A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

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Check availability on Castiglion Fiorentino Hotels with Pool

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Castiglion Fiorentino hotels with a pool

A hotel with a rooftop pool, a modern building with a sloped roof, and a view of the surrounding town.
A modern library with leather sofas, bookshelves, and a large window.
A hotel with a modern design, featuring a prominent green sign, multiple balconies, and well-maintained landscaping.
A modern bar area with a counter, bar stools, and a seating area with chairs.

1. Hotel Park

Hotel Park
Castiglion Fiorentino
  • Soak up the sun at this hotel's seasonal pool, surrounded by lounge chairs for ultimate relaxation.
฿3,550
฿4,056 total
includes taxes & fees
1 Nov - 2 Nov
Hotel Park
A pool area with lounge chairs, a hot tub, and a view of mountains.
A spacious room with a large window, a view of a landscape painting, and a desk with a vase of flowers.
A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.
A terrace with sun loungers, stone walls, and potted plants.

2. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
  • Luxurious indoor pool sanctuary awaits at this historic Cortona monastery, where relaxation flows from spa waters to garden views.
฿9,195
฿10,266 total
includes taxes & fees
8 Nov - 9 Nov
Monastero di Cortona Hotel & Spa
A person in a swimming pool with a view of trees and mountains through a window.
A spacious, well-lit restaurant with large windows, wooden tables, and potted plants.
A balcony with a table and chairs, a potted plant, and a view of a green landscape.
A stone building with a red awning, potted plants, and a staircase leading to the entrance.

3. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
  • Luxurious Tuscan retreat offers twin outdoor pools, winery access, and poolside dining with stunning vineyard views.
฿12,406
฿13,798 total
includes taxes & fees
15 Nov - 16 Nov
Il Falconiere - Relais e Chateaux
A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.
An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.
A hotel lobby with a brick archway, a reception desk, and potted plants.
A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.

4. Hotel Le Capanne

Hotel Le Capanne
Arezzo
  • Splash into seasonal bliss at this 24-hour rural pool escape with mountain views and refreshing freedom.
฿3,560
฿4,143 total
includes taxes & fees
2 Nov - 3 Nov
Hotel Le Capanne
A landscaped garden with a swimming pool, neatly trimmed hedges, and outdoor seating areas.
A long dining table set with plates, glasses, and floral centerpieces, surrounded by chairs.
A restaurant with glass walls, tables set with white tablecloths, and chairs.
A building with arched windows and a well-maintained garden with trimmed bushes and a large flower pot.

5. La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
  • Discover a Tuscan escape with a vineyard-view pool, winery tours, and farm-to-table dining.
฿3,331
฿3,891 total
includes taxes & fees
2 Nov - 3 Nov
La Cantina Relais - Fattoria Il Cipresso
Pool
Breakfast buffet
Outdoor spa tub
Exterior

6. iConic Wellness Resort

iConic Wellness Resort
Arezzo
฿2,509
฿2,987 total
includes taxes & fees
16 Nov - 17 Nov
iConic Wellness Resort
A swimming pool with a green-lit edge, a glass-enclosed structure in the background, and a bench near the pool.
A bathroom with a stone wall, a large bathtub, and a glass-enclosed shower area.
A bedroom with a bed, a chair, a table with a candle, and a wardrobe.
A spacious hallway with wooden flooring, a wooden cabinet with a mirror, and two candle lanterns.

7. Cortona Resort Spa

Cortona Resort Spa
Cortona
  • Serene seasonal outdoor pool awaits at this rural Italian resort, where massages and hiking trails beckon.
฿5,401
฿5,997 total
includes taxes & fees
15 Nov - 16 Nov
Cortona Resort Spa
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
An outdoor dining area with tables set for a meal, surrounded by greenery and trees.
A large estate with a swimming pool, surrounded by lush greenery and hills.
A hallway with a checkered floor, arched windows, and a chandelier.

8. Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World
Cortona
  • Tuscan escape with poolside lounging beneath cypress trees and vineyard views.
฿22,940
฿25,536 total
includes taxes & fees
24 Oct - 25 Oct
Villa di Piazzano - Small Luxury Hotel of the World
A swimming pool with lounge chairs and umbrellas, a building with a sign reading "OLOS", and a clear blue sky.
A modern hotel with a glass facade, a lounge area with seating, and a staircase leading to an upper level.
A modern hotel room with a unique geometric design, a large bed, a desk with a computer, and a circular seating area.
A hotel corridor with a carpeted floor, a bed, and a door with curtains.

9. A Point Arezzo Park Hotel

A Point Arezzo Park Hotel
Arezzo
  • Serene outdoor pool escape with poolside cocktail bar and loungers creates the perfect Italian countryside retreat.
฿2,721
฿3,220 total
includes taxes & fees
25 Oct - 26 Oct
A Point Arezzo Park Hotel
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A bedside table with a vase of flowers, a book, and a drawer.
A person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.
A person in a white robe standing by a window with a view of mountains.

10. Locanda agli Amici

Locanda agli Amici
Cortona
  • Discover seasonal poolside bliss with rooftop views, sun loungers, and umbrellas at this upscale family-friendly retreat.
฿3,404
฿3,896 total
includes taxes & fees
2 Nov - 3 Nov
Locanda agli Amici
View all properties

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

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Castiglion Fiorentino Hotel Reviews

Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Nice hotel in a great location, very close to Pienza’s historic center. The room was clean, and the staff were helpful. Breakfast could be improved, particularly in terms of the variety of hot food available. The daily parking fee was also somewhat expensive."
Ramon 4-night trip
Posted 2 days ago
Hotel San Gregorio
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Absolutely beautiful! Astonishing views! If you are looking for peace and quiet with great service this is the place."
Maribel 2-night trip
Posted 2 days ago
Relais Villa Grazianella - UNA Esperienze
Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"It's a lovely hotel, but it is the staff that make it truly special. Attentive and cheerful, I felt well looked after from the moment I walked in. Wonderful stay, I'll definitely be back."
Doralba 2-night trip
Posted 5 days ago
Hotel Villa Ricci
Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

8/10 Good
"Ok."
Yuanjun 1-night trip
Posted 2 weeks ago
Hotel Panoramic Montepulciano

Frequently asked questions

What's it like visiting Castiglion Fiorentino?
If lounging next to a pool is your idea of the perfect getaway, you might want to think about historic Castiglion Fiorentino, which has 11 places to stay with pools. While you're here, you can explore sights such as Val di Chiana and Tennis Club Castiglionese, and then kick back and relax poolside at one of the accommodation options in Castiglion Fiorentino that guests like for their pools.
What are some accommodation options with pools in Castiglion Fiorentino?
Villa di Piazzano - Small Luxury Hotel of the World: Features a snack bar/deli, an outdoor pool and free self parking. Nuovo Etruria Resort: Offers televisions, a seasonal outdoor pool and complimentary bottled water. Precise Tale Poggio Alla Sala: Provides a seasonal outdoor pool, an indoor pool and a full-service spa. Hotel Continentale: Offers a full-service spa, an indoor pool and a sauna. Monastero di Cortona Hotel & Spa: Features sunloungers, an infinity pool and complimentary wireless Internet access.
How many pool hotels will I find in Castiglion Fiorentino?
Expedia has 11 hotels in Castiglion Fiorentino for your poolside break.
What is there to see and do in Castiglion Fiorentino?
Surround yourself with nature at Val di Chiana. During your stay, visit sights such as Tennis Club Castiglionese, Vasari Loggia and Archaeological Museum.
When is the best time to book a hotel with a pool in Castiglion Fiorentino?
You may want to consider a place to stay with an outdoor swimming pool if you're planning to visit Castiglion Fiorentino in the hottest months of August, July or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is 6°C.
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. If you want to venture outside the area, hop on a train at Castiglion Fiorentino Station. Castiglion Fiorentino may not have many public transport options to choose from, so consider a car rental to maximise your time.

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