The Best Hotels with a Pool in Montecastelli from NT$2,539 in 2026

Q: What are some accommodations with pools in Montecastelli?

Hotel Toscana Ambassador : Offers a snack bar/deli, a seasonal outdoor pool, and free self parking. Hotel Casolare Le Terre Rosse : Provides a snack bar/deli, 3 outdoor pools, and free self parking. Poderi Arcangelo : Hotel located near Siena Cathedral. Offers a children's pool, a seasonal outdoor pool, and free self parking. Hotel Italia : Features 2 restaurants, a pool, and a full-service spa. Villa Ermellina Siena, a Tribute Portfolio Hotel : Offers a children's pool, a seasonal outdoor pool, and a rooftop terrace.

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Our top choices for Montecastelli hotels with a pool

Outdoor pool, free cabanas, pool umbrellas

Borgo Santo Pietro

Chiusdino

Tuscan oasis boasts poolside luxury with cabanas, spa treatments, and hot tub escapes.

NT$137,577 total

includes taxes & fees

Jun 4 - Jun 5

Villa Sabolini

Colle di Val d'Elsa

Sunshine dances across the tranquil outdoor pool at this historic Tuscan villa.

NT$6,049 total

includes taxes & fees

Jun 21 - Jun 22

Hotel Casolare Le Terre Rosse

San Gimignano

Dive into a sparkling oasis with loungers and umbrellas at this seasonal pool sanctuary.

NT$6,947 total

includes taxes & fees

Jun 28 - Jun 29

Agriturismo Il Cerreto

Pomarance

Tuscan farm offers seasonal outdoor pool with loungers, children's pool, and hill views for pure bliss.

NT$5,846 total

includes taxes & fees

Jun 25 - Jun 26

Castello di Casole, A Belmond Hotel, Tuscany

Casole d'Elsa

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

NT$82,126 total

includes taxes & fees

Jun 11 - Jun 12

Seasonal outdoor pool, pool umbrellas, sun loungers

Residence Il Paradiso

Guardistallo

Splash into serenity at this Tuscan oasis, where poolside lounging meets rural charm.

NT$2,539 total

includes taxes & fees

Jun 2 - Jun 3

Riserva di Fizzano Residence

Castellina in Chianti

Vineyard retreat's outdoor pool offers tranquil relaxation with Tuscan sunshine and idyllic views.

NT$8,021 total

includes taxes & fees

Jun 10 - Jun 11

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.

NT$23,950 total

includes taxes & fees

Jun 26 - Jun 27

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Choose what matters most at hotels with a pool in Montecastelli

Breakfast included

4 stars

Top Montecastelli Hotel Reviews

Hotel Italia

10/10 Excellent

"Great place if you want to stay right outside the ZTL zone and the wall (beware of that if you are driving). Such a gem of hotel. The staff was super helpful, very kind and serviceable, i mean really really really nice. The room was a little tight for 4, but the bathroom was huge! All super clean, really impeccable. Our bedroom was in the adjacent building but in the ground floor, which made rolling in the luggage a breeze. The room itself had a queen bed and a day bed with a trundle. They were so nice and had the beds made for 4 when we arrived, i.e. they took out the trundle and made the bed as well as the daybed. I yet have to see that happen in the US... very attentive to detail. A very very minor thing, but the bed covers should be updated to be a bit more modern, looked like my grandma's curtains. Nevertheless, it was perfect for one night and also greatly appreciated the AC. The brick ceilings were also very charming. The breakfast buffet is absolutely amazing! Well worth the stay. They also have parking, but you need to reserve it ahead. We had gotten an email a couple of days before, but bc we were traveling around, I missed their ask if we wanted parking. Nevertheless, we found parking right behind the building so didn't matter at all, but you need to ask ahead for parking as they have limited spots A walk to the center if town is about 20mn and very easy stroll. This place is just perfect!! And Siena is just one of my favorite cities in Italy!!! Perfect combo!"