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
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Pienza hotels with a pool

A historic town with a prominent church, a courtyard with a swimming pool, and terraced buildings.
A hotel room with a bed, a desk with a lamp, a television, and a window with curtains.
A room with a red and beige checkered sofa, a matching armchair, a framed picture on the wall, and a window with wooden shutters.
A bathroom with a bathtub, a toilet, and a sink.

1. Relais Cloister Pienza

Relais Cloister Pienza
Pienza
$131 nightly
$151 total
Oct 7 - Oct 8
Total with taxes and fees
Relais Cloister Pienza
A swimming pool with a water feature, surrounded by greenery and a table with chairs.
A modern bathroom with two sinks, a shower, and a toilet.
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.
$199 nightly
$225 total
Oct 6 - Oct 7
Total with taxes and fees
Hotel San Gregorio
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.
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.

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.
$210 nightly
$236 total
Oct 24 - Oct 25
Total with taxes and fees
Tenuta Santo Pietro
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 fire pit with burning logs, surrounded by stone blocks and a metal grill.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

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.
$217 nightly
$243 total
Oct 15 - Oct 16
Total with taxes and fees
Agriturismo Il Macchione
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 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.

5. Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
  • Seasonal mountain poolside paradise awaits at Hotel Rutiliano's relaxation sanctuary.
$199 nightly
$224 total
Sep 28 - Sep 29
Total with taxes and fees
Hotel Rutiliano Centro Benessere
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.

6. Podere Spedalone

Podere Spedalone
Pienza
  • Relax in the Tuscan countryside at this farm stay with a seasonal outdoor pool.
$169 nightly
$191 total
Oct 13 - Oct 14
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 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 cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.

7. L'Olmo

L'Olmo
Pienza
  • Scenic Tuscan countryside poolside retreat offers loungers, umbrellas, and mountain biking access.
$721 nightly
$798 total
Oct 18 - Oct 19
Total with taxes and fees
L'Olmo

8. 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 balcony with an arched view of a rural landscape, including fields and distant hills.
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.

9. Locanda Vesuna

Locanda Vesuna
Trequanda
$152 nightly
$170 total
Sep 28 - Sep 29
Total with taxes and fees
Locanda Vesuna
A clear swimming pool with lounge chairs and a pergola.
A bathroom with a glass shower enclosure, a sink with a mirror, and a towel rack.
A breakfast setup with a variety of food items and a coffee machine.
A bedroom with a bed, bedside table with a lamp, a chair, and a radiator.

10. AgriHotel Villa Ambra

AgriHotel Villa Ambra
Montepulciano
  • Sip and swim through Tuscan vineyard paradise at this wine-connected hotel with 24-hour pool access.
$73 nightly
$85 total
Oct 22 - Oct 23
Total with taxes and fees
AgriHotel Villa Ambra
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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 building with a symmetrical facade, a central entrance, and a fountain in the courtyard.
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
$199 nightly
$225 total
Oct 6 - Oct 7
Total with taxes and fees
Hotel San Gregorio
A hotel room with a bed, a desk, a chair, and a television.
A room with a single bed, two framed pictures on the wall, and a thermostat.
A buffet setup with various food items and utensils.
A historic town with a prominent church, a courtyard with a swimming pool, and terraced buildings.

Relais Cloister Pienza

Relais Cloister Pienza
Pienza
$131 nightly
$151 total
Oct 7 - Oct 8
Total with taxes and fees
Relais Cloister Pienza
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 fire pit with burning logs, surrounded by stone blocks and a metal grill.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
$217 nightly
$243 total
Oct 15 - Oct 16
Total with taxes and fees
Agriturismo Il Macchione
A cozy room with a fireplace, two armchairs, and a table.
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.
A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
$210 nightly
$236 total
Oct 24 - Oct 25
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 reading room with a fireplace, bookshelves, and comfortable seating.
A cozy living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.

L'Olmo

L'Olmo
Pienza
$721 nightly
$798 total
Oct 18 - Oct 19
Total with taxes and fees
L'Olmo
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 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.

Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
$199 nightly
$224 total
Sep 28 - Sep 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 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
$169 nightly
$191 total
Oct 13 - Oct 14
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

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"Loved our stay at the hotel - super relaxing and great for our honeymoon. The staff were so kind and really helpful"
Melanie 2-night trip
Posted 9 hours ago
Castello di Velona Resort Thermal SPA & Winery
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 3 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 6 days ago
Hotel San Gregorio
Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent
"Beautiful place to stay halfway between Pienza and Montepulciano. The food was some of the best we had during our entire time in Italy and we loved spending our afternoon by the pool with a drink."
Jenny 2-night trip
Posted 8 days ago
Tenuta Santo Pietro
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 10 days ago
Castiglion del Bosco, A Rosewood Hotel
La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Fantastic venue! Loved Pienza! The Inn was beautiful and the staff extremely friendly and welcoming. We would love to go back"
Ross 1-night trip
Posted 3 weeks ago
La Bandita Townhouse

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 $85 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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