A historic square with a prominent tower and statues.

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Check availability on Pienza Hotels with a Pool

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Pienza hotels with a pool

A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.
A hotel room with a bed, a shower, a TV, and a cabinet.
A buffet setup with various food items and condiments.
A modern bathroom with a glass-enclosed shower, a white sink, and a toilet.

1. Relais Cloister Pienza

Relais Cloister Pienza
Pienza
￥20,504
￥23,628 total
includes taxes & fees
Oct 29 - Oct 30
Relais Cloister Pienza
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.
A hotel room with a bed, a desk with a computer, a TV, a wardrobe, and a mirror.
A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

2. Hotel San Gregorio

Hotel San Gregorio
Pienza
  • Serene Tuscan retreat boasts a seasonal outdoor pool surrounded by lush gardens, with lounge areas for soaking up the Italian sun.
￥22,803
￥26,159 total
includes taxes & fees
Oct 28 - Oct 29
Hotel San Gregorio
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.
A cozy room with a fireplace, two armchairs, and a table.
A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.
An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

3. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
  • Seasonal outdoor pool nestled among the vineyards welcomes summer travelers with loungers, umbrellas, and poolside drinks service.
￥34,692
￥38,877 total
includes taxes & fees
Oct 30 - Oct 31
Tenuta Santo Pietro
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.
A stone building with a tiled roof, surrounded by a grassy area and flowering plants.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.

4. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
  • Luxurious Tuscan retreat with outdoor pool, onsite winery, and cycling adventures amid rolling hills near Pienza Cathedral.
￥31,134
￥34,964 total
includes taxes & fees
Oct 27 - Oct 28
Agriturismo Il Macchione
A pool with lounge chairs, a stone wall, and a view of rolling hills.
A rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.

5. Podere Spedalone

Podere Spedalone
Pienza
  • Relax in the Tuscan countryside at this farm stay with a seasonal outdoor pool.
￥24,556
￥27,727 total
includes taxes & fees
Oct 30 - Oct 31
Podere Spedalone
A rectangular swimming pool with clear water, surrounded by a brick patio.
A sculpture in a grassy area with dense trees in the background.
A dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.
A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.

6. Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
  • Seasonal mountain poolside paradise awaits at Hotel Rutiliano's relaxation sanctuary.
￥31,155
￥34,986 total
includes taxes & fees
Oct 4 - Oct 5
Hotel Rutiliano Centro Benessere
A large, single-story building with a tiled roof, a covered patio area with outdoor seating, and a well-maintained lawn.
A breakfast buffet with various dishes and a person serving.
A building with a window, a gravel path, and a flower bed with red and pink flowers.
A bathroom with a glass-enclosed shower, a sink with chrome fixtures, and a mirror above the sink.

7. Agriturismo Poggio Tobruk

Agriturismo Poggio Tobruk
Pienza
  • Soak in natural hot springs at a charming farm stay with indoor pool access and poolside bliss.
￥25,198
￥28,434 total
includes taxes & fees
Oct 4 - Oct 5
Agriturismo Poggio Tobruk
A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.
A cozy reading room with a fireplace, bookshelves, and comfortable seating.
A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.
A cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.

8. L'Olmo

L'Olmo
Pienza
  • Scenic Tuscan countryside poolside retreat offers loungers, umbrellas, and mountain biking access.
￥78,759
￥87,351 total
includes taxes & fees
Oct 30 - Oct 31
L'Olmo
Pool
Living area
Dining
Interior

9. Podere Manafiore - historical villa with swimming pool

Podere Manafiore - historical villa with swimming pool
Monticchiello
Podere Manafiore - historical villa with swimming pool
A pool area with lounge chairs and umbrellas, surrounded by a field of lavender.
A stone courtyard with a fountain, outdoor seating, and a view of the countryside.
A stone building with a brick pathway leading to an arched entrance.
An arched doorway leading to a room with a large window, stone walls, and a potted plant outside.

