
Vacation rentals in Pienza
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Top-rated vacation rentals in Pienza
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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

Mascagni Farmhouse in Val d'Orcia Pienza
Risali le iconiche colline toscane fino a Mascagni Organic Farm, un'azienda biologica dove ti aspetta la tua nuova casa: un fienile del 1500 finemente ristrutturato immerso tra olivi e campi di grano. Rilassati prendendo una tazza di tè, raccogli rosmarini e lavande nel giardino con vista mozzafiato sulla Val d'Orcia. Riscopri la tua vera natura tra i campi incontaminati e gli olivi: qui le passeggiate e i giri in bici non hanno confini! Pronto a creare ricordi che dureranno tutta la vita?

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.

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.

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.

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.

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.

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

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.

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 vacation rentals
Other great vacation rentals in Pienza

Affitti Brevi Siena - The heart of Tuscany

Romantic Tuscan Holiday House

Tuscan villa in the heart of the Val d'Orcia

Terra Antica Suite & Ville - Cervognano

Borgo Iesolana Country Retreat Suite with terrace

Cipressini 2 - piscina e vista mozzafiato

Poggio ai Gelsi, Lodge Ginestra

the birds view
When is the best time to visit Pienza?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,543 GYD | G$21,543 GYD | G$22,380 GYD | G$25,727 GYD | G$26,981 GYD | G$26,354 GYD | G$26,981 GYD | G$29,282 GYD | G$29,701 GYD | G$27,609 GYD | G$26,981 GYD | G$26,772 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 |
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 vacation rentals in Pienza

Total vacation rentals
Explore 70 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 2,920 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
70 of Pienza vacation 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!
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