A historic square with a prominent tower and statues.

Find Hotels with a Pool in Pienza

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Check availability on Pienza Hotels with a 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 Pienza hotels with a pool

A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.
A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.
A modern bathroom with a glass-enclosed shower, a white sink, and a toilet.
A hotel room with a bed, a shower, a TV, and a cabinet.

1. Relais Cloister Pienza

Relais Cloister Pienza
Pienza
$130 nightly
$150 total
Oct 15 - Oct 16
Total with taxes and fees
Relais Cloister Pienza
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.
A modern bathroom with two sinks, a shower, and a toilet.
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

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.
$144 nightly
$166 total
Oct 28 - Oct 29
Total with taxes and fees
Hotel San Gregorio
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A stone building with a gravel pathway leading to the entrance.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.

3. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
  • Luxurious Tuscan retreat with outdoor pool, onsite winery, and cycling adventures amid rolling hills near Pienza Cathedral.
$195 nightly
$219 total
Oct 27 - Oct 28
Total with taxes and fees
Agriturismo Il Macchione
A pool with lounge chairs, a stone wall, and a view of rolling hills.
A rustic villa with traditional architecture, surrounded by olive groves and a mountainous backdrop.
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.

4. Podere Spedalone

Podere Spedalone
Pienza
  • Relax in the Tuscan countryside at this farm stay with a seasonal outdoor pool.
$155 nightly
$176 total
Oct 30 - Oct 31
Total with taxes and fees
Podere Spedalone
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 building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.
An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

5. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
  • Seasonal outdoor pool nestled among the vineyards welcomes summer travelers with loungers, umbrellas, and poolside drinks service.
$215 nightly
$241 total
Oct 30 - Oct 31
Total with taxes and fees
Tenuta Santo Pietro
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 two-story building with a flat roof and a small balcony on the second floor.
A bathroom with a glass-enclosed shower, a sink with chrome fixtures, and a mirror above the sink.

6. Agriturismo Poggio Tobruk

Agriturismo Poggio Tobruk
Pienza
  • Soak in natural hot springs at a charming farm stay with indoor pool access and poolside bliss.
$148 nightly
$168 total
Oct 4 - Oct 5
Total with taxes and fees
Agriturismo Poggio Tobruk
A rectangular swimming pool with clear water, surrounded by a brick patio.
A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.
A villa with a tower, a swimming pool, and a well-maintained garden.
A sculpture in a grassy area with dense trees in the background.

7. Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
  • Seasonal mountain poolside paradise awaits at Hotel Rutiliano's relaxation sanctuary.
$197 nightly
$222 total
Oct 4 - Oct 5
Total with taxes and fees
Hotel Rutiliano Centro Benessere
A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.
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 living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.
A cozy reading room with a fireplace, bookshelves, and comfortable seating.

8. L'Olmo

L'Olmo
Pienza
  • Scenic Tuscan countryside poolside retreat offers loungers, umbrellas, and mountain biking access.
$499 nightly
$553 total
Oct 30 - Oct 31
Total with taxes and fees
L'Olmo
Pool
Living area
Dining
Outdoor dining

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 building with a brick pathway leading to an arched entrance.
A stone courtyard with a fountain, outdoor seating, and a view of the countryside.
An arched doorway leading to a room with a large window, stone walls, and a potted plant outside.

10. Locanda Vesuna

Locanda Vesuna
Trequanda
$196 nightly
$219 total
Oct 13 - Oct 14
Total with taxes and fees
Locanda Vesuna
View all properties

Choose what matters most at hotels with a pool in Pienza

Breakfast included
4 stars
5 stars
Spa
Hot tub

Hotels with pools and free breakfast in Pienza

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.
A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.
A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.
A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

Relais Cloister Pienza

Relais Cloister Pienza
Pienza
$130 nightly
$150 total
Oct 15 - Oct 16
Total with taxes and fees
Relais Cloister Pienza
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
A building with a symmetrical facade, a central entrance, and a fountain in the courtyard.
A buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

Hotel San Gregorio

Hotel San Gregorio
Pienza
$144 nightly
$166 total
Oct 28 - Oct 29
Total with taxes and fees
Hotel San Gregorio
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A stone building with a gravel pathway leading to the entrance.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.
A fire pit with burning logs, surrounded by stone blocks and a metal grill.

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
$195 nightly
$219 total
Oct 27 - Oct 28
Total with taxes and fees
Agriturismo Il Macchione
A modern interior with a stone wall, wooden paneling, and a television.
A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.
A villa with a tower, a swimming pool, and a well-maintained garden.
A rectangular swimming pool with clear water, surrounded by a brick patio.

Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
$197 nightly
$222 total
Oct 4 - Oct 5
Total with taxes and fees
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 building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.
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
$215 nightly
$241 total
Oct 30 - Oct 31
Total with taxes and fees
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 swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.
A cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.
A cozy reading room with a fireplace, bookshelves, and comfortable seating.

L'Olmo

L'Olmo
Pienza
$499 nightly
$553 total
Oct 30 - Oct 31
Total with taxes and fees
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 villa with traditional architecture, surrounded by olive groves and a mountainous backdrop.
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.

Podere Spedalone

Podere Spedalone
Pienza
$155 nightly
$176 total
Oct 30 - Oct 31
Total with taxes and fees
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

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 6 hours ago
Castiglion del Bosco, A Rosewood Hotel
La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Great 12 room boutique hotel in the heart of Pienza."
Robert 1-night trip
Posted 3 days 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 4 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 6 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 10 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 13 days ago
Hotel San Gregorio

Frequently asked questions

How much does a hotel with outdoor pool in Pienza cost?
Enjoy staying in a hotel in Pienza with an outdoor pool. You can find a great deal from $150 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Pienza that have private outdoor pools?
If you're searching for a serene getaway in Pienza, the "House with private pool with beautiful view Val d'Orcia" could be your great choice. This stunning property boasts a private outdoor pool, allowing you to soak in the sun while enjoying breathtaking views of the Val d'Orcia landscape. With a remarkable review rating of 9.8, it's clear that guests are captivated by the beauty and tranquility this house offers.Beyond the pool, this charming accommodation features a well-equipped kitchen, making it convenient for families to prepare meals together. Outdoor enthusiasts will appreciate nearby mountain biking opportunities and the secure yard, great for children to play in. The deck and patio areas provide ample space for relaxation, ensuring that your stay is both comfortable and enjoyable.
What are some of the best Pienza hotels with outdoor pools and scenic views?
One exceptional option for travellers seeking a hotel with an outdoor pool and stunning views in Pienza is the "House with Private Pool with Beautiful View Val d'Orcia." Rated an impressive 9.8 by guests, this charming property offers not only a beautiful pool but also breathtaking vistas of the Val d'Orcia landscape.Imagine lounging by the pool while soaking in the scenic beauty that surrounds you, or perhaps enjoying a meal on the deck or patio, where the views are as delightful as the food. The house features a fully equipped kitchen, great for families who appreciate the convenience of preparing their meals. Additionally, for those who love adventure, nearby mountain biking trails offer an exciting way to explore the area's natural beauty.
Is it cheaper to book flights and a Pienza hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Pienza for you.

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