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

Hotels with Swimming Pool in Casole d'Elsa, Tuscany

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Casole d'Elsa Hotels with Swimming Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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

A hotel with a pool, outdoor seating, and a mountainous backdrop.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.
An outdoor patio with a stone wall, wooden table, chairs, potted plants, and a stone fireplace.

1. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
  • A dreamy Tuscan poolside escape where luxury meets Italian countryside charm.
P78,089
P86,040 total
includes taxes & fees
Nov 1 - Nov 2
Castello di Casole, A Belmond Hotel, Tuscany
A clear blue pool with a view of distant mountains and trees.
A modern bathroom with a marble vanity, a glass shower enclosure, and a large mirror.
A dining area with tables set for breakfast, overlooking a scenic landscape.
A table set for dining with a view of the countryside.

2. Relax Hotel Acquaviva

Relax Hotel Acquaviva
Il Merlo
P5,225
P6,315 total
includes taxes & fees
Oct 8 - Oct 9
Relax Hotel Acquaviva
A swimming pool with tiled flooring, lounge chairs, and umbrellas.
A cozy living room with a wooden dining table, a sofa, and a fireplace.
A stone building with a paved courtyard, surrounded by grass and a brick pathway.
A stone building with a tiled roof, a brick pathway, and a small grassy area.

3. Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
P12,901
P14,333 total
includes taxes & fees
Oct 3 - Oct 4
Le Mascie Country House
A swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.
A dining area with wooden tables and chairs, large windows offering a view of a forested landscape.
A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.
A well-lit outdoor bar area with a wooden structure, surrounded by lush greenery and stone pathways.

4. Villa Sabolini

Villa Sabolini
Colle di Val d'Elsa
  • Sunshine dances across the tranquil outdoor pool at this historic Tuscan villa.
P5,535
P6,372 total
includes taxes & fees
Nov 1 - Nov 2
Villa Sabolini
Pool
A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
An outdoor patio with stone flooring, a table with chairs, and potted plants.
Breakfast meal

5. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
  • Take a dip in crystal waters as Tuscan countryside surrounds the seasonal pool.
P7,535
P8,786 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Borgo San Luigi
A wooden pathway leading to a pool area with a gazebo and potted plants.
A courtyard with a statue, stone walls, and a reception sign.
A narrow cobblestone street flanked by stone buildings with arched windows and a central potted plant.
An outdoor dining area with tables and chairs, surrounded by trees and a stone wall.

6. Relais Della Rovere

Relais Della Rovere
Colle di Val d'Elsa
  • Tuscan poolside retreat offers seasonal dips with loungers and umbrellas under the Italian sun.
P8,259
P9,369 total
includes taxes & fees
Oct 30 - Oct 31
Relais Della Rovere
A dining table with a view of a pool and landscaped garden.
A room with a fireplace, a table with a tray of food, and two lamps on either side of the fireplace.
A table set for breakfast with a scenic view of hills and trees.
A poolside area with red umbrellas and lounge chairs, a building with balconies, and a clear blue sky.

7. Relais Santa Chiara Hotel by Double Hospitality

Relais Santa Chiara Hotel by Double Hospitality
San Gimignano
  • Splash into Tuscan serenity with a seasonal pool oasis that serves chilled drinks poolside.
P6,613
P7,771 total
includes taxes & fees
Oct 20 - Oct 21
Relais Santa Chiara Hotel by Double Hospitality
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A neatly made breakfast tray on a bed with a tray of bread, fruit, juice, and tea, in a room with a bed, curtains, and a painting on the wall.
A covered outdoor dining area with tables and chairs, a pool, and a garden in the background.
A bathroom with a glass-enclosed shower, a white sink, and a large mirror with wall sconces.

8. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
Monteriggioni
  • Seasonal outdoor pool paradise nestled in rural Italy, where sunny loungers and poolside drinks await amidst Tuscan adventures.
P7,083
P8,289 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Il Piccolo Castello
A swimming pool with clear water, surrounded by stone walls and lush greenery, overlooking a scenic landscape.
A covered outdoor dining area with a table set for four, overlooking a scenic landscape with hills and a body of water.
A stone-walled room with a bench and a small shelf.
A stone building with a tiled roof, a gravel path leading to a wooden archway, and a sign reading "LA FONTE".

