The Best Family Hotels in Pienza from AED 344 in 2026 | Expedia

A historic square with a prominent tower and statues.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Pienza Family Hotels

Tonight

19 Oct - 20 Oct

Tomorrow

20 Oct - 21 Oct

This weekend

23 Oct - 25 Oct

Next weekend

Our top choices for Pienza family-friendly hotels

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A bathroom with a toilet, bidet, sink, and shower.

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

A buffet setup with various food items and condiments.

1. Relais Cloister Pienza

Pienza

AED 473

AED 545 total

includes taxes & fees

20 Oct - 21 Oct

Two people sitting at a round table outdoors with a scenic view of mountains in the background.

A breakfast buffet with various food items and beverages.

A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.

A patio area with wicker furniture, a glass table, and a pool in the background.

2. Hotel Corsignano

Pienza

Families find paradise with babysitting services, bicycle rentals, and two hot tubs just steps from Pienza's historic treasures.

AED 480

AED 552 total

includes taxes & fees

10 Nov - 11 Nov

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A swimming pool with a water feature, surrounded by greenery and a table with chairs.

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.

3. Hotel San Gregorio

Pienza

Tuscan residence welcomes families with outdoor pool, hot tubs, and optional babysitting services just steps from Palazzo Piccolomini.

AED 472

AED 544 total

includes taxes & fees

8 Nov - 9 Nov

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 stone building with a gravel pathway leading to the entrance.

4. 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 488

AED 553 total

includes taxes & fees

19 Nov - 20 Nov

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 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

Pienza

AED 718

AED 807 total

includes taxes & fees

21 Oct - 22 Oct

A room with a green cabinet, a mirror, a sink, and a television.

A patio area with outdoor seating, potted plants, and a view of the landscape.

A cozy dining area with a table set for four, surrounded by wooden chairs and a patterned tablecloth.

A cozy living room with a fireplace, a dining area, and a black leather chair.

6. Affitacamere Maria Gabriella

Pienza

AED 400

AED 543 total

includes taxes & fees

28 Oct - 29 Oct

An outdoor dining area with wooden tables and benches, stone walls, and greenery.

A modern interior with a white sofa, wooden coffee table, and bookshelves filled with books.

A modern living room with a white sofa, a coffee table, and a bookshelf.

A courtyard with a stone building, arched openings, and a covered seating area.

7. La Bandita Townhouse

Pienza

AED 1,587

AED 1,763 total

includes taxes & fees

3 Nov - 4 Nov

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.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

8. Tenuta Santo Pietro

Pienza

AED 851

AED 953 total

includes taxes & fees

25 Oct - 26 Oct

View all properties

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

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

Relais Cloister Pienza

Pienza

AED 473

AED 545 total

includes taxes & fees

20 Oct - 21 Oct

Two people sitting at a round table outdoors with a scenic view of mountains in the background.

A breakfast buffet with various food items and beverages.

A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.

A patio area with wicker furniture, a glass table, and a pool in the background.

Hotel Corsignano

Pienza

AED 480

AED 552 total

includes taxes & fees

10 Nov - 11 Nov

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A swimming pool with a water feature, surrounded by greenery and a table with chairs.

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.

Hotel San Gregorio

Pienza

AED 472

AED 544 total

includes taxes & fees

8 Nov - 9 Nov

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 stone building with a gravel pathway leading to the entrance.

Agriturismo Il Macchione

Pienza

AED 488

AED 553 total

includes taxes & fees

19 Nov - 20 Nov

A patio area with outdoor seating, potted plants, and a view of the landscape.

A cozy living room with a fireplace, a dining area, and a black leather chair.

A bedroom with a bed, a nightstand, a lamp, a chair, a table, and a window with a view of greenery.

A cozy dining area with a table set for four, surrounded by wooden chairs and a patterned tablecloth.

Affitacamere Maria Gabriella

Pienza

AED 400

AED 543 total

includes taxes & fees

28 Oct - 29 Oct

An outdoor dining area with wooden tables and benches, stone walls, and greenery.

A modern interior with a white sofa, wooden coffee table, and bookshelves filled with books.

A modern living room with a white sofa, a coffee table, and a bookshelf.

A courtyard with a stone building, arched openings, and a covered seating area.

La Bandita Townhouse

Pienza

AED 1,587

AED 1,763 total

includes taxes & fees

3 Nov - 4 Nov

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.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

Tenuta Santo Pietro

Pienza

AED 851

AED 953 total

includes taxes & fees

25 Oct - 26 Oct

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 dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.

Hotel Rutiliano Centro Benessere

Pienza

AED 718

AED 807 total

includes taxes & fees

21 Oct - 22 Oct

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 cozy reading room with a fireplace, bookshelves, and comfortable seating.

