The Best Hotels with a Pool in Montecastelli from AED 334 in 2026

Q: What are some accommodations 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 pools, and free self parking. Hotel Casolare Le Terre Rosse : Offers 2 restaurants, a pool, and a full-service spa.

Check availability on Montecastelli Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Montecastelli hotels with a pool

Outdoor pool, pool umbrellas, sun loungers

Dojo Bianco

Massa Marittima

AED 1,155 total

includes taxes & fees

1 Aug - 2 Aug

Hotel Duca Del Mare

Massa Marittima

Seasonal outdoor pool beckons with summer splashes and city center relaxation.

AED 453 total

includes taxes & fees

7 Jul - 8 Jul

Hotiday Massa Marittima

Massa Marittima

AED 462 total

includes taxes & fees

9 Jul - 10 Jul

Seasonal outdoor pool, pool umbrellas, sun loungers

Hotel Girifalco - Nature & Relax

Massa Marittima

Dive into a refreshing poolside escape where seasonal swimming meets gorgeous garden views at this bed & breakfast.

AED 334 total

includes taxes & fees

12 Jul - 13 Jul

Country House il Ciliegio

Roccastrada

Tuscan paradise awaits with private poolside bar service and children's splash area.

AED 459 total

includes taxes & fees

7 Jul - 8 Jul

Valdonica Winery - Chill in Nature Lodge

Roccastrada

Wine country retreat with a seasonal outdoor pool and on-site vineyard makes for a splendid Tuscan escape.

AED 761 total

includes taxes & fees

21 Jul - 22 Jul

Valdonica Winery & Vineyard Residence

Roccastrada

Swim in Tuscan splendor at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.

AED 603 total

includes taxes & fees

26 Jul - 27 Jul

Il Belvedere Country Houses

Massa Marittima

Dive into countryside relaxation with seasonal poolside charm and rural scenic views.

AED 499 total

includes taxes & fees

9 Jul - 10 Jul

View all properties

Choose what matters most at hotels with a pool in Montecastelli

Breakfast included

4 stars

Top Montecastelli Hotel Reviews

Hotel Sovestro

10/10 Excellent

"We stayed for one night, wished we had booked a longer stay. Peaceful setting, beautiful outdoor dining area and just a few minutes from San Gimigano."

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

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."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Everything was great! The location, the pool and grounds, food and beverage were wonderful. The staff was very helpful. It was a great benefit to be able to do a load of laundry. Our only suggestion would be to add another set of machines, as it gets busy but thankful to have it."

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations 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 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 like 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 plan to visit Montecastelli in the hottest months of August, July, or June when the average temp is 72°F. Lodging 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 44°F.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Montecastelli Hotels with a Pool