
Vacation rentals with a pool in Casole d'Elsa
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Top-rated rentals with a pool in Casole d'Elsa
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Popular amenities for Casole d'Elsa rentals with a pool
House rentals with a pool

The Limonaia della Torretta
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.

Tuscan Villa with Privacy,Pool,near towncentre
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!!

Country Cottage with Pool "Il Melograno"
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

Deal 2019 Tuscany Villa le Capanne with pool
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.

Pisa / Lucca-Superb Location-Leaning Tower views!
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.

Relax and style in Tuscany by the pool
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!

Casa di Lyndall - Entire house with exclusive pool
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!

Casa Orfeo in estate with pool and beautiful view
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

""Beautiful Villa with PRIVATE pool in Tuscany""
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.

Charming apartment with garden, pool and valley view
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!

Relax in farmhouse among the Chianti vineyards
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.

100mt from the sea - apt w/pool, wifi & tv
Brilliant host. Lovely apartment and nice area. Never bored.

Tuscan country apartment in a lovely olive grove
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. :)

Relaxation and peace in the countryside Cortona G
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! :)

Luxury Views aircon Shared Pool parking cooking
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!

Frantoio di Corsanico - Lauro apartment
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

Tuscan Villa Featured Conde Nast Best Villas Italy
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!

Stone House with Exclusive Pool Codilungo in Chianti
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.

Explore nature in the center of Vigneti Chianti
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!

Historic home with exclusive pool
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!

Aurora by Interhome
We had a lovely week at this place. In particular, the outdoor area was fantastic! Thank you and happy to come back!

Charming villa in the Chianti hills
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.

Villa il Palagio in the Tuscan countryside
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!!

Casa Luigi Suite with exclusive pool
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
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Gulf of Baratti
- Basilica of Santa Maria Novella
- Mugello Circuit
- Fortezza da Basso
- Parco delle Cascine
- Cala Violina
- Uffizi Gallery
- Piazzale Michelangelo
- Kite Beach Fiumara
- Piazza della Repubblica
- Mercato Centrale
- Marina di Grosseto beach
- Spiaggia Verruca
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Medici Chapels
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Spiaggia Libera
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