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Check availability on Cavallari Hotels with Pool

Tonight
23 Sep - 24 Sep
Tomorrow
24 Sep - 25 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Cavallari hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.
A stone building with a courtyard, a covered seating area, and a small bell tower.
A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.
A cozy living room with a stone fireplace, striped sofas, and a coffee table.

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
฿2,978
฿3,427 total
includes taxes & fees
14 Oct - 15 Oct
Borgo di Pietrafitta Relais
A clear blue pool with lounge chairs and a stone building in the background.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A stone building with a wooden bench outside.

2. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
฿4,146
฿4,674 total
includes taxes & fees
18 Oct - 19 Oct
Hotel Colle Etrusco Salivolpi
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A building with arched windows, a courtyard with a pond, and a metal fence.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.

3. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
  • Sun-soaked seasonal pool oasis in the heart of a Tuscan wine resort with loungers and umbrellas.
฿2,044
฿2,477 total
includes taxes & fees
27 Sept - 28 Sept
Hotel Casafrassi
A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.
A cozy living room with two beige sofas, a glass coffee table, and a patterned rug.

4. 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.
฿6,711
฿7,610 total
includes taxes & fees
21 Oct - 22 Oct
Palazzo Squarcialupi
A pool surrounded by lush greenery and vineyards, with a stone building in the background.
A stone building with a window and a light fixture.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

5. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
  • Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.
฿2,461
฿2,859 total
includes taxes & fees
18 Oct - 19 Oct
Agriturismo San Sano
A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.
An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.
A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

6. 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.
฿6,051
฿6,884 total
includes taxes & fees
20 Oct - 21 Oct
Hotel Villa Campomaggio
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.
A restaurant with a table set for two, overlooking a scenic landscape.
An outdoor dining area with a pool, potted plants, and umbrellas.

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.
฿5,845
฿7,594 total
includes taxes & fees
8 Oct - 9 Oct
Relais Vignale & Spa
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.
An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

8. Borgo Vescine

Borgo Vescine
Radda in Chianti
  • Slip into Tuscan bliss at this pool paradise with vineyard views and poolside bar service.
฿17,495
฿19,548 total
includes taxes & fees
20 Oct - 21 Oct
Borgo Vescine
A poolside area with lounge chairs and a view of the night sky.
A rustic stone building with a garden in front.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

9. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
฿4,122
฿4,761 total
includes taxes & fees
15 Oct - 16 Oct
Belvedere di San Leonino
A spa area with a stone ceiling, a pool, and two sun loungers.
A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.
A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.
A modern bathroom with a freestanding bathtub, a vanity with a mirror, and marble walls.

10. Hotel Palazzo San niccolò & Spa

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.
฿5,029
฿5,760 total
includes taxes & fees
28 Sept - 29 Sept
Hotel Palazzo San niccolò & Spa
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

10/10 Excellent
"Location is beautiful. We were in the separate house."
Guillermo 3-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 7 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 8 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 8 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 11 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 3 weeks ago
Borgo San Felice Resort

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 a full-service spa, an outdoor pool and a sauna. NH Siena: Hotel located near Piazza del Campo. Provides a rooftop terrace, a seasonal outdoor pool and a snack bar/deli.
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.

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