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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 $126 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,510 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, Wi-Fi and Pool across Pienza rentals

  • 4.6 Average rating

    Pienza stays receive an average rating of 4.6 out of 5 from guests

Top-rated family-friendly rentals in Pienza

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia

Agriturismo Poggio Bicchieri ap. Memoria

Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!

Indoor spacesFamilyAir conditioning

4.92 out of 5 average rating, 626 reviews
Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 251 reviews
Top Guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano

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

KitchenFamilyAccess

4.98 out of 5 average rating, 165 reviews
Guest favourite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Indoor spacesKitchenBathroom

4.95 out of 5 average rating, 146 reviews
Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

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

KitchenIndoor spacesCheck-in

4.93 out of 5 average rating, 335 reviews
Guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona

Casa Dolce Toscana | Panoramic Suite & View

CASA DOLCE TOSCANA 🖼️ Ciao! Sono Jolanta 😊 Benvenuti nel nostro amato alloggio toscano ,con vista panoramica,immerso nelle colline della Toscana.Un’oasi di pace perfetta per chi desidera rilassarsi e vivere un’esperienza autentica. Situato a pochi chilometri da Siena e Firenze,il nostro alloggio combina il fascino rustico con tutti i comfort moderni. si trova nel cuore del centro storico del famoso borgo di Cetona,sottostante al castello ,con vista sulla valle e il profumo della Toscana.

KitchenIndoor spacesLocation

4.98 out of 5 average rating, 185 reviews
Guest favourite
Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.
Farm stay in Montepulciano

Tuscan farmhouse stay with restaurant and pool

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.

Indoor spacesKitchenLayout

4.94 out of 5 average rating, 107 reviews
Top Guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci

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.

KitchenFamilyBarbecue

5.0 out of 5 average rating, 116 reviews
Top Guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home in San Quirico d'Orcia

Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

KitchenIndoor spacesAccuracy

4.99 out of 5 average rating, 232 reviews
Top Guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello

In Toscana Camere

**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.

FamilyKitchenOutdoor spaces

4.96 out of 5 average rating, 137 reviews
Guest favourite
A welcoming dining area features a wooden table set with plates and glassware, accompanied by fresh fruit. A bouquet of flowers sits on an adjoining console, while a television displays scenic imagery against a warm, yellow wall illuminated by wall-mounted lighting.
Home in Pienza

Spacious Luxury Stay in Pienza | 3BR 3BA

Scopri un rifugio elegante, spazioso e autentico nel cuore di Pienza, gioiello rinascimentale Patrimonio UNESCO. Con 3 camere matrimoniali, 3 bagni, ampia zona living, cucina attrezzata, A/C e Wi-Fi, questa casa è perfetta per famiglie o amici che desiderano vivere la Toscana più iconica tra vicoli storici, sapori unici e panorami indimenticabili sulla Val d’Orcia, con tutto il comfort di una dimora davvero speciale.

Indoor spacesKitchenDecor

4.97 out of 5 average rating, 101 reviews
Top Guest favourite
A rustic agriturismo is framed by vibrant greenery and blooming flowers. Outdoor seating is provided by several light-colored chairs and a patterned table. The stone building showcases large windows, which invite natural light into the space, while a welcoming atmosphere is suggested by the well-maintained garden.
Farm stay in Pienza

Castello di Spedaletto, Val d'Orcia, Pienza

L'agriturismo Castello di Spedaletto sorge nell’edificio che un tempo ospitava il granaio dell’antico castello medioevale ed è stato recentemente ristrutturato in perfetto equilibrio tra modernità e tradizione: pietra, mattoni, travi a vista si fondono con la caratteristica scalinata in cristallo e ferro battuto. L'agriturismo è formato da 5 camere matrimoniali con bagno e 2 appartamenti. Vieni, Vedi, Vivi…

KitchenFamilyGetting around

4.97 out of 5 average rating, 185 reviews

Popular amenities for Pienza family-friendly rentals

Family-friendly home rentals with a hot tub

Family- and pet-friendly home rentals

Top Guest favourite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

Casale in pietra in Val D’Orcia

FamilyIndoor spacesWalkability

4.98 out of 5 average rating, 160 reviews
Guest favourite
Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.
Apartment in Monticchiello

