TOP Hotels with Pool in Castiglion Fiorentino for 2026

Q: 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.

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 prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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.

1. Hotel Park

Castiglion Fiorentino

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

Rp2.182.591 total

includes taxes & fees

8 Nov - 9 Nov

A person in a swimming pool with a view of trees and mountains through a window.

2. Il Falconiere - Relais e Chateaux

Cortona

Luxurious Tuscan retreat offers twin outdoor pools, winery access, and poolside dining with stunning vineyard views.

Rp5.759.018 total

includes taxes & fees

22 Nov - 23 Nov

A pool area with lounge chairs, a hot tub, and a view of mountains.

3. 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.

Rp4.953.408 total

includes taxes & fees

29 Nov - 30 Nov

A landscaped garden with a swimming pool, neatly trimmed hedges, and outdoor seating areas.

4. La Cantina Relais - Fattoria Il Cipresso

Arezzo

Discover a Tuscan escape with a vineyard-view pool, winery tours, and farm-to-table dining.

Rp2.121.252 total

includes taxes & fees

8 Nov - 9 Nov

A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.

5. Hotel Le Capanne

Arezzo

Splash into seasonal bliss at this 24-hour rural pool escape with mountain views and refreshing freedom.

Rp2.241.230 total

includes taxes & fees

22 Nov - 23 Nov

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

6. Locanda agli Amici

Cortona

Discover seasonal poolside bliss with rooftop views, sun loungers, and umbrellas at this upscale family-friendly retreat.

Rp2.117.315 total

includes taxes & fees

1 Dec - 2 Dec

A swimming pool with a green-lit edge, a glass-enclosed structure in the background, and a bench near the pool.

7. Cortona Resort Spa

Cortona

Serene seasonal outdoor pool awaits at this rural Italian resort, where massages and hiking trails beckon.

Rp3.136.819 total

includes taxes & fees

8 Nov - 9 Nov

A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.

8. Relais La Corte dei Papi

Cortona

Luxurious Tuscan retreat offers poolside bliss with mountain views and spa treatments.

Rp6.535.591 total

includes taxes & fees

18 Nov - 19 Nov

9. iConic Wellness Resort

Arezzo

Rp1.601.992 total

includes taxes & fees

8 Nov - 9 Nov

A modern indoor pool area with lounge chairs and a central hot tub.

10. A Point Arezzo Park Hotel

Arezzo

Serene outdoor pool escape with poolside cocktail bar and loungers creates the perfect Italian countryside retreat.

Rp1.970.534 total

includes taxes & fees

29 Nov - 30 Nov

View all properties

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

Breakfast included

4 stars

Top Castiglion Fiorentino Hotel Reviews

La Cantina Relais - Fattoria Il Cipresso

Arezzo

10/10 Excellent

Ronald

Locanda agli Amici

Cortona

10/10 Excellent

Our overall experience at this hotel has been amazing from start to finish, Silvia make us feel so welcome and went out of her way to make our stay one we will remember. At check in I mentioned I was gluten intolerance the next day at breakfast there was a homemade GF cake. So helpful with local information. Our room was spacious and the bathroom had an amazing shower all cleaned to a high standard. Beautiful pool and terrance area. We will be going back.

Sarah

Monastero di Cortona Hotel & Spa

Cortona Old Town

10/10 Excellent

What a beautiful hotel, the room was spacious clean and extremely well presented. All the staff were so friendly and helpful and made us feel so welcome. The breakfast was delicious and facilities great too. I loved the personal touches like the biscuits and water in the room with a note on arrival and also on the last day. We would highly recommend this hotel to anyone and thoroughly enjoyed our stay here!! :-)

Julie

A villa with a swimming pool, surrounded by olive groves and fields.

Agriturismo Podere Caggiolo

Marciano della Chiana

10/10 Excellent

Guido

A swimming pool with a wooden deck and white pebbles.

DormiVeglia B&B

Monte San Savino

10/10 Excellent

No pictures can justify the beauty, the comfort and elegance of this place! Simona and her family are great hosts and I felt that everything about our stay had us in mind and we were certainly placed in the centre of attention. There were so many little finishing touches, that contributed towards the authentic Tuscan experience starting from the location, the buiding and of course The Breakfast! Amazing coffee to start with, followed by selection of fruit, homemade cakes, biscuits, yogurts ,...

Bela

Il Falconiere - Relais e Chateaux

Cortona

10/10 Excellent

Malcolm

A swimming pool surrounded by a well-maintained lawn, with a fountain in the foreground and a building in the background.

Agriturismo Villa Augusto

Cortona

10/10 Excellent

A first class welcome on arrival, an outstanding property, pool and location in the foothills of Cortona everything exceeded our expectations. The two bedroomed deluxe villa property set in the grounds of the main country house is very spacious, spotlessly clean and very well maintained.lt was perfect for our stay. The owners are friendly and hardworking with nothing too much trouble to enhance your stay. The large pool and sun lounge area surrounded by fig plum and peach trees is perfect for...

Kathryn

Agriturismo Parco Fiorito

Tuoro sul Trasimeno

10/10 Excellent

Anonymous traveller

A swimming pool with a breakfast tray of fruits and juice, surrounded by trees and a clear sky.

B&B Country House Poggio del Drago

Civitella in Val di Chiana

10/10 Excellent

My husband and I had a wonderful stay at Poggio del Drago - Emanuele is a perfect host and made us feel very welcome throughout our stay. The room itself was lovely - recently renovated and looking lovely. The pool is perfectly located, overlooking the olive groves and with plenty of loungers for all guests. Breakfast was great - a large breakfast table where all guests sat together and took breakfast - an array of sliced meats, cereals, and also a coffee machine to make yourself a cappuccino or...

katy

A stone villa with a swimming pool, outdoor seating, and a well-lit patio area.

Chimera Tuscany Resort

Arezzo

10/10 Excellent

Robert

A serene pool area with a clear sky and a distant mountain range.

Agriturismo Antica Corte

Montepulciano

10/10 Excellent

Farah

A nighttime swimming pool with stone buildings in the background.

B&B Le Caselle

Lucignano

10/10 Excellent

Super miejsce, pokój idealny dla dwojga, w łazience wszystko co niezbędne, codziennie typowe włoskie śniadanie, brakowało mi jajek i omletów, ale każdego dnia było pyszne prosciutto, rogaliki, domowe dżemy, owsianka i owoce Zawsze możesz liczyć na pyszną kawę przygotowaną przez gospodarza. Oprócz poniedziałku, możesz być na miejscu w restauracji degustować lokalne toskańskie jedzenie i wino. A wszystko było pyszne. wszystko to dostępne było w rodzinnym hotelu otoczonym zielenią, którą każdego...

Tomasz

A rectangular swimming pool with a tiled deck, surrounded by lounge chairs and umbrellas.

Podere La Rocca

Montepulciano

10/10 Excellent

Giovanni

Frequently Asked Questions

How many pool hotels will I find in Castiglion Fiorentino?

Expedia has 11 hotels in Castiglion Fiorentino for your poolside break.

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.

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.

Search Hotels with Pool in Castiglion Fiorentino

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castiglion Fiorentino hotels with a pool

1. Hotel Park

2. Il Falconiere - Relais e Chateaux

3. Monastero di Cortona Hotel & Spa

4. La Cantina Relais - Fattoria Il Cipresso

5. Hotel Le Capanne

6. Locanda agli Amici

7. Cortona Resort Spa

8. Relais La Corte dei Papi

9. iConic Wellness Resort

10. A Point Arezzo Park Hotel

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

Top Castiglion Fiorentino Hotel Reviews

La Cantina Relais - Fattoria Il Cipresso

10/10 Excellent

Frequently Asked Questions

How many pool hotels will I find in Castiglion Fiorentino?

What's it like visiting Castiglion Fiorentino?

What are some accommodation options with pools in Castiglion Fiorentino?

What is there to see and do in Castiglion Fiorentino?

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

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