Find Hotels with a Pool in Pienza

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Pienza Hotels with a Pool

Top Pienza Hotels with a Pool

Outdoor pool
Agriturismo Il Macchione

Agriturismo Il Macchione

Pienza
  • Outdoor pool
9.6 out of 10, Exceptional, (55)
Poolside relaxation awaits at this Tuscan haven, where guests can swim surrounded by countryside views before exploring nearby trails on rented bicycles. Fresh, delicious breakfasts fuel days of horseback riding and winery experiences.
$159 nightly
The price is $180
Nov 26 - Nov 27
Total with taxes and fees
Agriturismo Il Macchione
Interior
Hotel Rutiliano Centro Benessere

Hotel Rutiliano Centro Benessere

3.0 star property
Pienza
  • Hot tub
8.6 out of 10, Excellent, (7)
Spa-goers relish the Rutiliano Wellness Center's facials, body scrubs, and massages before floating in the seasonal outdoor pool. Mountain adventures await nearby with hiking trails accessible from this tranquil Italian retreat featuring a sauna and steam room.
Hotel Rutiliano Centro Benessere
Seasonal outdoor pool
Podere Spedalone

Podere Spedalone

1.0 star property
Pienza
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.4 out of 10, Exceptional, (42)
Sparkling waters invite poolside relaxation from May through October at this authentic Tuscan retreat. Beyond swimming, guests savor delicious local cuisine at La Pecora Bianca restaurant, explore nearby hiking trails, or arrange bicycle rentals for countryside adventures.
$181 nightly
The price is $204
Dec 9 - Dec 10
Total with taxes and fees
Podere Spedalone
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Hotel San Gregorio

Hotel San Gregorio

3.0 star property
Pienza
  • Pool loungers
9.4 out of 10, Exceptional, (132)
Refreshing dips await at the seasonal outdoor pool, complete with sun loungers and umbrellas for perfect relaxation. Beyond swimming, this Tuscan-style hotel offers mountain biking trails, bicycle rentals, and a restaurant serving local cuisine.
$137 nightly
The price is $158
Nov 18 - Nov 19
Total with taxes and fees
Hotel San Gregorio
Game room
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

5.0 star property
Trequanda
  • Pool loungers
9.8 out of 10, Exceptional, (94)
Poolside relaxation awaits with comfortable sun loungers and umbrellas from April to November. Bicycle rentals invite exploration of nearby hiking trails while the restaurant serves delicious Italian cuisine crafted from fresh, organic local ingredients.
$141 nightly
The price is $159
Nov 14 - Nov 15
Total with taxes and fees
Borgo Sant'Ambrogio Resort
Outdoor pool
Agriturismo Le Casaline

Agriturismo Le Casaline

4.0 star property
Seggiano
  • Outdoor pool
  • Children's pool
9.0 out of 10, Wonderful, (8)
$109 nightly
The price is $120
Dec 10 - Dec 11
Total with taxes and fees
Agriturismo Le Casaline
Seasonal outdoor pool
The Monteleone

The Monteleone

Monteleone d'Orvieto
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
10.0 out of 10, Exceptional, (5)
$94 nightly
The price is $103
Nov 11 - Nov 12
Total with taxes and fees
The Monteleone
Outdoor pool, pool umbrellas, sun loungers
Abbadia Sicille Relais

Abbadia Sicille Relais

4.0 star property
Trequanda
  • Outdoor pool
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (163)
Luxurious poolside moments define this upscale residence, complemented by a soothing hot tub for evening relaxation. After swimming, savor delicious dinner at the on-site Fondo restaurant while enjoying garden and terrace views.
$75 nightly
The price is $87
Nov 11 - Nov 12
Total with taxes and fees
Abbadia Sicille Relais
Seasonal outdoor pool, sun loungers
Podere Pietreta

Podere Pietreta

Radicofani
  • Pool loungers
8.8 out of 10, Excellent, (15)
Swimming bliss awaits at this rustic farm stay's seasonal outdoor pool, complete with sun loungers and a dedicated children's pool. Cyclists will appreciate bike rentals while families enjoy the playground and picnic area amid the scenic countryside.
$72 nightly
The price is $84
Nov 11 - Nov 12
Total with taxes and fees
Podere Pietreta
Seasonal outdoor pool, open 9:30 AM to 7:00 PM, pool umbrellas
SI Montalcino Hotel

SI Montalcino Hotel

3.0 star property
Montalcino
  • Pool loungers
9.2 out of 10, Wonderful, (376)
Poolside bliss defines summer stays at this Italian hotel, where loungers await under umbrellas from May through September. Mountain biking adventures and Brunello wine country exploration complement refreshing dips in the seasonal waters.
$119 nightly
The price is $140
Nov 12 - Nov 13
Total with taxes and fees
SI Montalcino Hotel
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 Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"This is a very special place. A highlight of our trip. The service was top notch and the staff worked hard to make sure that our time there was a great experience. We had two dinners there and both were delicious. The room was very comfortable. They even gifted us with their branded olive oil when we checked out. We were sad to leave!"
Edward 2-night trip
Posted 2 days ago
Hotel Certosa Di Maggiano

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 9 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 Relais II Chiostro di Pienza: Features a rooftop terrace, a seasonal outdoor pool, and daily. Hotel Corsignano: Provides complimentary wireless internet access, a seasonal outdoor pool, and Smart TVs. Hotel San Gregorio: Features buffet, a seasonal outdoor pool, and free self parking. Tenuta Santo Pietro: Offers buffet, a seasonal outdoor pool, and free self parking. Podere Spedalone: Features a rooftop terrace, an outdoor pool, and full.
How many hotels with pools are there in Pienza?
Expedia has 9 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 RI Crea RE. 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.

Explore a world of travel with Expedia