TOP Hotels with Pool in Montecastelli for 2026

Q: What are some accommodation options with pools in Montecastelli?

Hotel Italia : Offers a snack bar/deli, 3 outdoor swimming pools and free self parking. Poderi Arcangelo : Provides a snack bar/deli, a seasonal outdoor pool and free self parking. Hotel Casolare Le Terre Rosse : Hotel located near Piazza del Campo. Features a children's pool, a seasonal outdoor pool and free self parking. Villa Ermellina Siena, a Tribute Portfolio Hotel : Offers a rooftop terrace, 2 outdoor swimming pools and a snack bar/deli. Hotel Sovestro : Features 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

A hotel with a pool, outdoor seating, and a mountainous backdrop.

1. Castello di Casole, A Belmond Hotel, Tuscany

Casole d'Elsa

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

Rp18.679.263 total

includes taxes & fees

20 Nov - 21 Nov

A swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.

2. Villa Sabolini

Colle di Val d'Elsa

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

Rp1.512.349 total

includes taxes & fees

1 Dec - 2 Dec

A swimming pool at night with a stone building in the background.

3. Tenuta Decimo

San Gimignano

Refreshing outdoor pool surrounded by Tuscan beauty awaits at this farm stay near San Gimignano's historic palace.

Rp1.654.103 total

includes taxes & fees

18 Nov - 19 Nov

A poolside area with lounge chairs, umbrellas, and a swimming pool.

4. Hotel Il Piccolo Castello

Monteriggioni

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

Rp2.355.483 total

includes taxes & fees

15 Nov - 16 Nov

5. Hotel Borgo San Luigi

Monteriggioni

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

Rp2.371.521 total

includes taxes & fees

15 Nov - 16 Nov

A swimming pool with a clear reflection, surrounded by trees and a building with a sloped roof.

6. Relais Castel Bigozzi

Monteriggioni

Rp2.003.885 total

includes taxes & fees

12 Nov - 13 Nov

A pool area with lounge chairs and umbrellas, a view of a hilltop town with historic buildings.

7. Cappuccina Country Resort

San Gimignano

Splash into Tuscan bliss at this seasonal pool oasis, complete with poolside bar and scenic rooftop views.

Rp3.866.858 total

includes taxes & fees

13 Nov - 14 Nov

A rectangular pool with lounge chairs and umbrellas, surrounded by trees and a view of distant hills.

8. Villa Nencini

Volterra

Seasonal outdoor pool sanctuary with rooftop terrace views offers a tranquil Tuscan retreat in garden surroundings.

Rp1.489.701 total

includes taxes & fees

19 Nov - 20 Nov

A poolside area with lounge chairs and umbrellas, surrounded by stone tiles and trees.

9. Agriturismo Nerbona

Colle di Val d'Elsa

Tuscany's idyllic seasonal outdoor pool offers sun-soaked relaxation among garden views at this charming farm stay retreat.

Rp3.315.468 total

includes taxes & fees

13 Nov - 14 Nov

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with tall trees in the background.

10. Torraccia di Chiusi

San Gimignano

Splash into rustic charm at this Tuscan retreat with seasonal outdoor pool and hilltop views.

Rp3.368.723 total

includes taxes & fees

16 Nov - 17 Nov

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Choose what matters most at hotels with a pool in Montecastelli

Breakfast included

4 stars

Top Montecastelli Hotel Reviews

Torraccia di Chiusi

San Gimignano

10/10 Excellent

After the drive from Pisa airport, the drive up the 4km track led to a most stunning property. We were immediately welcomed by Stefano (and two cold beers!) and the hospitality continued throughout our stay. The five course Tuscan dinner every evening was worth every cent and how amazing were the team in making sure everything was perfect?! The pool was beautiful with stunning views. Truly an incredible location, breakfast, hosts, staff and home-grown, home-made food and drink. Thank you for...

