Top 10 Hotels with Pool & Accommodation in Montecastelli from NZ$177 | Expedia

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Check availability on Montecastelli Hotels with Pool

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10 Jul - 12 Jul

Next weekend

17 Jul - 19 Jul

Our top choices for Montecastelli hotels with a pool

Exterior

Villa Sabolini

Colle di Val d'Elsa

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

includes taxes & fees

7 Aug - 8 Aug

Seasonal outdoor pool, pool loungers

Hotel Borgo San Luigi

Monteriggioni

Take a dip in crystal waters as Tuscan countryside surrounds the seasonal pool.

includes taxes & fees

15 July - 16 July

Exterior

Hotel Casolare Le Terre Rosse

San Gimignano

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

includes taxes & fees

19 July - 20 July

Outdoor banquet area

Castello di Casole, A Belmond Hotel, Tuscany

Casole d'Elsa

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

includes taxes & fees

14 July - 15 July

Outdoor pool, free pool cabanas, pool umbrellas

Borgo Santo Pietro

Chiusdino

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

includes taxes & fees

4 Aug - 5 Aug

Outdoor pool, pool umbrellas, pool loungers

Riserva di Fizzano Residence

Castellina in Chianti

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

includes taxes & fees

10 July - 11 July

Seasonal outdoor pool, open 7 AM to 8:30 PM, pool umbrellas

Villa San Lucchese

Poggibonsi

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

includes taxes & fees

12 July - 13 July

Seasonal outdoor pool, pool umbrellas, pool loungers

Hotel Il Piccolo Castello

Monteriggioni

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

includes taxes & fees

12 July - 13 July

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Choose what matters most at hotels with a pool in Montecastelli

Breakfast included

4 stars

Top Montecastelli Hotel Reviews

Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"Perfect location to unwind after a day in the heat. Walk into centre 25 min. Staff was very friendly and helpful. Would definitely recommend staying here"

Villa Sabolini

Villa Sabolini

10/10 Excellent

"We came to this hotel unexpectedly and were so happy we found it. The staff are truly exceptional, friendly, attentive, accommodating, effective, welcoming. We arrived due to my wife having emergency surgery in Siena, we were supposed to be in Venice, and this hotel staff went to work making sure we were taken care of. The grounds are stunning as well, an amazing place to recover after surgery. The pool is beautiful and the restaurant is fantastic. I truly have enjoyed each meal I have had. The lunch I ordered of sliced beef with rocket, pecorino and tomato was perfectly cooked and so tasty. The bartender Bruno makes a fantastic Negroni and I have had the chance to taste it with 3 different small gins all from this region. The front office staff from Silvia, Valentina and each person we interacted with have been amazing. We were looking forward to the basset hounds as well, we have seen them lounging about but hope to get to meet them before our stay ends. A wonderful place to stay in the Tuscan countryside, and only a 20 minute drive to Siena."

Hotel Italia

Hotel Italia

10/10 Excellent

"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the A/C worked perfectly; we didn’t hear a sound from neighbors or stair traffic. The location is a sweet spot — only 5 to 10 minutes from the tourist sights, yet tucked in a local neighborhood with bakeries and grocery stores, giving us that refreshing, peaceful feeling of being disconnected from the tourist rush. Breakfast was amazing, and the little teen-approved Duomo and gelato challenges made exploring even more fun. Bottom line: we’d come back and stay here again in a heartbeat. For anyone visiting Siena, Hotel Italia at Porta Camollia gives you that perfect “live like a local” buffer before diving into the Duomo and Piazza del Campo — and if you need a salon, just ask reception; their pick is solid."

Frequently asked questions

What are some accommodation options with pools in Montecastelli?

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

What is there to see and do in Montecastelli?

Make a point to visit attractions such as Alta Val d'Elsa River Park and Terre di Vini. Discover sights such as Medici Fortress, Porta all'Arco and Palazzo dei Priori during your stay.

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

You may want to consider a place to stay that offers an outdoor pool if you're planning to visit Montecastelli in the hottest months of August, July or June, when the average temperature is 22°C. Accommodation with an indoor pool may be the way to go if you visit during the coldest months of January, February or December, when the average temp is 6°C.

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