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

Hotels with Swimming Pool in Castiglion Fiorentino, Tuscany

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Castiglion Fiorentino Hotels with Swimming Pool

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 hotel lobby with a reception desk, seating area, and a large plant.

1. Hotel Park

Hotel Park
Castiglion Fiorentino
  • Soak up the sun at this hotel's seasonal pool, surrounded by lounge chairs for ultimate relaxation.
P6,649
P7,597 total
includes taxes & fees
Oct 20 - Oct 21
Hotel Park
A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.
A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.
A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.
A rustic outdoor dining area with stone walls, a table, and wicker chairs.

2. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
  • Dive into cooling bliss at this upscale hotel's seasonal outdoor pool with lounger service and refreshing drinks.
P7,390
P8,694 total
includes taxes & fees
Oct 8 - Oct 9
Relais Villa Baldelli
A pool area with lounge chairs, a hot tub, and a view of mountains.
A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.
A spacious room with a large window, a view of a landscape painting, and a desk with a vase of flowers.
A terrace with sun loungers, stone walls, and potted plants.

3. 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.
P16,915
P19,172 total
includes taxes & fees
Oct 25 - Oct 26
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 stone building with a red awning, potted plants, and a staircase leading to the entrance.
A balcony with a table and chairs, a potted plant, and a view of a green landscape.

4. 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.
P24,198
P26,900 total
includes taxes & fees
Nov 2 - Nov 3
Il Falconiere - Relais e Chateaux
A tranquil sunset over a calm body of water with a gazebo structure in the foreground.
An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.
A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.
A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.

5. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
  • Elegant farmhouse pool retreat immerses guests in the Tuscan countryside with dining steps away.
P9,420
P10,716 total
includes taxes & fees
Oct 8 - Oct 9
Cortona Resort - Le Terre Dei Cavalieri
A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, set against a backdrop of trees and a clear sky.
A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.
A stone building with multiple windows and a courtyard.
A stone building with a tiled roof, a small window, and a metal fence.

6. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
  • Immerse in a seasonal poolside paradise with loungers, umbrellas, and fitness amenities.
P8,274
P9,667 total
includes taxes & fees
Oct 15 - Oct 16
Villa Borgo San Pietro
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 greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.

7. 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.
P6,355
P7,414 total
includes taxes & fees
Oct 12 - Oct 13
La Cantina Relais - Fattoria Il Cipresso
A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.
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.
An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.

8. Hotel Le Capanne

Hotel Le Capanne
Arezzo
  • Splash into seasonal bliss at this 24-hour rural pool escape with mountain views and refreshing freedom.
P6,632
P7,717 total
includes taxes & fees
Oct 18 - Oct 19
Hotel Le Capanne
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A person in a white robe standing by a window with a view of mountains.
A bedside table with a vase of flowers, a book, and a drawer.
A couple dining at a table with a scenic view of mountains and a lake.

9. Locanda agli Amici

Locanda agli Amici
Cortona
  • Discover seasonal poolside bliss with rooftop views, sun loungers, and umbrellas at this upscale family-friendly retreat.
P6,150
P7,330 total
includes taxes & fees
Oct 11 - Oct 12
Locanda agli Amici
A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.
A bedroom with a bed, a table with lemons, a window with curtains, and a radiator.
A cozy living room with a fireplace, a sofa, a dining table, and various decorative items.
A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.

10. Locanda del Molino

Locanda del Molino
Cortona
  • Take a dip in the outdoor pool surrounded by Tuscan scenery while sipping refreshing drinks from the poolside bar.
P4,837
P5,886 total
includes taxes & fees
Oct 27 - Oct 28
Locanda del Molino
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

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"
lynda 3-night trip
Posted 2 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"I highly recommend this place Nice place with high trained staff Very clean rooms"
Bahram Ron 3-night trip
Posted 3 days ago
Relais Villa Grazianella - UNA Esperienze
Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"Personal, muy amable y educado, muy cálida, recepción, lindo hotel. Lo aconsejo para quienes quieran visitar la toscana y sobretodo Montepulciano."
Julio 1-night trip
Posted 10 days ago
Hotel Villa Ricci
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 13 days ago
Hotel Corsignano
Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

10/10 Excellent
"buenas vistas panorámicas , es un hotel demasiado tranquilo , pero es muy bonito"
Enzo 2-night trip
Posted 3 weeks ago
Hotel Panoramic Montepulciano

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 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 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 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 sun loungers, an infinity pool, and complimentary wireless internet access.
How many pool hotels can I expect to 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, check out 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 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.

Explore a world of travel with Expedia