
Vacation rentals with a pool in Gaiole in Chianti
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Top-rated rentals with a pool in Gaiole in Chianti
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Popular amenities for Gaiole in Chianti rentals with a pool
House rentals with a pool

Casa Fattore - Tuscan countryside house
The stay at the Capocontro estate was very satisfactory. The entire old village is a jewel set in the greenery, with spectacular views of the woods of the Val di Chiana. The place is tidy and clean, picturesque and elegantly retro. Piero and Lella are very available in communications and suggestions of places to visit and eat. We loved the peace and quiet of the place, as well as the pool with a view. We stopped little and the weather was a little capricious, otherwise we would have enjoyed the exteriors of the farm more. Only small mole: the dishes and the fridge were not really immaculate, but nothing that can't be resolved with a sponge shot. Highly recommended for both a short and long stay, so you can enjoy the quiet of the place and visit the surroundings.

La Limonaia della Torretta
Perfect stay in Leonardo's beautiful house. I highly recommend it to all travelers in Florence. The house is beautiful and the garden and the pool are extraordinary. Leonardo is extremely attentive and very kind. To be recommended absolutely.

Villa in Tuscany - Reggello, with pool and WiFi.
Beautiful tranquil villa set in picturesque grounds full of homegrown produce; a true taste of Tuscany. Pool is a perfect size and depth for a workout or just to relax and keep cool. Really useful to have the outside bbq area which we used a lot. Conveniently situated just outside the small town of Reggello with plenty of restaurants to choose from and a good size supermarket that has everything you need. Hosts really friendly and helpful but not intrusive. Felt like a home from home. Highly recommend.

Countryside house with private pool and garden
Such an amazing place! I would recommend EVERYONE to go there! Violante and her husband are such nice hosts. We had a wonderful time there and will not hesitate to come back next year. Thanks a lot.

Little Poventa
casale polenta exceeded our expectations. beautiful property and accommodations.

CHARMING TUSCANY VILLA PRIVATE POOL
Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.

"Casa Elisa", house with pool at the foot of Cortona
I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.

Converted barn in Tuscan olive grove
This has been by far one of the most perfect holiday villas we’ve rented! Nestled in the most peaceful of locations, the villa was absolutely charming! Waking up to the sounds of birds chirping was a definite mood booster! We were relieved to see that there were herbs, oils and cooking condiments ready to use. The pool was a huge bonus and we used it most days. Seeing as we went in August, the outdoor temperature was very very hot, but luckily the house remained cool with its air con system. For anyone who wants to escape the hustle and bustle and doesn’t mind hillside driving, we highly recommend it! I would just mention that a few more hooks in the bedrooms to hang things on would be beneficial but didn’t impact our enjoyment whatsoever! Thank you to Charly for excellent check in and check out instructions. Big hugs from the UK!
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.

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.

ideal for two + loggia, pool on the farm
We had a great stay in this beautiful place. The farmhouse has several apartments each with their privacy. The pool was very clean and hot, there was shade available and a shower and toilet right next door. The apartment was as in the photos, there was no air conditioning but it was very cool inside during the day. A few days before our arrival, Isabella sent us all the necessary information and it was her brother Piero who welcomed us very warmly when we arrived. The place was very clean, the kitchen well equipped and bath linens were provided. There are many things to do and see in the area, we even had recommendations available. Overall we are really happy and would definitely recommend this place!

Three-room apartment with 2 bedrooms and private garden, pool
Wonderful place, very nice host. Thank you for your hospitality, Silvia

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!

lovely farm- apartment (Fox)
My fiance and I loved our stay here. beautiful views and prestige grounds. there were also a few friendly cats which made my fiancé's day. You need a car when staying here. you can find good restaurants and a grocery store a few minutes away in San casciano. It's centrally located in tuscany. 30 minutes to florence, 45 mins to siena. With lots of historic towns and wineries close by. The apartment was well accommodated, clean, and we'll equipped for cooking. We did pick up a few extra necessities from the grocery store and found the shower a little small, but otherwise found the stay comfortable and relaxing. Would totally recommend to friends and come back.

Panoramic apartment with pool and private garden
The photos don’t do this place justice! I encourage anyone to book it, we absolutely loved it. The views are gorgeous, and the apartment is really big. We particularly loved the location, it’s very central to all the major spots. Stefano was so helpful, and kind.. thank you!!

PodereCupiano "Le Fornaci"
Francesco was very welcoming and in addition, the site is beautiful and very well maintained. The pool with mountain views is really great! A beautiful place to relax in peace. The road to get there is a little long and very tortuous, but this is often the case in Tuscany...
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
The Stone House was gorgeous - beautifully and thoughtfully decorated, with amazing views. It was private yet easy to get to many amenities/tuscany towns/wineries nearby. Emanuela and Giovanni were very responsive to our questions and requests. We requested for help to buy a bouquet of flowers to surprise our friend for her birthday on the day we arrive - not only did they take the time to help us buy it, they refused to let us pay for it! it was too cold for us to use the pool but I can imagine how wonderful it would have been if we could have used it. all in all, it was a great place to enjoy a dreamy tuscan holiday.

Casale il Poggio by Interhome
We had a very good time here! The Airbnb is a separate part of a nice house on a hill, it is spacious and has everything you need. You can sit outside and there is a nice swimming pool. The hosts were very nice and always available for help/tips. I definitely recommend this place!

Explore nature in the center of Vigneti Chianti
A big thank you Rita and Sonali!

Villa 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. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!

Charming villa in the Chianti hills
We spent some nice autumn days at Francesca's place. It's much nicer than it's pictured. The house is fantastically and quietly located on a hill. The amenities are high quality and Francesca was always available at short notice. We would definitely go on vacation there again.

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!!

Suite Casa Luigi with exclusive pool
Giovanna was such a wonderful host. It felt like a home away from home, with special touches added such as some food and wine in the apartment on arrival, and even a farewell drink before we left. The cottage is in breathtaking surroundings and in a perfect location to get around and explore different parts of Tuscany (with a car). I would highly recommend to anyone visiting the area ! We hope we can go back again one day!! Thank you Giovanna and Luigi !!

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool
We had a fantastic stay with a group of four adults and five kids. Accommodations were immaculate, private chefs were decadent and delicious, and fantastic wine. The grounds were just lovely as well and we enjoyed having a fire in the fire place every evening. That you for a lovely stay!
Quick stats about vacation rentals with a pool in Gaiole in Chianti
Total rentals
10 properties
Nightly prices starting at
$87 CAD before taxes and fees
Total number of reviews
150 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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