TOP Hotels with Pool in Cavallari for 2026

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

Radisson Blu Hotel, Florence : Hotel located near Ponte Vecchio. Features free self parking, an outdoor pool and a 24-hour fitness centre. La Certosa di Pontignano : Provides a snack bar/deli, 3 outdoor swimming pools and free self parking. Hotel Athena : Offers a rooftop terrace, an outdoor pool and a snack bar/deli. Hotel Executive : Offers an indoor pool, an outdoor pool and 2 restaurants. NH Siena : Villa located near Ponte Vecchio. Provides an infinity pool, an outdoor pool and a water park.

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Our top choices for Cavallari hotels with a pool

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

1. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Sun-kissed pools in tuscan splendour beckon with historic charm and breathtaking views.

Rp2.220.522 total

includes taxes & fees

13 Dec - 14 Dec

A resort with a swimming pool, terraced gardens, and a view of rolling hills.

2. COMO Castello Del Nero

Tavarnelle Val di Pesa

Seasonal outdoor pool oasis in Tuscan wine country offers private poolside dining and luxury spa treatments.

Rp14.473.304 total

includes taxes & fees

20 Nov - 21 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a clear sky.

3. Dievole Wine Resort

Castelnuovo Berardenga

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

Rp5.722.893 total

includes taxes & fees

16 Nov - 17 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a clear sky.

4. Borgo Vescine

Radda in Chianti

Slip into Tuscan bliss at this pool paradise with vineyard views and poolside bar service.

Rp9.291.901 total

includes taxes & fees

22 Nov - 23 Nov

A poolside area with lounge chairs, umbrellas, and a swimming pool.

5. Hotel Il Piccolo Castello

Monteriggioni

Seasonal outdoor pool paradise nestled in rural Italy, where sunny loungers and poolside drinks await amidst Tuscan adventures.

Rp2.350.553 total

includes taxes & fees

15 Nov - 16 Nov

A spa area with a stone ceiling, a pool, and two sun loungers.

6. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Dive into year-round pool perfection with indoor and seasonal outdoor swimming options at this elegant Tuscan retreat.

Rp1.561.426 total

includes taxes & fees

1 Dec - 2 Dec

A pool with a pink flamingo float, surrounded by lounge chairs and a stone deck.

7. La Pensione di Vignamaggio

Panzano in Chianti

Dive into poolside tranquility with a seasonal outdoor pool nestled among gardens and a charming terrace at this Italian retreat.

Rp3.188.705 total

includes taxes & fees

14 Nov - 15 Nov

A poolside setting with a metal tray holding a cocktail glass, a martini glass, and a bottle of BORDO.

8. Belvedere di San Leonino

Castellina in Chianti

Scenic Tuscan escape with a poolside paradise and winery at your doorstep.

Rp2.242.255 total

includes taxes & fees

21 Nov - 22 Nov

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

9. Villa San Lucchese

Poggibonsi

Sun-drenched poolside retreat with waterslide and children's pool awaits at this Tuscan villa.

Rp1.892.480 total

includes taxes & fees

29 Nov - 30 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and trees.

10. Hotel Villa San Giorgio

Poggibonsi

Rp1.087.008 total

includes taxes & fees

13 Dec - 14 Dec

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Choose what matters most at hotels with a pool in Cavallari

Breakfast included

4 stars

Top Cavallari Hotel Reviews

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Jess

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Yoke yin

Borgo Vescine

Radda in Chianti

10/10 Excellent

I'd never heard of Radda before but this place is a gem, just outside of this little Tuscan town. Situated near In Greve, Castellina, and the Chianti road, the service, sights, and grounds are unbelievable. I travelled to this hotel with my parents and we each staying in rooms that felt like separate villas. Theirs had an amazing view and mine had a private porch that was tucked away, perfect for sitting with friends or family to have a late night glassw of wine or cigar. The grounds feel very...

