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
Aug 22 - Aug 23
Tomorrow
Aug 23 - Aug 24
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Our top choices for Pienza hotels with a pool

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 buffet with various desserts and pastries, a painting on the wall, and wooden paneling.

1. 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.
$199 nightly
$226 total
Aug 23 - Aug 24
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 tiled roof, surrounded by a grassy area and flowering plants.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.
A stone building with a gravel pathway leading to the entrance.

2. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
  • Luxurious Tuscan retreat with outdoor pool, onsite winery, and cycling adventures amid rolling hills near Pienza Cathedral.
$187 nightly
$211 total
Sep 21 - Sep 22
Total with taxes and fees
Agriturismo Il Macchione
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and greenery.
An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.
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.

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.
$245 nightly
$274 total
Aug 24 - Aug 25
Total with taxes and fees
Tenuta Santo Pietro
A rectangular swimming pool with clear water, surrounded by a brick patio.
A villa with a tower, a swimming pool, and a well-maintained garden.
A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.
A sculpture in a grassy area with dense trees in the background.

4. Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
  • Seasonal mountain poolside paradise awaits at Hotel Rutiliano's relaxation sanctuary.
$203 nightly
$228 total
Aug 28 - Aug 29
Total with taxes and fees
Hotel Rutiliano Centro Benessere
A pool with lounge chairs, a stone wall, and a view of rolling hills.
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.
A rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.

5. Podere Spedalone

Podere Spedalone
Pienza
  • Relax in the Tuscan countryside at this farm stay with a seasonal outdoor pool.
$153 nightly
$173 total
Aug 23 - Aug 24
Total with taxes and fees
Podere Spedalone
A swimming pool with sun loungers and umbrellas, surrounded by lush greenery and a house with a tiled roof.
A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.
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.

6. L'Olmo

L'Olmo
Pienza
  • Scenic Tuscan countryside poolside retreat offers loungers, umbrellas, and mountain biking access.
$736 nightly
$814 total
Aug 29 - Aug 30
Total with taxes and fees
L'Olmo
A swimming pool with a view of a hilly landscape, surrounded by trees and grass.
A dining area with brick walls, large windows, and a rustic stone ceiling. Tables are set with white tablecloths and candles.
A restaurant with brick arches, white tablecloths, and floral centerpieces.
A large estate with multiple buildings, a swimming pool, and expansive green fields.

7. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
  • Splashy seasonal pool moments at this lakeside farm stay with Italian restaurant and garden oasis.
$165 nightly
$185 total
Sep 22 - Sep 23
Total with taxes and fees
Borgo Sant'Ambrogio Resort
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 balcony with an arched view of a rural landscape, including fields and distant hills.
An arched doorway leading to a room with a large window, stone walls, and a potted plant outside.

8. Locanda Vesuna

Locanda Vesuna
Trequanda
$230 nightly
$257 total
Sep 17 - Sep 18
Total with taxes and fees
Locanda Vesuna
A cave-like interior with a central hot spring, rocky formations, and a staircase leading to a higher level.
A glass-enclosed pool area with multiple levels and seating, surrounded by trees and stone walls.
An indoor rock formation with a hot tub and a waterfall feature.
A bathroom with a glass shower enclosure, a white sink, and a mirror.

9. Wellness Center Casanova Hotel e SPA

Wellness Center Casanova Hotel e SPA
San Quirico d'Orcia
  • Tuscan getaway elevates relaxation with a seasonal outdoor pool, tennis court, and spa services for a refreshing retreat.
$201 nightly
$226 total
Sep 9 - Sep 10
Total with taxes and fees
Wellness Center Casanova Hotel e SPA
An indoor swimming pool with a central circular platform, large columns, and a stone wall.
A multi-story hotel with a well-lit facade, a parking area with several cars, and a sign indicating the hotel's name.
A hotel room with a bed, a desk, a chair, and a view of the outdoors.
A view from a window overlooking a landscape with a small building and hills.

