Vacation rentals with a pool in Casole d'Elsa

Breathtaking location with views that are exactly what you want in the Chianti region. It was a beautiful place and was very nicely setup. Extremely responsive and helpful host. He provided recommendations and was quick to respond to questions. The house is centered nicely within the region and allows access to many different villages, wineries, and restaurants. An amazing experience and I highly recommend!

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!

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!

Amazing location and responsive host. Incredible pool with an outstanding view. House, especially the Kitchen, was well well stocked with amenities needed. Highly recommended!

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 got good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he was able to move freely. We would come back back. It was an incredibly beautiful time!

We loved stating here. Norma and her family are all incredibly nice. We didn’t get to use the pool much because of the weather, but overall we had a great time. Perfect for relaxing.

We thoroughly enjoyed our stay at this wonderful place. The quiet surroundings were perfect for a break from the hustle and bustle of Florence. And it's still easily accessible by tram. Giacomo was a wonderful host and was always available. We truly enjoyed every day there.

Il Paluffo was a beautiful place in the Tuscan hills. Stilla, our accommodation, was relaxing and provided most everything we needed. The views were amazing and the staff friendly. The highlight of our stay was the cooking class with Monica. She was a burst of energy and patient as she guided us through a 4-course meal. It was absolutely delicious and plentiful. I would stay a Il Paluffo again and recommend to anyone.

We had a great stay in Francesca's agriturismo. beautiful place with breath taking views. the place was very clean and tidy and it had all we needed and much more. it was a good base for traveling the area. take a ride on the SP146 - you won't regret it! all in all this place is highly recommended! wish i would visit here again. Toscany is soo beautiful.

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.

Great place to stay for the small town Italian vibe. My wife and I stayed here for a few days as part of our honeymoon and we were welcomed and helped in very well. Benedetta help set us up with a cooking class which was a great time and some horse back riding the next day. Great place!

We had a wonderful time at Anna’s villa. The place is beautifully located within an easy walk to the tram station. The villa is absolutely stunning and full of history which Anna was more than happy to talk about. Anna is a wonderful host, always ready to share tips and recommendations. She made us feel right at home. We wouldn’t hesitate to come back at any time! :)

My husband and I adored the tranquility of this stay. Our host Oscar was so proactive, responsive, and helpful. We are so grateful for the kind acts of service Oscar and his team extended towards us. I have Celiac and they took into serious consideration ways to prevent cross contamination and made sure that there were options available for me. Their restaurant was likely the best food that we’ve tasted throughout our stay in Italy! The lobby is filled with its aroma of fresh herbs being cooked. We also adored the little furry friends that would hand around our porch! He had a team of people who would take us to and from the nearest train station and were extremely flexible! The stay is up a mountain so we were so thankful there was someone skilled enough to drive us up and down! Oscar, thank you for everything! We definitely plan to visit again and strongly recommend that anyone stay at your accommodation for peace, tranquility, and amazing food!

This place is such a gem! The hosts work hard to make sure your stay is very comfortable. Someone is at reception most of the time to answer questions or help with recommendations! The room we stayed in (Olivo) was perfect. It had a small kitchen with beautiful views and the nature of the building is "Tuscany Picture Perfect" You definitely need a vehicle to Get around unless you plan on taking a taxi and staying at the location (which is very doable since they have a restaurant and serve you breakfast every morning) The pool is beautiful with picture perfect hills of Tuscany while you swim! They have a small playground and a large yard with tables where you can sip wine or have a picnic! The bed was very comfortable and our stay here was very relaxing! The restaurant had such an amazing food as well! 10/10 would recommend!

Wonderfully spacious apartment with swimming pool in a beautiful authentic village with nice restaurants, in the middle of Tuscany. Around the corner, you can find fantastic mountain bike trails and hiking trails. Siena and Florence are also almost around the corner. We have enjoyed it!

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!

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!

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.

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!

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!

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

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.

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!!

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!