
Family-friendly vacation rentals in Pienza
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Pienza
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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

Stuart Black Tea Amazing View & Super Central
This apartment is in a prime central location and enhanced by an abundance of natural light and awe-inspiring panoramic vistas. It features one double bedroom, a panoramic living room, a bathroom with shower, and a spacious kitchen. Its advantageous proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Additionally, guests will have access to a backyard garden, creating an ideal setting for savouring a glass of wine

Luxurious Medieval Tower & Private Concierge
It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Montepulciano Historic Center
Nice 60-square-meter apartment located on the main street of the town. It is located on the second and top floor of a historic building. The entrance is located on the main street of the town while the windows face the outside of the walls offering a breathtaking view. The apartment consists of: an entrance, a living room with a double sofa bed, a bedroom, a kitchen, and a bathroom with a roof window. It is equipped with a microwave, large oven, dishwasher, washing machine and wifi.

Studio (2+1) in Val d'Orcia - Tuscany
A few steps from the historic center of medieval San Quirico d'Orcia and just 100 meters from the supermarket, a stay made of silence and the quiet passage of time, of days with a relaxing and regenerating atmosphere characteristic of the lifestyle in Val d'Orcia. The Taste of Tranquility is guaranteed by a 5000 sqm park that offers lawns and shady trees suitable for reading or simple relaxation. Ideal for a stay with an "antique" flavor", combined with all modern comforts.

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Podere Pereti Nuovi – Modern Tuscan Villa
Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

Casa Bonari - a paradise for the eyes
Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

Casa Gioia
My place is located in the historic center of Pienza, on the second floor without an elevator. It overlooks the main street of Pienza. The nearest paid parking lots are 150m away, the free ones 300m, loading/unloading area 50m. You'll love my place because of the comfort of the bed, the intimacy, the wooden-beam ceilings, and the typical terracotta floor. My place is good for couples, business travelers, and families (with kids)

Pienzalettings
Rilassati in questo spazio tranquillo nel piccolo borgo. La nostra casa vacanze PienzaLettings è un'esplosione di unicità e bellezza, dotata di un fascino senza tempo. Dotato di ogni comfort, è pronto ad accogliervi e pronto a farvi vivere un'avventura rilassante ed emozionante in un luogo senza tempo. Non sono inclusi 1€ di tassa di soggiorno per persona a notte, esclusi minori di 15 anni

Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Amazing view of Val d'Orcia Pienza
Beautiful 75-square-meter apartment located on the ground floor of the “Podere Colombaio,” a historic farmhouse named after its 15th-century tower. The property features a lovely pergola and a garden overlooking the Val d’Orcia Park, just a 10-minute walk from Pienza.
Popular amenities for Pienza family-friendly rentals
Family-friendly home rentals with a hot tub

Amazing Tuscany Villa, FREE parking

"Sunflower" apartment with view of Siena

San Giovanni in Poggio, Villa Meriggio 95 sqm

Villa in Montepulciano with a Pool

Villa di Geggiano – Guesthouse

Poggio dell'orso.Traditional Casale. Amazing views

La Pieve - the house next to the church

Montalcino Townhouse with Private Garden & Spa
Family- and pet-friendly home rentals

Tuscan cottage with an heavenly view

agriturismo il poderuccio "sweet apartment"

Agriturismo Pescaia Montepulciano Apartment 2

Resort Panoramic view - Free parking

Romantic Pienza Valdorcia The Tower of S.Guglielmo

"Dimora Valinda" Montepulciano Piazza Grande + A/C

Rosemary

Il Focolare - Superior Tuscany Apartment
Family-friendly home rentals with a pool

Panoramic Country Suite Montalcino

The Eagle and the Olive Tree

Loggia 1 in farmhouse with shared pool

Esplora la natura al centro di Vigneti Chianti

Casa Crociani - Amazing Pool & Free Parking

Poggio ai Gelsi, Ginestra Lodge

Romantic apartment in a quite place

Piandimaggio family and friends
When is the best time to visit Pienza?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$28,027 GYD | G$28,236 GYD | G$33,465 GYD | G$31,792 GYD | G$34,511 GYD | G$30,955 GYD | G$34,093 GYD | G$34,720 GYD | G$34,302 GYD | G$33,884 GYD | G$35,139 GYD | G$34,093 GYD |
| 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 |
Quick stats about vacation rentals that are family-friendly in Pienza

Total vacation rentals
Explore 30 vacation rentals in Pienza

Nightly prices starting at
Pienza vacation rentals start at G$16,733 GYD per night before taxes and fees

Verified guest reviews
Over 1,350 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
20 of Pienza vacation 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!
Destinations to explore
- Provence Vacation rentals
- Rome Vacation rentals
- Molfetta Vacation rentals
- Milan Vacation rentals
- Nice Vacation rentals
- Florence Vacation rentals
- Venice Vacation rentals
- Naples Vacation rentals
- Francavilla al Mare Vacation rentals
- Italian Riviera Vacation rentals
- Cannes Vacation rentals
- Bologna Vacation rentals
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cala Violina
- Cascate del Mulino
- Avignonesi Winery Fattoria Le Capezzine
- Terme Dei Papi
- Basilica of St Francis
- Santa Maria della Scala
- Palazzo Pubblico
- Siena Cathedral
- Antinori nel Chianti Classico
- Riserva Naturale Diaccia Botrona
- Rocca Maggiore
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Saturnia Thermal Park
- Castello di Verrazzano
- Parco Regionale Della Maremma
- Girifalco Fortress
- Pozzo di San Patrizio
- Terme San Filippo
- Vulci
- Cathedral of San Lorenzo