A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.

L'Olmo

Pienza

AED 1,651

AED 1,833 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

Podere Spedalone

Pienza

AED 566

AED 639 total

includes taxes & fees

29 Oct - 30 Oct

View all properties

Family-friendly hotels with pools in Pienza

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

Relais Cloister Pienza

Pienza

AED 473

AED 545 total

includes taxes & fees

20 Oct - 21 Oct

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

A swimming pool with a water feature, surrounded by greenery and a table with chairs.

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.

Hotel San Gregorio

Pienza

AED 472

AED 544 total

includes taxes & fees

8 Nov - 9 Nov

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 stone building with a gravel pathway leading to the entrance.

Agriturismo Il Macchione

Pienza

AED 488

AED 553 total

includes taxes & fees

19 Nov - 20 Nov

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.

An outdoor dining area with tables set for two, surrounded by chairs, and large windows offering a view of the greenery outside.

Tenuta Santo Pietro

Pienza

AED 851

AED 953 total

includes taxes & fees

25 Oct - 26 Oct

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 dining area with tables and chairs, a buffet with various food items, and large windows offering a view of trees.

Hotel Rutiliano Centro Benessere

Pienza

AED 718

AED 807 total

includes taxes & fees

21 Oct - 22 Oct

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 cozy reading room with a fireplace, bookshelves, and comfortable seating.

A bedroom with a canopy bed, wooden flooring, a bedside table, and a built-in bookshelf.

L'Olmo

Pienza

AED 1,651

AED 1,833 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

Podere Spedalone

Pienza

AED 566

AED 639 total

includes taxes & fees

29 Oct - 30 Oct

A large, single-story building with a tiled roof, a covered patio area with outdoor seating, and a well-maintained lawn.

A two-story building with a flat roof and a small balcony on the second floor.

A building with a window, a gravel path, and a flower bed with red and pink flowers.

A bedroom with a four-poster bed, a wooden cabinet, and a window with lace curtains.

Agriturismo Poggio Tobruk

Pienza

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

"By the time you check out. You feel like you are saying goodbye to family. This hotel goes above and beyond for their guests. From Michelle, Lorenzo, Faith, etc. the whole team made out stay 5/5+. We cannot wait to go back!"

Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent

"It's a lovely hotel, but it is the staff that make it truly special. Attentive and cheerful, I felt well looked after from the moment I walked in. Wonderful stay, I'll definitely be back."

Hotel Corsignano

Hotel Corsignano

10/10 Excellent

"Love this hotel. Very nice place in a great location and very friendly staff."

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"This was an amazing stay recommended by a friend and we really loved this place. The only immediate issues were the A/C broke and the TV was hard to setup, and the toilet seat was cracked and broke when I sat on it. But they fixed all that on day 1 and we had an amazing time - staff was amazing, grounds, parking, quiet, romantic, everything. The restaurant was amazing wine cellar. The food a little exotic so if you want more basic - then head over to Cortona with a car 15 min drive up the hill. Best part of trip was having a car. The people amazing, Daniel, Enrico, and cant remember everyone - everyone was amazing."

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"La vue est panoramique et le château est grandiose"

Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent

"Get"

Tenuta Santo Pietro

Tenuta Santo Pietro

10/10 Excellent

"Tenuta Santo Pietro is truly a hidden gem, but what makes it so special is Bertina. She is, without a doubt, one of the most wonderful people I have ever encountered in all my years of traveling. Her warmth, kindness, attentiveness, and genuine love for what she does made our entire stay unforgettable. She goes above and beyond in every way and makes you feel so welcomed and cared for. I honestly cannot say enough wonderful things about her! The property is beautiful, the rooms are spacious, and the beds are incredibly comfortable. The restaurant is also absolutely incredible. After 10 days traveling throughout Italy, some of our favorite meals of the entire trip were here. From the exceptional wine to the pasta, desserts, and everything in between, every meal felt special. Tenuta Santo Pietro is a magical place, and Bertina is the heart of it. She made our stay truly unforgettable, and I cannot wait to return. I only hope she will be there to welcome us again. I have stayed in many wonderful places, but it is rare to meet someone who leaves such a lasting impression. Bertina is an absolute gem, and this property is so lucky to have her!"

Fonteverde Thermal Spa Resort Tuscany

Fonteverde Thermal Spa Resort Tuscany

10/10 Excellent

"Our third stay here. It’s so nice. The town is also quaint too."

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 Agriturismo Il Macchione and Podere Spedalone.

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 Museo Diocesano. Make sure you have lots of time for activities like Palazzo Borgia and Artemisia Gallery.