10. Locanda Vesuna

Locanda Vesuna
Trequanda
￥32,545
￥36,336 total
includes taxes & fees
Oct 13 - Oct 14
Locanda Vesuna
View all properties

Choose what matters most at hotels with a pool in Pienza

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in Pienza

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.
A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.
A buffet setup with various food items and condiments.
A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

Relais Cloister Pienza

Relais Cloister Pienza
Pienza
￥20,504
￥23,628 total
includes taxes & fees
Oct 29 - Oct 30
Relais Cloister Pienza
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.
A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.
A hotel room with a bed, a desk with a computer, a TV, a wardrobe, and a mirror.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.

Hotel San Gregorio

Hotel San Gregorio
Pienza
￥22,803
￥26,159 total
includes taxes & fees
Oct 28 - Oct 29
Hotel San Gregorio
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.
A stone building with a tiled roof, surrounded by a grassy area and flowering plants.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
￥31,134
￥34,964 total
includes taxes & fees
Oct 27 - Oct 28
Agriturismo Il Macchione
A modern interior with a stone wall, wooden paneling, and a television.
A rectangular swimming pool with clear water, surrounded by a brick patio.
A dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.
A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.

Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
￥31,155
￥34,986 total
includes taxes & fees
Oct 4 - Oct 5
Hotel Rutiliano Centro Benessere
A cozy room with a fireplace, two armchairs, and a table.
An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.
A cozy room with a pool table, comfortable seating, and a large arched window offering a view of the outdoors.

Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
￥34,692
￥38,877 total
includes taxes & fees
Oct 30 - Oct 31
Tenuta Santo Pietro
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.
A cozy reading room with a fireplace, bookshelves, and comfortable seating.
A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.
A cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.

L'Olmo

L'Olmo
Pienza
￥78,759
￥87,351 total
includes taxes & fees
Oct 30 - Oct 31
L'Olmo
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.
A rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.
A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.

Podere Spedalone

Podere Spedalone
Pienza
￥24,556
￥27,727 total
includes taxes & fees
Oct 30 - Oct 31
Podere Spedalone
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Pienza Hotel Reviews

La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Great 12 room boutique hotel in the heart of Pienza."
Robert 1-night trip
Posted 1 day ago
La Bandita Townhouse
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."
Erick 2-night trip
Posted 2 days ago
Castello di Velona Resort Thermal SPA & Winery
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Everything was perfect the staff the hotel."
steve 1-night trip
Posted 5 days ago
Hotel Corsignano
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-night trip
Posted 9 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Quaint but modern hotel walking distance to all - good breakfast and service in hotel restaurant. Spacious rooms with air conditioning (which gets turned off when staff cleans room - call desk to turn back on), safe, and bathroom with tub- but no shower curtain- took a while to learn how to negotiate using the shower handle. Pool area is restful. Enjoyed our stay"
JANET 3-night trip
Posted 12 days ago
Hotel San Gregorio
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Very warm and friendly service."
Abdel 2-night trip
Posted 2 weeks ago
Castiglion del Bosco, A Rosewood Hotel

Frequently asked questions

What's it like visiting Pienza?
If lounging by a pool is your idea of the perfect getaway, you may want to check out luxurious Pienza, which has 8 places to stay with pools. During your trip, you can explore sights such as Palazzo Piccolomini and Historic Centre of Pienza, and then relax and unwind poolside at one of the accommodations in Pienza that guests like for their pools.
What are some hotels with pools in Pienza?
Hotel San Gregorio: Features complimentary wireless internet access, a seasonal outdoor pool, and Smart TVs. Hotel Corsignano: Provides buffet, an outdoor pool, and free self parking. Agriturismo Il Macchione: Features buffet, a seasonal outdoor pool, and free self parking. Tenuta Santo Pietro: Offers buffet, a seasonal outdoor pool, and free self parking. Agriturismo Poggio Tobruk: Provides sun loungers, a pool, and complimentary wireless internet access.
How many hotels with pools are there in Pienza?
Expedia has 8 hotels in Pienza for your poolside break.
What is there to see and do in Pienza?
Make a point to visit attractions like Historic Centre of Pienza and Art Studio di Adelina Quadri. During your stay, check out sights such as Palazzo Piccolomini, Pienza Cathedral, and Val di Chiana.
When is the best time to book a hotel with a pool in Pienza?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Pienza in the warmest months of August, July, or June when the average temp is 69°F. Lodging offering 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 temperature is 42°F.

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