10. Albergo San Biagio

Albergo San Biagio
Montepulciano
  • Elegant indoor pool sanctuary with a dedicated kids' pool creates splashy vacation magic for all ages.
$62 nightly
$73 total
Sep 21 - Sep 22
Total with taxes and fees
Albergo San Biagio
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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 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 swimming pool with a water feature, surrounded by greenery and a table with chairs.

Hotel San Gregorio

Hotel San Gregorio
Pienza
$199 nightly
$226 total
Aug 23 - Aug 24
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 tiled roof, surrounded by a grassy area and flowering plants.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.
A stone building with a gravel pathway leading to the entrance.

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
$187 nightly
$211 total
Sep 21 - Sep 22
Total with taxes and fees
Agriturismo Il Macchione
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.
A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
$245 nightly
$274 total
Aug 24 - Aug 25
Total with taxes and fees
Tenuta Santo Pietro
A modern interior with a stone wall, wooden paneling, and a television.
A villa with a tower, a swimming pool, and a well-maintained garden.
A modern bathroom with a glass partition, two chrome fixtures, and warm lighting.
A rectangular swimming pool with clear water, surrounded by a brick patio.

Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
$203 nightly
$228 total
Aug 28 - Aug 29
Total with taxes and fees
Hotel Rutiliano Centro Benessere
An outdoor dining setup with various dishes on rustic wooden tables, set against a scenic backdrop of rolling hills and a sunset.
A large outdoor swimming pool with multiple sections, surrounded by lounge chairs and a modern building with a unique roof structure.
A restaurant with a rustic interior, featuring exposed brick arches, wooden beams, and a bar area in the background.
A rustic stone building with a tower, surrounded by lush greenery and a vegetable garden.

Podere Spedalone

Podere Spedalone
Pienza
$153 nightly
$173 total
Aug 23 - Aug 24
Total with taxes and fees
Podere Spedalone
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 bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.
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.

L'Olmo

L'Olmo
Pienza
$736 nightly
$814 total
Aug 29 - Aug 30
Total with taxes and fees
L'Olmo
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

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Yan Bo 1-night trip
Posted 4 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Nice staff great location wonderful breakfast"
shane 1-night trip
Posted 4 days ago
Hotel Corsignano
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

10/10 Excellent
"Beautiful property and location."
Gary 1-night trip
Posted 8 days ago
Il Falconiere - Relais e Chateaux
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."
Amy 2-night trip
Posted 8 days ago
Castello di Velona Resort Thermal SPA & Winery
Agriturismo La Sovana

Agriturismo La Sovana

10/10 Excellent
"Beautiful stay here. Restaurant was fantastic and they prepared special dishes to meet our vegetarian needs. Buffet breakfast with fresh cappuccinos was wonderful. Room was impeccably clean with daily cleaning service. This was our second time here and we are hoping to return to this authentic Tuscany resort. You will likely not find a better place to stay at in Tuscany."
Karen 4-night trip
Posted 13 days ago
Agriturismo La Sovana
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Best hotel ever."
Ray 2-night trip
Posted 1 month ago
Castiglion del Bosco, A Rosewood Hotel
Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent
"Beautiful room and property. Location was very convenient to many small hill towns. Staff were wonderful, especially Bertina. Will be back!"
Judy 7-night trip
Posted 3 months ago
Tenuta Santo Pietro
Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent
"The hotel was beautiful maintained and a very convenient location. We stayed in a newly renovated room which was quite modern and clean with excellent spaces for clothes and toiletries which I appreciated! Our room didn’t have a view, it looked onto another building which I was a bit disappointed about. The breakfast was average, too many sweet dessert choices for my taste, but there were eggs and and a nice yogurt bar. The pool area looks nicer in the pictures than it does in person but the pool itself was nice and refreshing. They could have furnished the pool area nicer considering the area we were in! The staff were helpful and friendly, hotel was very convenient with lots of parking and it was very clean."
Traci 2-night trip
Posted 3 months 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 $70 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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