun glimmering on the water's surface, inviting relaxation. Sun loungers are positioned nearby for comfortable seating.
Condo in Soiana
4.98 out of 5 average rating, 48 reviews

Charming apartment with garden, pool and valley view

OskarRating, 5 stars3 weeks ago
Incredible accommodation that exceeded expectations, Francesco is a wonderful host who was very helpful and had local recommendations on everything. From best bakery to the winery not to be missed. Highly recommend and will probably come back!
Superhost
A two-level swimming pool is set amidst landscaped greenery, featuring a shallow area leading to deeper sections. Loungers are arranged in a sunbathing area surrounded by olive trees, while a rustic building is visible in the background, providing a scenic backdrop.
Condo in Pergine Valdarno
4.67 out of 5 average rating, 6 reviews

Relax in farmhouse among the Chianti vineyards

MeganRating, 5 stars9 months ago
Tuscan retreat = THIS. Set in a lovely, quiet area with gorgeous views of the landscape. Easy to get to Arezzo and only 1 hour from Florence. So many amazing local restaurants and Vineyards. The property itself has a traditional vibe to it. The kitchen is not well equipped, so just bare that in mind! minimal pots, pans etc. But otherwise looks exactly like the photos.
Superhost
A communal swimming pool is surrounded by lush greenery and tall pine trees. Sun loungers with blue cushions are positioned around the pool area, providing ample space for relaxation. A few umbrellas offer shade, and a well-maintained residence is visible in the background.
Condo in Rosignano Solvay-Castiglioncello
4.74 out of 5 average rating, 23 reviews

100mt from the sea - apt w/pool, wifi & tv

ShaneRating, 5 stars8 months ago
Brilliant host. Lovely apartment and nice area. Never bored.
Guest favorite
A serene outdoor pool with a stone border is surrounded by lush greenery, offering a peaceful view of the rolling hills in the distance. The bright blue water contrasts beautifully with the natural elements, providing a refreshing spot for relaxation.
Condo in Uzzano
4.83 out of 5 average rating, 23 reviews

Tuscan country apartment in a lovely olive grove

JudithRating, 5 stars1 week ago
Deborah was the nicest host! She welcomed us with kindness and prepared everything nice for our stay. We would totally recommend the stay there, when you are searching for a quiet stay, but want to go for some Citytrips as well. :)
Guest favorite
A tranquil swimming pool is illuminated by soft lighting, surrounded by lush greenery and olive trees. The night sky is filled with stars, creating a serene atmosphere, while a few lounge chairs are positioned nearby for relaxation.
Condo in Cortona
4.96 out of 5 average rating, 24 reviews

Relaxation and peace in the countryside Cortona G

Marie-HélèneRating, 5 stars9 months ago
We really enjoyed our stay! Emanuele and Angela were very kind and replied to any question very quickly. The place is perfect to relax and take day-trips to nearby towns such as Cortona, Pienza, Montalcino and Montepulciano. We enjoyed the pool after big days of visiting the surroundings during very hot days. I recommend it to anyone who wants a mix of visiting and relaxing! :)
Superhost
A shared swimming pool is set within a serene garden, surrounded by olive trees. Comfortable lounge chairs are arranged around the pool, complemented by a neat patio area. The clear water reflects the sunlight, enhancing the inviting atmosphere of the outdoor space.
Condo in Gavinana
5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

JeevanRating, 5 stars21 months ago
We had a lovely stay here - there were 8 of us in total across 4 spacious bedrooms and 3 bathrooms. It is a beautiful old villa with a big garden and a cute pool and barbecue area. It is possible to walk into the city of Florence (30 - 40 minute stroll) but we found a car was necessary to ensure that we could get around and eg buy groceries. There is a cash deposit required for check in, so it’s useful to withdraw that before you arrive. Our host was very responsive and helpful throughout our stay. Overall, we had a lovely time!
Superhost
A large swimming pool with a heart shape is set against a scenic hillside, offering views of the surrounding landscape. Lounge chairs with green umbrellas are neatly arranged along the poolside. Lush greenery frames the area, enhancing the tranquil setting.
Condo in Corsanico-Bargecchia
4.58 out of 5 average rating, 24 reviews

Frantoio di Corsanico - Lauro apartment

ChrisRating, 5 stars9 months ago
We stayed at the end of the season in this really nice area and felt right at home on site. The old oil mill and our apartment are generously allowed, corresponded to the description, the photos shown are even better in reality. It was all clean, all the equipment worked and we felt very comfortable. The large swimming pool is a real highlight and has greatly upgraded the stay, especially the children. The reception on site went smoothly and was very well prepared in advance. We enjoyed the time very much and can really highly recommend the accommodation - the value for money is great! Thank you Francesca, thank you Veronica, thank you Cristina and Sabrina!