9. Borgo Pignano Volterra Tuscany

Borgo Pignano Volterra Tuscany
Volterra
  • Serene Tuscan getaway with 2 outdoor pools and children's splash zone, nestled near historic San Gimignano landmarks.
P32,252
P35,832 total
includes taxes & fees
Oct 22 - Oct 23
Borgo Pignano Volterra Tuscany
A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.
A yellow building with stone pillars, multiple windows, and a statue in the garden.
A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.
A room with a sofa, a desk, a bunk bed, and a patterned floor.

10. Villa San Lucchese

Villa San Lucchese
Poggibonsi
  • Sun-drenched poolside retreat with waterslide and children's pool awaits at this Tuscan villa.
P6,588
P7,672 total
includes taxes & fees
Oct 30 - Oct 31
Villa San Lucchese
View all properties

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

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Casole d'Elsa Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"
Carole 5-night trip
Posted 16 hours ago
Castiglion del Bosco, A Rosewood Hotel
Castelfalfi

Castelfalfi

10/10 Excellent
"The true meaning of Perfection. I've never said that about any accommodations"
Larry 4-night trip
Posted 1 day ago
Castelfalfi
Hotel Athena

Hotel Athena

10/10 Excellent
"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."
Michele 2-night trip
Posted 2 days ago
Hotel Athena
Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Absolutely stunning property with amazing staff. Tons of wineries close by and touring thru San Gimignano was fascinating. Definitely 5/5."
Jodie 1-night trip
Posted 2 days ago
Hotel Casolare Le Terre Rosse
Poderi Arcangelo

Poderi Arcangelo

8/10 Good
"We enjoyed our stay. The pool, hotel grounds and location were truly amazing. The food was okay but we enjoyed eating off site more. The farmhouse is very quaint and charming. You can hear others in the farmhouse. It was luxurious in many ways and more basic in other ways. But all together a wonderful stay. I would recommend for sure."
Kathy 5-night trip
Posted 3 days ago
Poderi Arcangelo
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent
"Beautiful hotel that is close to a bus line to get into the city. The views and accommodations make this a wonderful place to stay."
Heather 6-night trip
Posted 6 days ago
Villa Ermellina Siena, a Tribute Portfolio Hotel
Hotel Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 3 weeks ago
Hotel Italia
Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany

10/10 Excellent
"Once in a lifetime trip. The facilities, the staff, the rooms, the views, the activities were all exceptional."
Kelly 2-night trip
Posted 2 months ago
Castello di Casole, A Belmond Hotel, Tuscany

Frequently asked questions

What's it like visiting Casole d'Elsa?
If taking it easy by the pool is your idea of the perfect getaway, you may want to check out quaint Casole d'Elsa, which offers 6 places to stay with pools. During your visit, you can explore sights such as Val di Merse and Terre di Vini, and then relax and unwind poolside at one of the accommodations in Casole d'Elsa that guests like for their pools.
What are some accommodations with pools in Casole d'Elsa?
Castello di Casole, A Belmond Hotel, Tuscany: Features 3 restaurants, an outdoor pool, and a full-service spa. Castelfalfi: Offers 4 restaurants, a seasonal outdoor pool, and a full-service spa. La Certosa di Pontignano: Features a snack bar/deli, 3 outdoor pools, and free self parking. Hotel Athena: Offers a rooftop terrace, an outdoor pool, and a snack bar/deli. NH Siena: Provides 2 restaurants, 2 outdoor pools, and a full-service spa.
How many hotels with pools should I expect to find in Casole d'Elsa?
Expedia has 6 hotels in Casole d'Elsa for your poolside break.
What is there to see and do in Casole d'Elsa?
Make a point to visit attractions like Val di Merse and Terre di Vini. Discover sights such as Archeological and Collegiate Church Museum during your stay.
When is the best time to book a hotel with a pool in Casole d'Elsa?
You may want to consider a place to stay that has an outdoor pool if you will be visiting Casole d'Elsa 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 come to town during the coldest months of January, February, or December when the average temp is 44°F.

Explore a world of travel with Expedia