A historic square with a prominent tower and statues.

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Check availability on Pienza Family Hotels

Tonight
4 Sep - 5 Sep
Tomorrow
5 Sep - 6 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

Our top choices for Pienza family-friendly hotels

1. Hotel Corsignano

Hotel Corsignano
Pienza
  • Families find paradise with babysitting services, bicycle rentals, and two hot tubs just steps from Pienza's historic treasures.
AED 755
AED 856 total
includes taxes & fees
23 Sep - 24 Sep
Hotel Corsignano

2. Hotel San Gregorio

Hotel San Gregorio
Pienza
  • Tuscan residence welcomes families with outdoor pool, hot tubs, and optional babysitting services just steps from Palazzo Piccolomini.
AED 886
AED 1,001 total
includes taxes & fees
6 Sep - 7 Sep
Hotel San Gregorio

3. Podere Spedalone

Podere Spedalone
Pienza
  • This Tuscan farm stay delights families with seasonal outdoor pool, hiking trails, and complimentary breakfast buffet each morning.
AED 630
AED 710 total
includes taxes & fees
5 Oct - 6 Oct
Podere Spedalone

4. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
  • Splash into family fun at this Pienza retreat where kids adore the playground while parents unwind poolside at the winery.
AED 1,657
AED 1,840 total
includes taxes & fees
28 Sep - 29 Sep
Agriturismo Il Macchione

5. L'Olmo

L'Olmo
Pienza
AED 2,681
AED 2,966 total
includes taxes & fees
17 Sep - 18 Sep
L'Olmo

6. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
AED 772
AED 1,020 total
includes taxes & fees
15 Sep - 16 Sep
Suite Gioconda - Podere Casa Rossa in Pienza

7. Il Podere di Casa Rossa Pienza

Il Podere di Casa Rossa Pienza
Pienza
AED 1,008
AED 1,379 total
includes taxes & fees
5 Oct - 6 Oct
Il Podere di Casa Rossa Pienza

8. Podere Manafiore - historical villa with swimming pool

Podere Manafiore - historical villa with swimming pool
Monticchiello
Podere Manafiore - historical villa with swimming pool

9. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
AED 697
AED 780 total
includes taxes & fees
6 Sep - 7 Sep
Borgo Sant'Ambrogio Resort

10. Locanda Vesuna

Locanda Vesuna
Trequanda
  • Immerse in family poolside fun at this Tuscan hotel with kids' playground, game room, and seasonal rooftop swimming.
AED 470
AED 530 total
includes taxes & fees
1 Oct - 2 Oct
Locanda Vesuna
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Choose what matters most at family-friendly hotels in Pienza

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with free breakfast in Pienza

Hotel Corsignano

Hotel Corsignano
Pienza
AED 755
AED 856 total
includes taxes & fees
23 Sep - 24 Sep
Hotel Corsignano

Hotel San Gregorio

Hotel San Gregorio
Pienza
AED 886
AED 1,001 total
includes taxes & fees
6 Sep - 7 Sep
Hotel San Gregorio

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
AED 414
AED 562 total
includes taxes & fees
4 Oct - 5 Oct
Affitacamere Maria Gabriella

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
AED 1,657
AED 1,840 total
includes taxes & fees
28 Sep - 29 Sep
Agriturismo Il Macchione

L'Olmo

L'Olmo
Pienza
AED 2,681
AED 2,966 total
includes taxes & fees
17 Sep - 18 Sep
L'Olmo

Podere Spedalone

Podere Spedalone
Pienza
AED 630
AED 710 total
includes taxes & fees
5 Oct - 6 Oct
Podere Spedalone
View all properties

Family-friendly hotels with pools in Pienza

Hotel San Gregorio

Hotel San Gregorio
Pienza
AED 886
AED 1,001 total
includes taxes & fees
6 Sep - 7 Sep
Hotel San Gregorio

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
AED 1,657
AED 1,840 total
includes taxes & fees
28 Sep - 29 Sep
Agriturismo Il Macchione

Podere Spedalone

Podere Spedalone
Pienza
AED 630
AED 710 total
includes taxes & fees
5 Oct - 6 Oct
Podere Spedalone

L'Olmo

L'Olmo
Pienza
AED 2,681
AED 2,966 total
includes taxes & fees
17 Sep - 18 Sep
L'Olmo

Podere Manafiore - historical villa with swimming pool

Podere Manafiore - historical villa with swimming pool
Monticchiello
Podere Manafiore - historical villa with swimming pool
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.
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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
"Such a fantastic property, the most amazing food and great surroundings. Just a thoroughly lovely experience."
Rushab 3-night trip
Posted 23 hours ago
Villa di Piazzano - Small Luxury Hotel of the World
Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"AC , I think the entire building gets turned down in the evening, regardless of what we set the temperature in the room to. Excellent location. Walking distance to the main square. Very spacious. Room as presented in the photos"
Debora 1-night trip
Posted 1 day ago
Hotel Corsignano
Castello di Leonina Relais

Castello di Leonina Relais

10/10 Excellent
"We stayed 4 days and are so glad we stayed here. The area has a restaurant right outside with the best view where they serve lunch and dinner. They also have a bar and a pool. It’s an old castle and yet they keep it clean and pretty restored. Breakfast buffet in the morning was included for us. The bathroom comment from others might be from not understanding how to use it as you have to pump the button several times to flush. The staff was wonderful and helpful. They spoke English and some Spanish."
Mariela 4-night trip
Posted 7 days ago
Castello di Leonina Relais
Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent
"Such a wonderful stay. The view is breathtaking and Bertina and her team delightful. Our favorite place in Tuscany."
Annie 2-night trip
Posted 9 days ago
Tenuta Santo Pietro
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 3 weeks ago
Castello di Velona Resort Thermal SPA & Winery
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Best hotel ever."
Ray 2-night trip
Posted 2 months ago
Castiglion del Bosco, A Rosewood Hotel
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

What's Pienza like for family-friendly vacations?
The destination of Pienza is a good option if you've been considering a getaway with the kids. The castle here makes this an attractive vacation spot for families.
What's the best accommodation for a family vacation in Pienza?
Hotel Corsignano is a hotel with a restaurant and free parking, and it's a top choice on Expedia for families. Other good choices to stay with the kids include Podere Spedalone and Agriturismo Il Macchione.
How many family-friendly hotels are there in Pienza?
Expedia has 9 family-friendly hotels and other accommodations in Pienza.
When's the best time to book a family-friendly vacation in Pienza?
The hottest months are usually August and July with an average temp of 69°F, while the coldest months are January and February with an average of 42°F. Average annual precipitation for Pienza is 42 inches.
What's there to see and do with your family in Pienza?
While you are visiting Pienza, you might want to round up the kiddos and make time to see interesting attractions such as Palazzo Piccolomini, Historic Centre of Pienza, and Artemisia Gallery. Make sure you have lots of time for activities like Museo Diocesano and Palazzo Borgia.