Hotels in Chianti with a Pool

We travelled as a group of four persons and this Agriturismo was our favourite place throughout our whole Italy round trip.

My family of 3 adults stayed at Due Piani for 5 nights at the end of December 2023 into early January 2024 and we wish we could have stayed longer!

If I had to describe this place with one word, i'd say "heavenly". My stay in Santa Maria a Poneta was short yet unforgettably beautiful.

This place was my favourite the weather was great and the workers were very nice the location was great with a supermarket nearby and lots of restaurants as well with great locations all around.

Great stay, clean rooms, delicious food (especially the truffle dishes) and great service, thanks to Bartolomeo the best waiter in the world and to Helen.

Thank you for a wonderful visit!

Last minute check in to this very central hotel. Super friendly receptionist. Slightly faded common parts. Room was comfortable but was the last available so wasn’t their best!

A charming hotel with an amazing gracious staff. Loved the room for my six day stay with the ambiance of the vintage appeal.

We spent two unforgettable days at this beautiful agriturismo in Chianti with a group of 24 people, and it was absolutely perfect.

Came here for my best friend’s wedding — we spent a week at the venue and all I can say is it is a must-stay. Beautiful, romantic, spacious and perfect for large groups. Could not recommend enough!

Came here with the family for dinner, everything we got was delicious from the T bone steak to the risotto. The staff were incredibly helpful and nice.

10/10! We had a fabulous stay at Fattoria di Corsignano. The staff were very lovely, spacious room, peaceful property with amazing views and delicious restaurant and wine!

Our family of 4 including 2 teenagers loved our peaceful stay. Giuliana and the rest of the team were very warm and welcoming. The view was beautiful.

Hidden secret that is a must visit in this area! ☀️🤌🏻🍷🍇
We had a spontaneous wine tasting and a private tour with Chiara, how made the whole experience super special.

A very beautiful and peaceful place with amazing views.
The room is very clean, and the host is very kind and friendly.
There is a nice swimming pool and a BBQ area to enjoy.

The villa is beautiful and well kept. Super clean with a deck, tables outside to eat and a pool. It’s in my the middle of Tuscan countryside. Highly recommend!

This is a lovely property at a reasonable price. The pool was clean and well maintained. The rooms were comfortable and bathrooms were very modern. We enjoyed a very nice meal in the restaurant.

What a little gem! We were on a tour exploring Tuscany and found this treasure late at night when looking for a place to settle down for a few days.

Very good location but hard to access without a car in the evening.

We had a nice stay. The house is lovely and has a very authentic Italian feel to it. Clean and has lots of useful amenities. It was possible to get a taxi into the city from there easily.

The second time we’re here with our little one (7months old baby). Everybody is happy. So great and clean space. We rented the first time deluxe bungalow which is fantastic, new and clean.

Excellent rooms felt like first class. The location and the features that are included and available are amazing.

Stayed in October 2017, after reading, On the Rocks and Catching Fireflies by Tony Rocca, driving force in bringing this property back to life. Such fond memories. Stayed in the "Owl" suite.

Such a perfect place to stay on a vineyard. Staff were very friendly and accommodating. Sunsets were beautiful over the hills.
And the cute towns around it were so close which was nice.

We had the most beautiful wedding at Borgo Petrognano this past October, and it truly exceeded every expectation. The venue itself is absolutely breathtaking! Pictures don’t even do it justice!

Wow—where do we even begin…
We chose Borgo Petrognano for our 30-person destination wedding in Tuscany in September 2025, and it was truly perfect.

We rented the villa for a week and it was wonderful. It really felt like we were living in this beautiful area ourselves. We'd never had such a spacious terrace with such a stunning view.

Time has taught me that hard earned holiday opportunities are precious, so much changing world to see in so little time that it rarely makes sense to 'go back'… and yet I find myself here yet again

Villa Talciona is just stunning. The views, location, quietness make you feel like in total peace. Francesco and Elena welcome you with open arms. Their own food was really good. Highly recommended.

This is a very chill and cool place. You can rent the apartment downstairs. Francesco and Elena are the nicest people 👍🏻

Gorgeous pool, views and grounds. Alessandro is so kind and helpful. Our accommodation was spotless and spacious.

What a nice week we had!
The owner is very nice. He was always there when you needed him. The guided tour at the beginning was also excellent.
What a beautiful environment.

Great location, even greater host. Thank you Stefano for a wonderful time! We highly recommend this fattoria! The view is breathtaking. Our apartment was comfortable and had everthing we needed.

A beautiful setting with lovely views, quiet and totally relaxing.

Great location, excellent hosts, perfect place for excursions around Tuscany, especially Chianti region.

The most incredible peaceful relaxing and beautiful place, we couldn’t fault it. Accommodation was spotless. Anastasia is so helpful and gives recommendations for your week if you need any.

Our AC wasn’t as fantastic as our other friend’s rooms. The castle is super charming though, and the views are insane.
Pool is great too. And breakfast was fantastic.

Awesome place. Everything was top notch. Rooms were great. Grounds are beautiful. Staff is friendly & super accommodating. Will stay again & recommend fully.

Lovely space, lovely pool area. Room of high quality.
Friendly staff. Relaxing place to stay.
Breakfast was very good.
Evening meal was disappointing.

Our family of 15, ranging from 8 months to over 70 years old, stayed at this magical little hotel in Tuscany, and every single one of us had an incredible time.

I can say I like this!

We spent three days in this farmhouse.
Clean environment and very large and spacious rooms.
Alessandra, the owner, is very nice and thoughtful. We tasted his cuisine, highly recommended.

Aia Country Holidays,
✨ Just wrapped up a charming stay — the place was super clean, simple, and had everything reduced to what you actually need. Sometimes less really is more.

Spacious, clean room in a very calm neighborhood, 5 minutes drive to get to the parking in front of center of Siena. Really good, personalized breakfast.