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Find Hotels with a Pool in Cavallari

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Check availability on Cavallari Hotels with a Pool

Tonight
Sep 20 - Sep 21
Tomorrow
Sep 21 - Sep 22
Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for Cavallari hotels with a pool

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
¥13,110
¥15,143 total
includes taxes & fees
Oct 19 - Oct 20
Borgo di Pietrafitta Relais

2. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
¥18,914
¥21,346 total
includes taxes & fees
Oct 7 - Oct 8
Hotel Colle Etrusco Salivolpi

3. Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
  • Dive into the tranquil waters of a seasonal outdoor pool surrounded by the charm of this Beaux Arts hotel and attached winery.
¥30,961
¥35,138 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi

4. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
  • Soak in mountain views from the sun-drenched outdoor pool at this Tuscan retreat where spa treatments and regional cuisine await.
¥28,756
¥32,713 total
includes taxes & fees
Oct 20 - Oct 21
Hotel Villa Campomaggio

5. Borgo Vescine

Borgo Vescine
Radda in Chianti
  • Slip into Tuscan bliss at this pool paradise with vineyard views and poolside bar service.
¥76,492
¥85,582 total
includes taxes & fees
Oct 21 - Oct 22
Borgo Vescine

6. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
  • Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.
¥10,878
¥12,687 total
includes taxes & fees
Oct 21 - Oct 22
Agriturismo San Sano

7. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
  • Discover a seasonal rooftop sanctuary with dual pools, poolside bar service, and stunning vineyard views in historic wine country.
¥25,819
¥33,933 total
includes taxes & fees
Oct 13 - Oct 14
Relais Vignale & Spa

8. Castello La Leccia

Castello La Leccia
Castellina in Chianti
  • Castello La Leccia's seasonal pool offers Tuscan countryside refreshment and vineyard views all summer long.
¥43,440
¥48,505 total
includes taxes & fees
Oct 17 - Oct 18
Castello La Leccia

9. Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
  • Savor countryside luxury at the outdoor pool, where vineyard views and poolside cocktails create an idyllic Tuscan escape.
¥58,967
¥65,944 total
includes taxes & fees
Sep 28 - Sep 29
Locanda le Piazze

10. Villa Le Barone

Villa Le Barone
Greve in Chianti
  • Dive into luxury at this Tuscan retreat with 2 outdoor pools, mountain views, and a poolside bar for ultimate relaxation.
¥40,762
¥45,919 total
includes taxes & fees
Oct 11 - Oct 12
Villa Le Barone
View all properties

Choose what matters most at hotels with a pool in Cavallari

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Cavallari Hotel Reviews

Poderi Arcangelo

Poderi Arcangelo

8/10 Good
"The room had very little of the basic necessities. On arrival we had to carry all our luggage up a steep slope and climb stairs with no railings for leverage."
Bruno 7-night trip
Posted 2 days ago
Poderi Arcangelo
Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"The villa is amazing and the perfect little world in itself. Its closeness to Siena makes it easier to visit the city. The patio is the perfect place to view Siena at sunset. The staff was very courteous and ready to help. This hotel is a gem."
Federica 1-night trip
Posted 4 days ago
Villa Scacciapensieri Boutique Hotel
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"If you are driving around in Tuscany and need a place to stay, look no further! The place is beautiful, clean, friendly staff and feels like a 5 star hotel without the price. location was central to all the wineries and Tuscany sites. Breakfast was fantastic. Awesome place!"
George 1-night trip
Posted 5 days ago
Hotel Casolare Le Terre Rosse
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."
David 3-night trip
Posted 5 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 8 days ago
Hotel Italia
Borgo San Felice Resort

Borgo San Felice Resort

10/10 Excellent
"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"
Yael 2-night trip
Posted 2 weeks ago
Borgo San Felice Resort

Frequently asked questions

What are some accommodations 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 center. La Certosa di Pontignano: Provides a rooftop terrace, an outdoor pool, and a snack bar/deli. Hotel Athena: Features a snack bar/deli, 3 outdoor pools, and free self parking. Hotel Executive: Offers a full-service spa, an outdoor pool, and a sauna. NH Siena: Provides sun loungers, a pool, and complimentary wireless internet access.
What is there to see and do in Cavallari?
Make a point to visit attractions like Arno River and Borgo di Vescine - Tenute di Castelvecchi. During your stay, check out 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 with an outdoor swimming pool if you will be visiting Cavallari in the hottest months of August, July, or June when the average temperature is 72°F. Lodging offering 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 44°F.

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