Casa Bonari - un paradiso per gli occhi

KitchenFamilyComfort

4.97 out of 5 average rating, 187 reviews
Top Guest favourite
A cozy bedroom features a spacious bed with neutral-toned linens and decorative pillows. The warm yellow walls are adorned with framed photographs, while shelves hold books and small decorative items. Soft lighting enhances the inviting atmosphere, creating a comfortable space for relaxation.
Condo in Pienza

Casa Gioia

Indoor spacesKitchenParking

4.92 out of 5 average rating, 150 reviews
Top Guest favourite
Condo in Pienza

Amazing view of Val d'Orcia Pienza

FamilyIndoor spacesLocation

4.92 out of 5 average rating, 126 reviews
Top Guest favourite
A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.
Apartment in Castiglione d'Orcia

Appartamento Mimosa - Poggio al Vento

FamilyKitchenLayout

4.99 out of 5 average rating, 112 reviews
Guest favourite
Farm stay in Castelnuovo Berardenga

Apartment in a Tuscan farmhouse at Le Pietre Vive

KitchenFamilyBreakfast

4.92 out of 5 average rating, 359 reviews
Top Guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano

La Piazzetta -Accogliente open space nel centro storico di Montepulciano

Indoor spacesKitchenWi-Fi

5.0 out of 5 average rating, 514 reviews
Top Guest favourite
A well-maintained garden area is featured, showcasing a barbecue grill, picnic tables, and lounge chairs under a shaded canopy. Verdant olive trees and rolling hills can be seen in the background, with a distant view of the historic town above.
Farm stay in Montepulciano

Agriturismo Pescaia Montepulciano Appartamento 2

Indoor spacesKitchenSleep quality

4.97 out of 5 average rating, 169 reviews

Family-friendly home rentals with a pool

Top Guest favourite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Apartment in Montalcino

Panoramic Country Suite Montalcino

FamilyKitchenBarbecue

4.9 out of 5 average rating, 406 reviews
Top Guest favourite
A wooden dining table is set in a lush green garden, surrounded by blooming flowers. Sun loungers and umbrellas line the pool area, with a distant view of rolling hills under a clear blue sky.
Farm stay in Pienza

Piandimaggio family and friends

Indoor spacesKitchenLocation

4.88 out of 5 average rating, 328 reviews
Top Guest favourite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano

A paradise in Montepulciano...

KitchenFamilyPool

4.96 out of 5 average rating, 168 reviews
Top Guest favourite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

FamilyIndoor spacesAir conditioning

4.99 out of 5 average rating, 118 reviews
Guest favourite
A warm and inviting open space features a wooden dining table surrounded by chairs, illuminated by natural light from several windows. A red sofa is positioned nearby, while a television and kitchen appliances, including a stove and oven, are visible in the background.
Apartment in Montepulciano

Casa Crociani - Amazing Pool & Free Parking

KitchenFamilyAccuracy

4.93 out of 5 average rating, 129 reviews
Top Guest favourite
Apartment in Castiglione del Lago

Farmhouse close to Montepulciano

KitchenIndoor spacesCleanliness

4.88 out of 5 average rating, 144 reviews
Top Guest favourite
An aerial view captures the agriturismo surrounded by lush green fields and a neatly arranged row of tall cypress trees. The inviting pool reflects the serene landscape, and the winding dirt road leads towards the property, nestled amid the picturesque Crete Senesi.
Apartment in Asciano

Loggiato 1 in agriturismo con piscina condivisa

Indoor spacesKitchenAir conditioning

4.97 out of 5 average rating, 188 reviews
Top Guest favourite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Apartment in Monteriggioni

Comfort Apartment tra i vigneti del Chianti

KitchenIndoor spacesQuiet

4.93 out of 5 average rating, 455 reviews

When is the best time to visit Pienza?

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Avg. price$218 AUD$215 AUD$242 AUD$244 AUD$253 AUD$271 AUD$229 AUD$233 AUD$230 AUD$227 AUD$236 AUD$229 AUD
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