
Holiday houses in Pienza
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Top-rated holiday rentals in Pienza
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Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

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!

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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.

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.

Casa Dolce Toscana | Panoramic Suite with View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

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

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.

The Loggia
Country house located in Radda, the heart of the Chianti, within walking distance from the historical center and other services such as; Coffee shops, Post Office,grocery stores and restaurants. The house is composed of a full equipped kitchen, living room with a sofa bed, bedroom, loggia and bathroom. The property is surrounded by a garden and there is a nice wooden table in the garden to eat in an open space and another lounge spot to enjoy the magnificent landscape.

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?

Casa Crociani - Amazing Pool & Free Parking
Just 4.7 km from Montepulciano (7 minutes by car), this house is located in a quiet position surrounded by greenery, with a splendid view of the Tuscan hills. The property is equipped with all the necessary amenities to ensure a pleasant stay, perfect for relaxing weekends or vacations. You can relax on the private patio, in the outdoor gardens, or spend unforgettable moments by the pool, enjoying the peace and beauty of the surrounding landscape.

I Tramonti di Eramo, Montepulciano city center.
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.
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When is the best time to visit Pienza?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $147 AUD | $147 AUD | $152 AUD | $175 AUD | $184 AUD | $179 AUD | $184 AUD | $199 AUD | $202 AUD | $188 AUD | $184 AUD | $182 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 |
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.
Quick stats about holiday rentals in Pienza

Total holiday rentals
Explore 70 holiday rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at $114 AUD per night before taxes and fees

Verified guest reviews
Over 2,920 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

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

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

4.9 Average rating
Pienza stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Lake Trasimeno
- Del Chianti
- Lake Bolsena
- Cala Violina
- Cascate del Mulino
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Terme Dei Papi
- Palazzo Pubblico
- Santa Maria della Scala
- Ugolino Golf Club
- Rocca Maggiore
- Siena Cathedral
- Castello di Verrazzano
- Antinori nel Chianti Classico
- Abbey of Monte Oliveto Maggiore
- Riserva Naturale Diaccia Botrona
- Parco Regionale Della Maremma
- Val di Chiana
- Cathedral of San Lorenzo
- Pozzo di San Patrizio
- Saturnia Thermal Park
- Abbey of Sant'Antimo
- Girifalco Fortress




