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Family-friendly holiday 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.

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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
4.97 out of 5 average rating, 122 reviews

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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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
4.97 out of 5 average rating, 203 reviews

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.

Top Guest favourite
A vibrant garden features an array of colorful flowers, with delicate white blooms prominently displayed. In the background, rolling hills are seen under a dramatic sky, creating a serene landscape filled with natural beauty.
Home in Castiglione d'Orcia
4.95 out of 5 average rating, 108 reviews

Da nonna Ornella - nido in Val d’Orcia

Vista spettacolare e relax assicurato in questo romantico monolocale nel cuore della Val d’Orcia, provincia di Siena, immerso nella splendida Toscana. Ideale per coppie. Dispone di zona living, cucina accessoriata, bagno, riscaldamento, resede, parcheggio privato e un grande e panoramico giardino con lettini e amaca. Vicino a mete iconiche: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d’Orcia, Radicofani, Castiglione d’Orcia e Monte Amiata. Indimenticabile!

Top Guest favourite
A dog sits in a grassy area, observing the expansive vineyard landscape that unfolds beyond, featuring rolling hills and rows of grapevines under soft morning light.
Farm stay in Montepulciano
4.95 out of 5 average rating, 202 reviews

Separate room, between Cortona and Montepulciano

We are a small farm with a family-run farm on the border between Tuscany and Umbria. The old farmhouse in which we live with our children are surrounded by vineyards and olive groves with a splendid view of Montepulciano. We can sleep in 2 apartments and / or 1 independent room furnished with poor art and originality. In the large garden, available to all, there are two pools (one for children), games, organic vegetable garden. We have a restaurant Pierpaolo cooking the typical Tuscan dishes.

Top 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
4.99 out of 5 average rating, 108 reviews

Casa Dolce Toscana~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.

Top Guest favourite
A wooden table is set with two cream-colored cups and a small vase filled with dried wheat and decorative grasses. The white brick wall creates a warm backdrop, enhancing the inviting atmosphere of the dining area.
Apartment in Montepulciano
4.99 out of 5 average rating, 271 reviews

Montepulciano Centro Storico

Grazioso appartamento di 60 mq situato nel corso principale del paese. Si trova al secondo ed ultimo piano di un palazzo storico. L'ingresso è situato sul corso principale della cittadina mentre le finestre si affacciano verso l'esterno delle mura offrendo un vista mozzafiato. L'appartamento è composto da: ingresso, soggiorno con divano letto matrimoniale, camera da letto, cucina, bagno con finestra a tetto. E' dotato di forno a microonde, forno grande, lavastoviglie, lavatrice e wi-fi.

Guest favourite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Apartment in Montepulciano
4.98 out of 5 average rating, 134 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Top 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
4.97 out of 5 average rating, 169 reviews

Casa Bonari - un paradiso per gli occhi

Casa Bonari è un appartamento indipendente su un unico livello all'interno di una villa ai piedi di Monticchiello. E' composto da 3 camere da letto, 2 bagni, cucina attrezzata e salotto. Le stanze sono luminose e arredate in stile toscano, con vecchi mobili di famiglia ristrutturati uniti ad elementi contemporanei. La cucina è completamente attrezzata e l'appartamento circondato su ogni lato da un grande giardino, così che tutte le stanze vantano un bellissimo panorama sulla campagna.

Top Guest favourite
An aerial view captures the property nestled in a scenic landscape, surrounded by rolling hills and cultivated fields. Olive groves line the winding road, with cypress trees dotting the surroundings, showcasing the natural beauty of the Tuscan countryside.
Condo in Asciano
4.97 out of 5 average rating, 319 reviews

Verde - I prati in Toscana

Appartamento composto da 1 camera matrimoniale , cucina attrezzata, ampio soggiorno e bagno Tv, BBq, ( mettiamo a disposizione la lavatrice dalle 9 alle 20 che è nella nostra lavanderia a chi ne fa richiesta ) . Consigliamo l'auto in quanto abitiamo in campagna, sia per essere indipendenti , sia per visitare la magnifica toscana Ti piacerá l'ambiente esterno perché é magico di giorno e di notte Parcheggio e wifi gratis Posizione strategica per visitare la Toscana e l'Umbria.

Top Guest favourite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay in Seggiano
4.99 out of 5 average rating, 262 reviews

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Guest favourite
The countryside property is nestled among lush greenery, featuring rustic architecture and terracotta roofs. Surrounded by rolling hills and trees, the natural landscape creates a peaceful setting. A gravel path leads to the house, enhancing the connection to the serene outdoor environment.
Farm stay in Sovicille
4.93 out of 5 average rating, 160 reviews

Casa al Gianni - Olmo

Ciao, siamo Cristina & Carmelo! Ti invitiamo a scoprire il fascino rustico e l'autenticità di "Casa al Gianni", il nostro agriturismo nel cuore della campagna Toscana a 20 minuti da Siena. Dopo una recente ristrutturazione, i nostri alloggi sono pronti ad accoglierti con tutto il confort moderno senza perdere l'essenza della tradizione. Nell'Appartamento Olmo, ti aspettano letti completamente nuovi, promessa di sonni tranquilli e rigeneranti, nuova cucina e nuovo bagno.

Guest favourite
Farm stay in Campiglia D'orcia
4.94 out of 5 average rating, 470 reviews

Agriturismo Poggio Bicchieri ap. Poesia

Il nostro agriturismo è una finestra sulla val d'orcia, composto da 2 appartamenti con cucina, camera e bagno. Grande giardino attrezzato. Immerso nel silenzio, vicino a Pienza, Montalcino, Bagno Vignoni e le terme naturali di Bagno San Filippo. Per raggiungerci è molto semplice, l'ultimo km di strada è sterrata ma percorribile da tutti.

Popular amenities for Pienza family-friendly rentals

When is the best time to visit Pienza?

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Avg. price$238 NZD$240 NZD$285 NZD$270 NZD$293 NZD$263 NZD$290 NZD$295 NZD$292 NZD$270 NZD$251 NZD$245 NZD
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Quick stats about holiday rentals that are family-friendly in Pienza

  • Total holiday rentals

    Explore 20 holiday rentals in Pienza

  • Nightly prices starting at

    Pienza holiday rentals start at $142 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,270 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    20 of Pienza holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Pienza rentals

  • 4.9 Average rating

    Pienza stays are highly rated by guests—averaging 4.9 out of 5!

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