
Holiday rentals in Pienza
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Quick stats about holiday rentals in Pienza

Total holiday rentals
Explore 80 holiday rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 3,260 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
70 of Pienza holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Pienza rentals

4.8 Average rating
Pienza stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated holiday rentals in Pienza
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Tuscan Villa with View forFamily&Friends
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!

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

The walnut tree view, Montepulciano
The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment

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.

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!

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

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.

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.
La Piazzetta -Accogliente open space nel centro storico di Montepulciano
Versati un bicchiere di vino e accomodati di fianco al caminetto di questo open space dalla calda atmosfera tipicamente toscana: travi in legno, pavimento in cotto, pareti in pietra. Poi esci e ammira il magnifico panorama sulla 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, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

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.

I Tramonti di Eramo, Montepulciano centro.
Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
Popular amenities for Pienza holiday rentals
Other great holiday rentals in Pienza

Agriturismo Fattoria La Parita

Mascagni Farmhouse in Val d'Orcia Pienza

a.d. 1237

Podere Pereti Vecchi | Stunning Val d'Orcia Views

Stuart White Tea Central Panoramic & Garden

Spacious Luxury Stay in Pienza | 3BR 3BA

Casa Bonari - un paradiso per gli occhi

Elegant farmhouse overlooking Pienza
When is the best time to visit Pienza?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 SGD | $148 SGD | $164 SGD | $159 SGD | $167 SGD | $163 SGD | $167 SGD | $181 SGD | $183 SGD | $170 SGD | $167 SGD | $165 SGD |
| 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 |
Frequently Asked Questions
What are the best places to stay in Pienza?
Stays in Pienza’s historic center place travelers near main squares, shops, and local markets, providing an authentic experience. Countryside accommodations around the town often feature views of the rolling hills.
What are the best things to do in Pienza with kids?
Families can explore cheese shops offering tastings, join countryside strolls, and visit local gardens or parks for outdoor play. Occasional art workshops and markets provide hands-on activities for children.
What are some of the best things to do in Pienza?
Explore the town's Renaissance architecture, wander through artisan shops, and sample regional cheese at local markets. Stroll the main square, visit centuries-old churches, and enjoy panoramic views over the Val d'Orcia.
How is the weather in Pienza?
Pienza has mild springs, warm summers around 60–89°F (16–32°C), and cool, wetter winters near 33–49°F (0–9°C). Light layers suit changing conditions, with rain more frequent in autumn and winter.
When is the best time to visit Pienza?
Late spring and early autumn are often recommended for visiting Pienza, with comfortable temperatures around 60–74°F (16–23°C) and fewer crowds. Mild weather makes it pleasant to explore medieval streets and scenic countryside.
What are the best places to visit in Pienza?
Palazzo Piccolomini, the Cathedral of Pienza, and Piazza Pio II are frequently suggested sites. Many visitors also explore the town's medieval walls and panoramic terraces over the Val d'Orcia.
What are some hiking trails in Pienza?
The countryside around Pienza has scenic walking paths through farm fields and olive groves, including routes into the Val d'Orcia. Trails often pass hilltop viewpoints and traditional hamlets.
What are some family activities we can do in Pienza?
Families can explore the town’s squares, visit interactive cheese shops, and stroll scenic rural paths. Local parks and workshops sometimes engage children in hands-on culinary or craft experiences.
What are some of the best day trip ideas from Pienza?
Nearby small towns, vineyards, and thermal baths are frequently suggested for day trips. Explore rural villages, historical sites, and countryside walking paths around the area.
Are there any pet friendly accommodations available in Pienza?
Many vacation rentals in Pienza welcome pets, especially in the countryside and select areas of the historic center. Confirm specific amenities and space for pets with the host before booking.
What are some local tips for visiting Pienza?
Early mornings are quieter for exploring town lanes and markets. Try seasonal Pecorino varieties and visit small local bakeries for unique breads and pastries.
What is Pienza known for?
Pienza is known for its Renaissance town design and cultural heritage, shaped by Pope Pius II. The area is also celebrated for Pecorino cheese and scenic views across the rolling hills of southern Tuscany.
What are the best hidden gems to explore in Pienza?
Discover small artisan studios tucked on side streets, or visit quiet chapels and viewpoints around the historic walls. Lesser-known gardens offer peaceful spots to relax and soak in the countryside.
What are the best foods to try in Pienza?
Pienza has Pecorino cheese, handmade pasta like pici, and rustic breads. Local specialties often include wild herbs, truffles, and Tuscan cured meats paired with regional wines.
What should I bring for a trip to Pienza?
Pack comfortable shoes for exploring cobbled streets, layers for changing weather, and a light jacket in cooler months. A reusable water bottle and sun protection are helpful for outdoor activities.
What is the nightlife in Pienza like?
Nightlife in Pienza is generally relaxed, with wine bars, casual cafes, and restaurants creating a mellow evening atmosphere. Locals and visitors unwind with regional wine and small plates in historic settings.
What are the most popular events or festivals in Pienza?
Pienza has the Fiera del Cacio, a festival celebrating Pecorino cheese, usually held around early September with tastings and local traditions. Religious festivals, seasonal markets, and craft fairs also bring people together in the town's main squares.
Are there family friendly vacation rentals in Pienza?
Pienza has family-friendly vacation rentals, including traditional apartments and countryside homes. Many stays feature spacious settings and welcoming amenities suitable for children.
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- Avignonesi Winery Fattoria Le Capezzine
- La Scarzuola
- Mount Amiata
- Palazzo Pubblico
- Siena Cathedral
- Vulci
- Antinori nel Chianti Classico
- Ugolino Golf Club
- Val di Chiana
- Terme San Filippo
- Valdichiana Outlet Village
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Riserva Naturale Diaccia Botrona
- Saturnia Thermal Park
- Things to do Pienza
- Things to do Siena
- Sports activities Siena
- Art and culture Siena
- Entertainment Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Entertainment Italy
- Food and drink Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy







