TOP Hotels with Pool in Penna for 2026

Q: What are some accommodation options with pools in Penna?

Borgo Scopeto Wine & Country Relais : Features 2 restaurants, 2 outdoor swimming pools and a full-service spa. A Point Arezzo Park Hotel : Offers 2 restaurants, a seasonal outdoor pool and a full-service spa. La Certosa di Pontignano : Features 2 restaurants, a seasonal outdoor pool and a full-service spa. Borgo San Felice Resort : Offers a seasonal outdoor pool, an indoor pool and 2 restaurants. Villa Casagrande Resort & SPA : Features an indoor pool, an outdoor pool and 2 restaurants.

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Our top choices for Penna hotels with a pool

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.

฿4,888 total

includes taxes & fees

19 Jul - 20 Jul

Chapter Chianti, a Member of Design Hotels

Cavriglia

฿11,323 total

includes taxes & fees

1 Aug - 2 Aug

2 outdoor pools, pool umbrellas, pool loungers

Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Float in tuscan splendour with vineyard views from two pools at this wine country hotel.

฿18,509 total

includes taxes & fees

2 Aug - 3 Aug

Castello di Meleto

Gaiole in Chianti

Seasonal outdoor pool at Tuscan farm stay with vineyard views and sun loungers for serene relaxation amid the countryside.

฿8,803 total

includes taxes & fees

7 Aug - 8 Aug

Dievole Wine Resort

Castelnuovo Berardenga

Splash into luxury at a Tuscan wine resort with two outdoor pools and vineyard views.

฿13,557 total

includes taxes & fees

2 Aug - 3 Aug

Torre a Cona Wine Estate

Rignano sull'Arno

Seasonal vineyard splash awaits with mountain views and winery moments.

฿12,347 total

includes taxes & fees

24 Jul - 25 Jul

Castello di Tornano Wine Resort

Gaiole in Chianti

Poolside bliss awaits at this Tuscan wine resort where medieval castle meets vineyard views.

฿8,497 total

includes taxes & fees

6 Aug - 7 Aug

Seasonal outdoor pool, free pool cabanas, pool umbrellas

Borgo San Felice Resort

Castelnuovo Berardenga

Experience a luxury wine country retreat with a seasonal outdoor pool, poolside cabanas, and an indulgent on-site spa.

฿26,946 total

includes taxes & fees

9 Aug - 10 Aug

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Choose what matters most at hotels with a pool in Penna

Breakfast included

4 stars

Top Penna Hotel Reviews

Castello Vicchiomaggio

10/10 Excellent

"A true oasis in Tuscany, large rooms with every needed amenity, fantastic pool overlooking the vineyards"

Hotel Le Fontanelle

10/10 Excellent

"The photos might hint at the quality of the property but don’t really do it justice. The sweeping easterly, vineyard views across to Monti-in-Chianti and up to Brolio are really mesmerizing. Grounds were well kept. Breakfast had the usual Italian selection of good fruits, grains, meats, breads, and sweets. Coupled with a limited menu of ala carte items and rich cappuccinos! Our suite was located about .25mi south of the main building. We enjoyed the walk multiple times per day but grandma might not. The room was nicely appointed with a living room, large bedroom, closet space and two sink bathroom. Stocked mini-fridge and cof/tea selections. Each room had its own outdoor area with a table/chaise to enjoy with coffee or after the pool. The out door pool is not heated (indoor pool is) but very comfortable on the 90 degree days we spent there. Pool service isn’t quite the same as some resorts, as you would go to the bar to order food/beverage and they’d bring it out to your chair setup. A good selection of menu items are available to choose from. Restaurants on site were excellent. Had the Bistecca at Tuscanio and it was perfection while LaColonna’s carpaccio and fusilli dish were both a treat. Staff was friendly though a bit harried. Seemed like they just needed a few more bodies around to smooth out the place. Ilaria at the front desk was really outstanding with her command and knowledge. While Marcella really made the pool with her wry smile and daily daiquiri selection."

Dievole Wine Resort

10/10 Excellent

"Our stay at this Tuscan wine resort was nothing short of magical. Surrounded by stunning vineyards and ancient olive groves, the property is impeccably maintained and exudes refined, quiet elegance. The rooms and dining areas are spotless and sophisticated, providing the perfect backdrop for the truly elevated, delicious meals we enjoyed. The service was exceptional throughout, with a special thank you to Veronica and Gianluca, whose warmth and impeccable care made our experience unforgettable. This is the ultimate Tuscan escape— we cannot wait to return!"

Hotel Villa Campomaggio

10/10 Excellent

"I was fortunate enough to stay in this beautiful hotel whilst photographing a wedding in Tuscany and I was so pleased that I am hoping to stay again as soon as I can. The staff were lovely, the hotel was beautiful and the surrounding areas were stunning. The spa was clean and calming, with three different rooms to try and a jacuzzi. I was offered a free yoga class one morning and my room was cleaned before 10am every day. On my last day, I checked out at 11am after breakfast and was offered a place to keep my bags so that I could stay out by the pooI until I needed to leave. I would highly recommend this beautiful hotel to anyone travelling through Tuscany!"

Frequently asked questions

What are some accommodation options with pools in Penna?

Borgo Scopeto Wine & Country Relais: Features 2 restaurants, 2 outdoor swimming pools and a full-service spa. A Point Arezzo Park Hotel: Offers 2 restaurants, a seasonal outdoor pool and a full-service spa. La Certosa di Pontignano: Features 2 restaurants, a seasonal outdoor pool and a full-service spa. Borgo San Felice Resort: Offers a seasonal outdoor pool, an indoor pool and 2 restaurants. Villa Casagrande Resort & SPA: Features an indoor pool, an outdoor pool and 2 restaurants.

What is there to see and do in Penna?

Make a point to visit attractions such as Piazza Guido Monaco and Fattoria La Vialla. Discover sights such as San Pietro a Gropina, Croce del Pratomagno and Franciscan Monastery of St. Francis during your stay.

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

You may want to think about a place to stay that has an outdoor pool if you plan to visit Penna in the warmest months of August, July or June, when the average temp is 22°C. Accommodation offering 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 6°C.

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