The Best Hotels with a Pool in Asciano from ₩124,620 in 2026 | Expedia

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Check availability on Asciano Hotels with a Pool

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Jun 12 - Jun 14

Our top choices for Asciano hotels with a pool

Outdoor pool, a rooftop pool, sun loungers

Castello di Leonina Relais

Asciano

Luxurious medieval castle with rooftop and natural pools offers serene countryside swims and poolside dining.

₩277,538 total

includes taxes & fees

Jun 21 - Jun 22

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Precise House Montaperti Siena

Asciano

Float in warmth year-round at this Italian retreat, where two pools complement soothing spa treatments in the Siena countryside.

₩241,516 total

includes taxes & fees

Jun 7 - Jun 8

Seasonal outdoor pool

Hotel Borgo Casabianca

Asciano

₩425,467 total

includes taxes & fees

Jun 9 - Jun 10

Seasonal outdoor pool

Albergo Diffuso Borgo Santo

Asciano

₩396,478 total

includes taxes & fees

Jun 8 - Jun 9

Seasonal outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas

Agriturismo San Sano

Gaiole in Chianti

Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.

₩226,295 total

includes taxes & fees

Jun 10 - Jun 11

Seasonal outdoor pool, open 9:30 AM to 7:00 PM, pool umbrellas

SI Montalcino Hotel

Montalcino

Sparkling tuscan poolside retreat offers a refreshing escape with scenic vineyard views.

₩238,158 total

includes taxes & fees

Jun 17 - Jun 18

Exterior

Relais la Costa - Dimora Storica

Monteriggioni

Tuscan splendor meets poolside relaxation at this luxury property with seasonal rooftop swimming and spa services.

₩357,721 total

includes taxes & fees

Jun 9 - Jun 10

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Choose what matters most at hotels with a pool in Asciano

Breakfast included

4 stars

Top Asciano Hotel Reviews

Castello di Leonina Relais

Castello di Leonina Relais

10/10 Excellent

"Really enjoyed our stay, clean room and property. Very quiet place with a nice pool."

Hotel Italia

Hotel Italia

10/10 Excellent

"Great place if you want to stay right outside the ZTL zone and the wall (beware of that if you are driving). Such a gem of hotel. The staff was super helpful, very kind and serviceable, i mean really really really nice. The room was a little tight for 4, but the bathroom was huge! All super clean, really impeccable. Our bedroom was in the adjacent building but in the ground floor, which made rolling in the luggage a breeze. The room itself had a queen bed and a day bed with a trundle. They were so nice and had the beds made for 4 when we arrived, i.e. they took out the trundle and made the bed as well as the daybed. I yet have to see that happen in the US... very attentive to detail. A very very minor thing, but the bed covers should be updated to be a bit more modern, looked like my grandma's curtains. Nevertheless, it was perfect for one night and also greatly appreciated the AC. The brick ceilings were also very charming. The breakfast buffet is absolutely amazing! Well worth the stay. They also have parking, but you need to reserve it ahead. We had gotten an email a couple of days before, but bc we were traveling around, I missed their ask if we wanted parking. Nevertheless, we found parking right behind the building so didn't matter at all, but you need to ask ahead for parking as they have limited spots A walk to the center if town is about 20mn and very easy stroll. This place is just perfect!! And Siena is just one of my favorite cities in Italy!!! Perfect combo!"

Dievole Wine Resort

Dievole Wine Resort

8/10 Good

"While everything was wonderful it was shame that our shower water was leaking out to the bathroom floor. Had to use extra towers to soak up the water. If we were staying more than a night, I would have ask to change the room. Other than that, staffs were wonderful, the dinner was delicious and the olive oil tasting experience was fun. Would highly recommend least two nights stay here. We wanted to extend our one night stay but the weather called for rain next day."

Borgo San Felice Resort

Borgo San Felice Resort

10/10 Excellent

"Wow wow wow. What a place. Absolutely phenomenal stay here. The grounds and hotel are absolutely fabulous. I read some review around staff attitude but can honestly say I never experienced this at all. Everyone was very polite and helpful in the bar and restaurants. George on reception was particularly lovely and helpful. The food and drinks were beautiful. I also did the wine tasting during my stay which was also wonderful. I will definitely be back."

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"I cant think of a more perfect place to stay. It is a beautiful property, with a long history, in one of the most beautiful regions of the world. We had one of the more "basic" rooms but it was still luxurious and comfortable. Amenities were great and the food/wine was amazing. We had some logistical problems with some of our travel plans and the staff was incredibly helpful. We are very grateful to Andrei, Kristian and Valeria especially. "

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"The Hotel and grounds are beautiful and immaculately maintained. The entire staff really stands out. So friendly and welcoming. Those little gestures of respect and kindness are appreciated. Also it’s very convenient that they can speak English. There are several beautiful hotels in the area to experience, however I would choose to come back here.."

Frequently asked questions

What's it like visiting Asciano?

If relaxing by the pool is your idea of the perfect getaway, you may want to check out relaxing Asciano, which has 14 places to stay with pools. During your visit, you can explore sights such as Monte Oliveto Maggiore Abbey and Val di Chiana, and then unwind poolside at one of the accommodations in Asciano that guests like for their pools.

What are some accommodations with pools in Asciano?

Castello di Leonina Relais: Features a sauna, a rooftop pool, and spa services. Precise House Montaperti Siena: Offers a seasonal outdoor pool, an indoor pool, and a full-service spa.

How many pool hotels can I expect to find in Asciano?

Expedia has 14 hotels in Asciano for your poolside break.

What is there to see and do in Asciano?

The picturesque setting of Val di Chiana showcases the area's natural beauty. Discover sights such as Monte Oliveto Maggiore Abbey and Museo Cassioli during your stay. Take in the natural beauty of Asciano with the countryside.

When is the best time to book a hotel with a pool in Asciano?

You may want to consider a place to stay that has an outdoor pool if you're planning to visit Asciano in the hottest months of August, July, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 44°F.

What's the best way to travel around Asciano?

Knowing the transportation options in and around Asciano can help you enjoy the area beyond your hotel pool. If you want to see more of the area, hop aboard a train from Asciano Monte Oliveto Maggiore Station, Asciano Station, or Castelnuovo Berardenga Station. Asciano might not have many public transit options so consider a car rental to maximize your time.

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