David

A pool area with lounge chairs and umbrellas, surrounded by greenery and buildings.

Hotel Sovestro

San Gimignano

10/10 Excellent

Hotel Sovestro is a friendly, relaxing place with two swimming pools and an indoor and outdoor breakfast area. Linked to the hotel next door is a lovely restaurant. Our stay was perfect at the hotel. The room was spacious and comfortable with a balcony overlooking the Tuscan countryside. The continental breakfast choice is outstanding and the entire hotel is kept very clean and up together. The walk to San Gimignano was a little further than we anticipated but it can be done in a leisurely 30...

Ruth

A stone building with a swimming pool, outdoor seating, and a waterfall feature.

Tenuta Sovestro - Agriturismo e Winery

San Gimignano

10/10 Excellent

Aileen

A balcony with a view of the sunset, a pool, and a metal container with rocks.

Hotel Torciano Vecchio Asilo

San Gimignano

10/10 Excellent

Fantastic hospitality and service. We booked a one night stay (very late as we were at the superb vineyard down the road and arrived after just 2 hours later) but this was no trouble. We were greeted first by the owner's lovely daughter and then the owner who made us feel welcome immediately. The room was basic but very clean and pretty. A nice touch to be able to buy beer, wine, snacks etc. out of hours from the large 'minibar' fridge in the hall ir local chianti in the room. The breakfast was...

Gary

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

Villa San Lucchese

Poggibonsi

10/10 Excellent

Anonymous traveller

A swimming pool with lounge chairs and a view of a hill with buildings.

Agriturismo Il Casolare di Bucciano

San Gimignano

10/10 Excellent

Anish

Relais Castel Bigozzi

Monteriggioni

10/10 Excellent

Bob

A pool area with a view of the countryside, surrounded by a wooden deck and outdoor furniture.

Poderi Arcangelo Glamping

San Gimignano

10/10 Excellent

Amazing place to stay. Simple and unpretentious. Clean, comfortable and modern. Great views (room and bar terrace) and nice staff. Glamping pods are separate from the main house and feel very private and secluded. Beautiful setting overlooking the hills and vineyards. Room (Olive suite) had a coffee machine and mini fridge with complimentary drinks/snacks. Large outdoor wrap-around terrace which got sun all day and late into the evening. Views overlooking the vineyards and rolling hills....

Craig

Frequently Asked Questions

What are some accommodation options with pools in Montecastelli?

Hotel Italia: Offers a snack bar/deli, 3 outdoor swimming pools and free self parking. Poderi Arcangelo: Provides a snack bar/deli, a seasonal outdoor pool and free self parking. Hotel Casolare Le Terre Rosse: Hotel located near Piazza del Campo. Features a children's pool, a seasonal outdoor pool and free self parking. Villa Ermellina Siena, a Tribute Portfolio Hotel: Offers a rooftop terrace, 2 outdoor swimming pools and a snack bar/deli. Hotel Sovestro: Features a children's pool, a seasonal outdoor pool and a rooftop terrace.

What is there to see and do in Montecastelli?

Make a point to visit attractions such as Sentierelsa Trail 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.

Search Hotels with Pool in Montecastelli

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Treat yourself

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Check prices for these dates

Our top choices for Montecastelli hotels with a pool

1. Castello di Casole, A Belmond Hotel, Tuscany

2. Villa Sabolini

3. Tenuta Decimo

4. Hotel Il Piccolo Castello

5. Hotel Borgo San Luigi

6. Relais Castel Bigozzi

7. Cappuccina Country Resort

8. Villa Nencini

9. Agriturismo Nerbona

10. Torraccia di Chiusi

Choose what matters most at hotels with a pool in Montecastelli

Top Montecastelli Hotel Reviews

Torraccia di Chiusi

10/10 Excellent

Frequently Asked Questions

What are some accommodation options with pools in Montecastelli?

What is there to see and do in Montecastelli?

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