The Best Hotels with a Pool in Castiglion Fiorentino from ₩131,731 in 2026

Q: What are some accommodations with pools in Castiglion Fiorentino?

Villa di Piazzano - Small Luxury Hotel of the World : Features kitchens, a pool, and televisions. Monastero di Cortona Hotel & Spa : Offers a snack bar/deli, an outdoor pool, and free self parking. Precise Tale Poggio Alla Sala : Provides a full-service spa, an indoor pool, and a sauna. Nuovo Etruria Resort : Features a seasonal outdoor pool, an indoor pool, and a full-service spa. Hotel Corsignano : Offers televisions, a seasonal outdoor pool, and complimentary bottled water.

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Our top choices for Castiglion Fiorentino hotels with a pool

Borgo Sant'Ambrogio Resort

Trequanda

Splashy seasonal pool moments at this lakeside farm stay with Italian restaurant and garden oasis.

₩279,613 total

includes taxes & fees

Jul 1 - Jul 2

Indoor pool, open 9:00 AM to midnight, sun loungers

Albergo San Biagio

Montepulciano

Elegant indoor pool sanctuary with a dedicated kids' pool creates splashy vacation magic for all ages.

₩131,731 total

includes taxes & fees

Jun 7 - Jun 8

La Torre ai Mari

Sarteano

Escape to a seasonal mountain oasis where sun-drenched pool loungers and shady umbrellas create the perfect summer retreat.

₩199,964 total

includes taxes & fees

Jun 3 - Jun 4

Villa Schiatti

Castiglion Fiorentino

₩288,018 total

includes taxes & fees

Jun 11 - Jun 12

Hotel Park

Castiglion Fiorentino

Soak up the sun at this hotel's seasonal pool, surrounded by lounge chairs for ultimate relaxation.

₩188,563 total

includes taxes & fees

Jun 1 - Jun 2

Residenza Dei Ricci Relais

Chiusi

₩285,474 total

includes taxes & fees

Jun 1 - Jun 2

Seasonal outdoor pool, a rooftop pool, pool umbrellas, sun loungers

Locanda Vesuna

Trequanda

₩262,585 total

includes taxes & fees

Jun 2 - Jun 3

Cortona Resort - Le Terre Dei Cavalieri

Cortona

Elegant farmhouse pool retreat immerses guests in the Tuscan countryside with dining steps away.

₩230,640 total

includes taxes & fees

Jun 4 - Jun 5

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Choose what matters most at hotels with a pool in Castiglion Fiorentino

Breakfast included

4 stars

Top Castiglion Fiorentino Hotel Reviews

Agriturismo La Sovana

10/10 Excellent

"I have nothing but rave reviews for this resort!! I came with my 2 sisters for a special birthday trip and the second we arrived there our jaws were on the ground when we saw how beautiful this place was. Seriously the pictures online don’t do it justice! When we arrived Fiorella greeted us and immediately treated us like family. She made sure every aspect of our stay went smoothly. We felt bad because we were new to Italy and had a million questions everyday but she was truly our little fairy godmother helping us navigate our days! She helped us plan and coordinate our visits in the Tuscan countryside and even booked wine tastings for us since we didn’t know what we were doing. She is fantastic with planning and just being available to help and was just such a joy to talk to! We didn’t rent a car which in hindsight I almost wish we did because getting around isn’t the easiest since there are not a ton of taxis in the country side but the owner of the resort Guiseppe was so kind and helped get us to our destinations a few times which he did out of the kindness of his heart! The other staff members also called and arranged taxis when available for us! They truly treat you like a part of their family here. We did a wine tasting of their homemade wine and it was all so delicious! We all ended up ordering wine and olive oil to be shipped home so we can enjoy it when we miss Italy! Honestly, every staff member was beyond wonderful and we couldn’t have picked a better place! 10/10!"

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 Castiglion Fiorentino?

If spending time by the pool is your idea of the perfect getaway, you may want to check out historic Castiglion Fiorentino, which has 17 places to stay with pools. While you're here, you can explore sights such as Val di Chiana and Cassero Tower, and then relax and unwind poolside at one of the accommodations in Castiglion Fiorentino that guests like for their pools.

What are some accommodations with pools in Castiglion Fiorentino?

Villa di Piazzano - Small Luxury Hotel of the World: Features kitchens, a pool, and televisions. Monastero di Cortona Hotel & Spa: Offers a snack bar/deli, an outdoor pool, and free self parking. Precise Tale Poggio Alla Sala: Provides a full-service spa, an indoor pool, and a sauna. Nuovo Etruria Resort: Features a seasonal outdoor pool, an indoor pool, and a full-service spa. Hotel Corsignano: Offers televisions, a seasonal outdoor pool, and complimentary bottled water.

How many pool hotels can I expect to find in Castiglion Fiorentino?

Expedia's 17 hotels in Castiglion Fiorentino give you a great choice for your poolside getaway.

What is there to see and do in Castiglion Fiorentino?

Surround yourself with nature at Val di Chiana. During your stay, check out sights such as Cassero Tower, Tennis Club Castiglionese, and Agricola Buccelletti Winery.

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

You may want to consider a place to stay that has an outdoor pool if you're planning to visit Castiglion Fiorentino in the hottest months of August, July, or June when the average temperature is 71°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 temperature is 42°F.

What's the best way to travel around Castiglion Fiorentino?

Knowing the transportation options in and around Castiglion Fiorentino can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, ride aboard one of the trains from Castiglion Fiorentino Station. Castiglion Fiorentino might not have many public transportation choices so consider a car rental to maximize your time.

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