Home rentals with a private pool

Guest favorite
A spacious living area features arched entryways and original wood ceilings. A cozy white sofa is positioned adjacent to a rustic wooden coffee table. Bright natural light pours in through multiple windows, illuminating the charming décor and the large stone fireplace adorned with seasonal flowers.
Home in San Casciano In Val di Pesa
4.84 out of 5 average rating, 92 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

JanetRating, 5 stars1 month ago
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!
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
4.98 out of 5 average rating, 191 reviews

Stone House with Exclusive Pool Codilungo in Chianti

ShoshiRating, 5 stars3 weeks ago
What a wonderful place! It’s hard to say whether the interior or exterior is more beautiful, both are absolutely stunning. The house is perfectly decorated and spotlessly clean. We enjoyed postcard-worthy views of Tuscany from the garden and loved the romantic design of the rooms. Our vacation was both fun and relaxing, thanks in large part to Giovanni, Emanuela’s son, who warmly welcomed us and assisted with everything we needed, including reserving a dinner table for us each night. Upon arrival, we were greeted with a thoughtful selection of treats such as milk, eggs, juice, beer, bread, local olive oil, Chianty Reserve wine, coffee, water etc. We even received homemade Italian cookies for Mother’s Day, a kind gesture from Giovanni that made us feel truly welcome. Usually, we stop at a market before check-in, but here we didn’t need a thing. They truly thought of everything. This place sets the bar high! Don’t miss dinner at Tricco, just a 3-minute drive away in the historic center.
Top guest favorite
Farm stay in Arezzo
4.97 out of 5 average rating, 227 reviews

Explore nature in the center of Vigneti Chianti

KathrynRating, 5 stars3 days ago
What a fantastic getaway! We loved stayed at Rita’s place and soaking up the peaceful Tuscan countryside. The interior space was so charming, and the exterior landscape was a dream. Rita made us feel right at home, and even had a bed and high chair prepared for our baby. She helped us decide where to eat and do wine tastings, and each recommendation was 10/10. Thank you Rita!
Top guest favorite
A decorative ceramic plate is mounted on a wall, featuring a colorful coat of arms. The design includes a shield adorned with stars and intricate detailing surrounded by floral patterns, providing a cultural touch to the interior space.
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars10 months ago
We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. There is plenty of parking. Only the potholes and the access to the villa are a bit challenging - but doable!
Guest favorite
An elegant stone cottage is surrounded by lush greenery, featuring multiple levels and outdoor steps leading to a private swimming pool. The structure showcases rustic architecture with clay tile roofs, large windows, and a tranquil setting in the countryside.
Home in Pescia
4.86 out of 5 average rating, 21 reviews

Aurora by Interhome

NatalieRating, 5 stars4 days 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 rustic wooden dining table is set with white plates and clear glasses, accompanied by ripe oranges and red tomatoes. In the center, a traditional clay jug is placed next to freshly baked bread. The surrounding stone wall and warm pendant light add to the inviting ambiance.
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 46 reviews

Charming villa in the Chianti hills

WilliamRating, 5 stars3 weeks ago
Idyllic. Beautiful place to recharge while being in easy reach of Florence and Sienna. After reading the previous review I was concerned it would be all that private. However, it was totally private. Francesca’s home is detached from the house and the outdoor areas (pool, dining and bbq) are screened by the buildings.
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 stars8 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, 95 reviews

Casa Luigi Suite with exclusive pool

RachelRating, 5 stars1 week ago
Our stay at Casa Luigi with Giovanna and Luigi was absolutely perfect. I wish I could give it more than 5 stars. Not only was the place absolutely spotless, even the grounds were perfectly attended to and such a pleasure to walk through and sit in. Giovanna and Luigi were both so kind and friendly - we felt right at home. The apartment itself was very comfortable and had everything our family of 4 needed. My two teenage daughters were thrilled to have their own sleeping spaces and greatly enjoyed just staying at the apartment to enjoy the space and the grounds on a few days. It was the first place on our trip all over Italy where we actually wanted to stay at the Airbnb instead of sightseeing! I wish we could have stayed longer. This place is an absolute gem and I cannot express how much we absolutely loved our stay there!

Quick stats about vacation rentals with a pool in Casole d'Elsa

  • Total rentals

    10 properties

  • Nightly prices starting at

    $60 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