Matt

Villa San Lucchese

Poggibonsi

10/10 Excellent

Anonymous traveller

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

10/10 Excellent

Anonymous traveller

A poolside area with lounge chairs and a large pool, surrounded by well-manicured lawns and tall cypress trees.

One Belvedere Tuscany

Poggibonsi

10/10 Excellent

Such a wonderful long weekend at the belvedere. The property is absolutely beautiful, the location, grounds and view are something to be seen, and the staff very friendly and accommodating. We had not rented a car, and they went above and beyond to assist us with getting around and enjoying events planned on site. Everything felt luxurious, and my partner and I felt more relaxed than we have on any other holiday this year! Recommend to any couple looking for a quiet, romantic trip!

Nicola

A swimming pool with lounge chairs and a pergola, surrounded by a landscaped garden and a view of a forested hillside.

Castello di Volpaia

Radda in Chianti

10/10 Excellent

Tomi

A large villa with a swimming pool, sun loungers, and a well-maintained lawn.

The Club House

Castelnuovo Berardenga

10/10 Excellent

A wonderful stay at The Club House. This is a gorgeous place in a beautiful setting in the heart of Chianti. The property is immaculate, the staff friendly and the food delicious. We have been to wonderful hotels all over the world but this place is really special. It was our second visit (we stayed in August 2025). Everything was great but if I had to be picky I would say the gym is insanely hot in the morning (despite asking for the air con to be put on the evening before). Also, having...

Elizabeth

A hotel room with a large bed, a vanity with a mirror, and a green archway.

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

Lizzy

A balcony with a view of the sunset, a pool, and a metal container with rocks.

Hotel Torciano Vecchio Asilo

San Gimignano

10/10 Excellent

Fantastic hospitality and service. We booked a one night stay (very late as we were at the superb vineyard down the road and arrived after just 2 hours later) but this was no trouble. We were greeted first by the owner's lovely daughter and then the owner who made us feel welcome immediately. The room was basic but very clean and pretty. A nice touch to be able to buy beer, wine, snacks etc. out of hours from the large 'minibar' fridge in the hall ir local chianti in the room. The breakfast was...

Gary

Hotel Il Piccolo Castello

Monteriggioni

10/10 Excellent

Vinay

Frequently Asked Questions

What are some accommodation options with pools in Cavallari?

Radisson Blu Hotel, Florence: Hotel located near Ponte Vecchio. Features free self parking, an outdoor pool and a 24-hour fitness centre. La Certosa di Pontignano: Provides a snack bar/deli, 3 outdoor swimming pools and free self parking. Hotel Athena: Offers a rooftop terrace, an outdoor pool and a snack bar/deli. Hotel Executive: Offers an indoor pool, an outdoor pool and 2 restaurants. NH Siena: Villa located near Ponte Vecchio. Provides an infinity pool, an outdoor pool and a water park.

What is there to see and do in Cavallari?

Make a point to visit attractions such as Arno River and Borgo di Vescine - Tenute di Castelvecchi. During your stay, visit sights such as City Hall Castellina In Chianti, Il Molino di Grace Winery and Castello di Radda Winery.

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

You may want to think about a place to stay that offers an outdoor pool if you plan to visit Cavallari in the hottest months of August, July or June, when the average temperature is 22°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or December, when the average temperature is 6°C.

Search Hotels with Pool in Cavallari

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Check prices for these dates

Our top choices for Cavallari hotels with a pool

1. Palazzo Leopoldo Dimora Storica & Spa

2. COMO Castello Del Nero

3. Dievole Wine Resort

4. Borgo Vescine

5. Hotel Il Piccolo Castello

6. Hotel Palazzo San niccolò & Spa

7. La Pensione di Vignamaggio

8. Belvedere di San Leonino

9. Villa San Lucchese

10. Hotel Villa San Giorgio

Choose what matters most at hotels with a pool in Cavallari

Top Cavallari Hotel Reviews

Belvedere di San Leonino

10/10 Excellent

Frequently Asked Questions

What are some accommodation options with pools in Cavallari?

What is there to see and do in Cavallari?

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