
Family-friendly holiday rentals in Pienza
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Pienza

Total holiday rentals
Explore 30 holiday rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at $128 AUD per night before taxes and fees

Verified guest reviews
Over 1,380 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Pienza holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pienza rentals

4.9 Average rating
Pienza stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Pienza
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
Indoor spacesFamilyLong stay

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.
Indoor spacesKitchenNearby

Villa with View for Family & Friends, in Tuscany
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!
KitchenIndoor spacesLong stay

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away
FamilyIndoor spacesLong stay

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking
Indoor spacesKitchenGetting around

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.
KitchenIndoor spacesView
La Piazzetta - Cozy open space in the historic center of Montepulciano
Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.
FamilyIndoor spacesWi-Fi

Flat, Agriturismo "Biofattoria l'Upupa"
The flat is on the first floor of a classic Tuscan farmhouse called ‘Biofattoria l'Upupa’. Magnificent hillside location between the Val d'Orcia and the Crete Senesi. Suitable for families with children. Consisting of kitchen, large living room, bathroom with shower, 1 double bedroom and 1 bedroom with bunk beds. There is a double sofa bed in the living room. The flat is equipped with wifi. Free parking on private property. Complete breakfast kit including homemade cakes.
Indoor spacesFamilySleep quality

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?
Indoor spacesFamilyLayout

At the Arch - In the Heart of the Val D'Orcia
Scopri il fascino autentico della Toscana soggiornando in un accogliente e curato appartamento all'ingresso del centro storico situato sulle mura della città di Pienza, nel cuore della splendida Val D'Orcia. Un rifugio perfetto per chi cerca relax, bellezza e atmosfera, circondato da uno dei paesaggi più iconici di Italia. L'appartamento, ideale fino a 3 ospiti, combina semplicità e confort per offrirti un soggiorno piacevole e rilassante.
Indoor spacesFamilyCondition

In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.
FamilyKitchenHospitality

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza
Farmhouse Palazzo del Papa, with an apartment with 3 double bedrooms, 2 bathrooms, 1 fully equipped kitchen, a large living room, equipped with air conditioning, to spend time with friends or family. On request breakfast and dinner with the products of our farm. Garden and wi-fi for our guests.
FamilyKitchenLaundry
Popular amenities for Pienza family-friendly rentals
Family-friendly home rentals with a hot tub

White lily with a view of Siena
Indoor spacesKitchenHospitality

Villa in Montepulciano with a Pool
FamilyIndoor spacesCheckout

Villa di Geggiano – Guesthouse
Indoor spacesKitchenCleanliness

RESIDENCE HILL
KitchenFamilyAmenities

Casa al Gianni - The Simignano Barn
KitchenFamilyHot tub

Villa unesco heritage, Jacuzzi & garden. BB Daria
Indoor spacesKitchenBreakfast

La Pieve - the house next to the church
Indoor spacesFamilyCleanliness

La Casetta di Nise, Private Spa in the Hamlet
Indoor spacesKitchenHospitality
Family- and pet-friendly home rentals

Tuscan cottage with an heavenly view
Indoor spacesKitchenBathroom

The Eagle and the Olive Tree
KitchenIndoor spacesGetting around

Celeste – The color of the summer sky in Tuscany
Indoor spacesKitchenOutdoor spaces

Stuart White Tea Central Panoramic & Garden
Indoor spacesFamilyGetting around

Casa Gioia
FamilyIndoor spacesQuiet

I Tramonti di Eramo, central Montepulciano.
KitchenIndoor spacesAccess

Casa Bonari - a paradise for the eyes
Indoor spacesFamilyBreakfast

Amazing view of Val d'Orcia Pienza
FamilyIndoor spacesAccess
Family-friendly home rentals with a pool

Tuscan Villa Pienza: stunning views and pure relax
FamilyKitchenQuiet

Farmhouse close to Montepulciano
FamilyKitchenView

Apt 4: Montepulciano 800 yr old Monastery
KitchenFamilyComfort

Casa Biancospino Crete Senesi | Podere Fossaccio
Indoor spacesFamilyCondition

Casa Crociani - Amazing Pool & Free Parking
Indoor spacesKitchenBathroom

Country chic house in a village,private pool,wiFi
KitchenIndoor spacesOutdoor spaces

La Rimbecca Farmhouse, Gli Archi
Indoor spacesKitchenHospitality

Elegant farmhouse Siena
KitchenFamilyBiking
When is the best time to visit Pienza?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $221 AUD | $218 AUD | $245 AUD | $217 AUD | $235 AUD | $211 AUD | $232 AUD | $237 AUD | $234 AUD | $231 AUD | $240 AUD | $232 AUD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Centro Storico Orvieto
- Terme Dei Papi
- Cascate del Mulino
- La Scarzuola
- Avignonesi Winery Fattoria Le Capezzine
- Siena Cathedral
- Palazzo Pubblico
- Terme San Filippo
- Antinori nel Chianti Classico
- Ugolino Golf Club
- Vulci
- Mount Amiata
- Val di Chiana
- Valdichiana Outlet Village
- Abbey of Sant'Antimo
- Saturnia Thermal Park
- Riserva Naturale Diaccia Botrona
- Santa Maria della Scala





