The Best Hotels with a Pool in Casole d'Elsa in 2026

A cobblestone street with historic buildings, a wooden chair, and potted plants.

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Our top choices for Casole d'Elsa hotels with a pool

Castello di Casole, A Belmond Hotel, Tuscany

Casole d'Elsa

A dreamy Tuscan poolside escape where luxury meets Italian countryside charm.

₩3,161,905 total

includes taxes & fees

Aug 14 - Aug 15

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Relax Hotel Acquaviva

Casole d'Elsa

₩194,785 total

includes taxes & fees

Jul 27 - Jul 28

2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, sun loungers

Castiglion del Bosco, A Rosewood Hotel

Montalcino

Poolside bliss awaits at this Tuscan hotel where loungers, umbrellas, and cocktails create a refreshing retreat.

₩2,883,665 total

includes taxes & fees

Aug 2 - Aug 3

3 outdoor pools, pool umbrellas, sun loungers

Borgo Pignano Volterra Tuscany

Volterra

Serene Tuscan getaway with 2 outdoor pools and children's splash zone, nestled near historic San Gimignano landmarks.

₩1,066,283 total

includes taxes & fees

Aug 9 - Aug 10

Hotel Certosa Di Maggiano

Siena

Dive into a sun-drenched paradise with this hotel's stunning outdoor pool, complete with a poolside bar and tennis court nearby.

₩877,848 total

includes taxes & fees

Aug 11 - Aug 12

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.

₩178,774 total

includes taxes & fees

Jul 27 - Jul 28

Pieve Aldina - Relais & Châteaux

Radda in Chianti

Escape to a luxury Tuscan retreat with a seasonal outdoor pool and on-site winery.

₩586,103 total

includes taxes & fees

Jul 26 - Jul 27

Indoor pool, seasonal outdoor pool, sun loungers

Hotel Le Fontanelle

Castelnuovo Berardenga

Dive into tranquil luxury at this hotel's indoor and seasonal outdoor pools, complemented by a poolside bar and loungers.

₩577,304 total

includes taxes & fees

Aug 17 - Aug 18

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Choose what matters most at hotels with a pool in Casole d'Elsa

Breakfast included

4 stars

Top Casole d'Elsa Hotel Reviews

Castelfalfi

10/10 Excellent

"Outstanding hotel"

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"One of my favorite hotels. The rooms (at least ours) are very small. BUT... they're beautiful as is the entire property. It's a hike to town, so plan on driving or taking a cab. The views are incredible. It's the type of hotel experience you would imagine for your Italian dream vacation. Nitpicks: We booked two days in Siena as a rest in the middle of the rest of our travels. This would have been PERFECT for that, except that they were hosting a large, Indian wedding. (Which was BEAUTIFUL by the way.) But, the DJ played (accompanied by a saxophonist!) until almost midnight and the morning ceremony started pretty early as well. So, it didn't end up being as restful as we'd hoped as this was all happening right outside our window. Also, if the restaurant or bar is closed, there is no where to get a snack or drink. (Not really anywhere to get just a snack anyway.) Wouldn't be such a big deal, except you're not near any convenience stories or anything. A vending machine would be nice!"

Poderi Arcangelo

10/10 Excellent

"Our stay here exceeded expectations. Accommodations in the main building were rustic but very well maintained, and with modern amenities. It had a “small resort feel” to it. We did not visit the other buildings but safe to assume the same. Staff were very friendly and helpful. They arranged cooking classes, wine tours and helped us organize a local horseback trail ride. The main pool can get busy. Certainly not a complaint - if you’re looking to be social with others I recommend it, but if looking for a quieter setting, the detached buildings with their own pools looked quieter. You can’t always get a drink or food during the day and the reception area does close so pay attention to their hours. There is a fridge on site for guests to store some snacks and beverages. The patio, where food is served (both inside and outside options available - inside has unobstructed views). Breakfast buffet is served daily - European style, lunch needs to be pre-ordered daily and supper reservations are needed by mid afternoon. We also found guest laundry on site - washer only though. Defenitely need a car to get around the site and to tour the area. Groceries and restaurant options are a 10-20 mins drive away in smaller towns. There are multiple gathering points where you can hang out as a family or group on site. We felt we had a true Italian experience while staying here."

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

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Our top choices for Casole d'Elsa hotels with a pool

Castello di Casole, A Belmond Hotel, Tuscany

Relax Hotel Acquaviva

Castiglion del Bosco, A Rosewood Hotel

Borgo Pignano Volterra Tuscany

Hotel Certosa Di Maggiano

Agriturismo San Sano

Pieve Aldina - Relais & Châteaux

Hotel Le Fontanelle

Choose what matters most at hotels with a pool in Casole d'Elsa

Top Casole d'Elsa Hotel Reviews

Castelfalfi

Castello di Casole, A Belmond Hotel, Tuscany

Hotel Athena

Villa Ermellina Siena, a Tribute Portfolio Hotel

Hotel Casolare Le Terre Rosse

Poderi Arcangelo

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Leonina Relais

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Find Hotels with a Pool in Casole d'Elsa

Change your mind

Treat yourself

Be picky

Check availability on Casole d'Elsa Hotels with a Pool

Our top choices for Casole d'Elsa hotels with a pool

Castello di Casole, A Belmond Hotel, Tuscany

Relax Hotel Acquaviva

Castiglion del Bosco, A Rosewood Hotel

Borgo Pignano Volterra Tuscany

Hotel Certosa Di Maggiano

Agriturismo San Sano

Pieve Aldina - Relais & Châteaux

Hotel Le Fontanelle

Choose what matters most at hotels with a pool in Casole d'Elsa

Top Casole d'Elsa Hotel Reviews

Castelfalfi

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