A historic square with a prominent tower and statues.

Hotels with Swimming Pools in Pienza

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Check availability on Pienza Hotels with Swimming Pools

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 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.

1. Relais Cloister Pienza

Relais Cloister Pienza
Pienza
S$189
includes taxes & fees
25 Oct - 26 Oct
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.
S$191
includes taxes & fees
8 Nov - 9 Nov
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.

3. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
  • Luxurious Tuscan retreat with outdoor pool, on-site winery, and cycling adventures amid rolling hills near Pienza Cathedral.
S$191
includes taxes & fees
5 Nov - 6 Nov
Agriturismo Il Macchione
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.
A building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

4. Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
  • Seasonal outdoor pool nestled among the vineyards welcomes summer travellers with loungers, umbrellas, and poolside drinks service.
S$342
includes taxes & fees
12 Oct - 13 Oct
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 dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.
A sculpture in a grassy area with dense trees in the background.

5. Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
  • Seasonal mountain poolside paradise awaits at Hotel Rutiliano's relaxation sanctuary.
S$280
includes taxes & fees
15 Oct - 16 Oct
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.
S$222
includes taxes & fees
30 Oct - 31 Oct
Podere Spedalone
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 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.

7. L'Olmo

L'Olmo
Pienza
  • Scenic Tuscan countryside poolside retreat offers loungers, umbrellas, and mountain biking access.
S$637
includes taxes & fees
2 Nov - 3 Nov
L'Olmo
A serene outdoor pool area with a view of rolling hills and a sunset sky.
Terrace/patio
A bedroom with a bed, a chair, a desk, and a window with curtains.
A stone house with a tiled roof, a patio with a lounge chair, and a view of rolling hills in the background.

8. Relais Val d'Orcia

Relais Val d'Orcia
Pienza
S$344
includes taxes & fees
25 Oct - 26 Oct
Relais Val d'Orcia
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 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.

9. Locanda Vesuna

Locanda Vesuna
Trequanda
S$182
includes taxes & fees
12 Oct - 13 Oct
Locanda Vesuna
A swimming pool with lounge chairs and umbrellas, a stone building with a tiled roof, and a clear blue sky.
A hotel room with a bed, a sofa, a chair, a small table with a lamp, and a window with a view of a green landscape.
A modern bathroom with a marble shower wall, a large mirror, and a wooden vanity.
A table set with a bottle of wine, two wine glasses, and a vase with flowers.

10. Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
  • Summer seclusion at this Tuscan spa retreat with poolside relaxation and gourmet dining.
S$303
includes taxes & fees
3 Nov - 4 Nov
Poggio Paradiso Resort & Spa
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 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.

Relais Cloister Pienza

Relais Cloister Pienza
Pienza
S$189
includes taxes & fees
25 Oct - 26 Oct
Relais Cloister 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
S$191
includes taxes & fees
8 Nov - 9 Nov
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
S$191
includes taxes & fees
5 Nov - 6 Nov
Agriturismo Il Macchione
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 building with a stone facade, surrounded by trees and shrubs, and illuminated by warm lights.

Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
S$342
includes taxes & fees
12 Oct - 13 Oct
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 living room with a sofa, coffee table, TV, bookshelves, and a decorative lamp.
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.

L'Olmo

L'Olmo
Pienza
S$637
includes taxes & fees
2 Nov - 3 Nov
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
S$222
includes taxes & fees
30 Oct - 31 Oct
Podere Spedalone
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 dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.
A rectangular swimming pool with clear water, surrounded by a brick patio.

Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere
Pienza
S$280
includes taxes & fees
15 Oct - 16 Oct
Hotel Rutiliano Centro Benessere
Terrace/patio
A serene outdoor pool area with a view of rolling hills and a sunset sky.
A bedroom with a bed, a chair, a desk, and a window with curtains.
A stone house with a tiled roof, a patio with a lounge chair, and a view of rolling hills in the background.

Relais Val d'Orcia

Relais Val d'Orcia
Pienza
S$344
includes taxes & fees
25 Oct - 26 Oct
Relais Val d'Orcia
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

Hotel San Gregorio

Hotel San Gregorio

8/10 Good
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"
Julia 2-night trip
Posted 2 days ago
Hotel San Gregorio
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Nice and quiet excellent hospitality"
Mohammed 2-night trip
Posted 4 days ago
Castiglion del Bosco, A Rosewood Hotel
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"
lynda 3-night trip
Posted 5 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Palazzuolo

Palazzuolo

10/10 Excellent
"Excellent room, good location, the staff is very gentle, the breakfast is good"
Nami 2-night trip
Posted 11 days ago
Palazzuolo
Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!"
Julia 5-night trip
Posted 12 days ago
Hotel Certosa Di Maggiano
La Bandita Townhouse

La Bandita Townhouse

10/10 Excellent
"Great 12 room boutique hotel in the heart of Pienza."
Robert 1-night trip
Posted 12 days ago
La Bandita Townhouse
Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"Personal, muy amable y educado, muy cálida, recepción, lindo hotel. Lo aconsejo para quienes quieran visitar la toscana y sobretodo Montepulciano."
Julio 1-night trip
Posted 13 days ago
Hotel Villa Ricci
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 13 days ago
Castello di Velona Resort Thermal SPA & Winery

Frequently asked questions

What's it like visiting Pienza?
If spending time by the pool is your idea of the perfect getaway, you may want to explore luxurious Pienza, which has 8 places to stay with pools. While you're visiting, you can explore sights such as Palazzo Piccolomini and Historic Centre of Pienza, and then relax and unwind poolside at one of the accommodation options 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 televisions. 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 sunloungers, a pool and complimentary wireless Internet access.
How many hotels with pools will I find 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 such as Historic Centre of Pienza and Art Studio di Adelina Quadri. During your stay, visit 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 with an outdoor swimming pool if you plan to visit Pienza in the warmest months of August, July or June, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is 5°C.

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