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Vacation rentals in Pienza

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Quick stats about vacation rentals in Pienza

  • Total vacation rentals

    Explore 80 vacation rentals in Pienza

  • Nightly prices starting at

    Pienza vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 3,260 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

    30 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

  • 4.8 Average rating

    Pienza stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Pienza

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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.

FamilyLocationDecor

4.97 out of 5 average rating, 252 reviews
Top guest favorite
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

Discover an elegant, spacious, and authentic retreat in the heart of Pienza, a Renaissance gem and a UNESCO World Heritage Site. Featuring 3 double bedrooms, 3 bathrooms, a large living area, a fully equipped kitchen, air conditioning, and Wi-Fi, this home is perfect for families or groups of friends who want to experience the most iconic side of Tuscany, with its historic alleyways, unique flavors, and unforgettable views of the Val d’Orcia, all with the comfort of a truly special residence.

FamilyLocationHospitality

4.97 out of 5 average rating, 102 reviews
Top guest favorite
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

ValueLocationTV

4.98 out of 5 average rating, 165 reviews
Top guest favorite
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 with a 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.

FamilyValueAir conditioning

4.98 out of 5 average rating, 188 reviews
Top guest favorite
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

LocationFamilyBreakfast

4.92 out of 5 average rating, 338 reviews
Top guest favorite
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.

ValueLocationAmenities

4.94 out of 5 average rating, 109 reviews
Top guest favorite
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.

LocationFamilySolo travel

4.99 out of 5 average rating, 233 reviews
Guest favorite
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 - a paradise for the eyes

Casa Bonari is an independent, non-shared apartment on one level within a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, a fully equipped kitchen, and a living room. The rooms are furnished in Tuscan style, with restored antique family furniture combined with contemporary elements. The kitchen is fully equipped, and the apartment is surrounded on all sides by a large garden, so all the rooms offer a beautiful view of the countryside.

FamilyValueSleep quality

4.97 out of 5 average rating, 187 reviews
Top guest favorite
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.
Vacation 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.

FamilyValueLong stay

4.96 out of 5 average rating, 139 reviews
Top guest favorite
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

Spedaletto Castle, Val d'Orcia, Pienza

The Castello di Spedaletto farmhouse is located in the building that once housed the granary of the ancient medieval castle and has been recently renovated in perfect balance between modernity and tradition: stone, bricks, exposed beams blend with the characteristic crystal and wrought iron staircase. The farmhouse consists of 5 double bedrooms with bathrooms and 2 apartments. Come, See, Live...

FamilyValueView

4.97 out of 5 average rating, 185 reviews
Top guest favorite
Farm stay in Campiglia D'orcia

Poggio Bicchieri Holiday Farm - Poesia Apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large, well-equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

LocationValueHot tub

4.95 out of 5 average rating, 580 reviews
Top guest favorite
The aerial view captures the historic structure nestled among rolling green hills, framed by tall trees. The stone walls reflect medieval architecture, while a terrace offers an inviting space below. The surrounding landscape showcases farms and cypress trees against a clear blue sky.
Home in Monticchiello

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

ValueLocationBathroom

4.98 out of 5 average rating, 225 reviews

Popular amenities for Pienza vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Other great vacation rentals in Pienza

Top guest favorite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

ValueFamilyHeating

4.97 out of 5 average rating, 126 reviews
Top guest favorite
A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.
Villa in Monticchiello

Villa unesco heritage, Jacuzzi & garden. BB Daria

ValueLocationIndoor spaces

4.98 out of 5 average rating, 183 reviews
Top guest favorite
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

FamilyValueAccuracy

5.0 out of 5 average rating, 116 reviews
Top guest favorite
A rolling landscape showcases neat rows of lush green vineyards under a softly lit sky. A charming village, featuring a prominent clock tower, is nestled among the trees and hills in the background. The tranquil atmosphere highlights the area's natural beauty.
Apartment in San Gusmè

Beautiful medieval village!!!

ValueFamilyGetting around

4.99 out of 5 average rating, 476 reviews
Guest favorite
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Apartment in Montepulciano

I Tramonti di Eramo, Montepulciano centro.

FamilyLocationLayout

4.91 out of 5 average rating, 310 reviews
Top guest favorite
An outdoor terrace is presented with a modern seating arrangement featuring two white cushioned chairs and a matching sofa surrounding a dark coffee table. The view captures the rooftops of Montepulciano, complemented by a clear blue sky and distant hills.
Apartment in Montepulciano

Dimora dell'Erbe - Rooftop Apartment

LocationFamilySleep quality

5.0 out of 5 average rating, 124 reviews
Top guest favorite
A rustic dining area features a spacious table set with plates and glassware, surrounded by wooden chairs. Exposed beams highlight the ceiling, while a soft lamp provides gentle illumination. A glimpse of the outside view can be seen through the window, enhancing the inviting atmosphere.
Apartment in Montepulciano

Tuscany on the terrace, downtown Montepulciano

FamilyLocationGetting around

4.91 out of 5 average rating, 239 reviews
Top guest favorite
A rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.
Farm stay in San Quirico d'Orcia

Podere Pereti Nuovi – Modern Tuscan Villa

ValueLocationWalkability

4.98 out of 5 average rating, 116 reviews

When is the best time to visit Pienza?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 444ﺩ.ﺇ 422ﺩ.ﺇ 466ﺩ.ﺇ 521ﺩ.ﺇ 551ﺩ.ﺇ 510ﺩ.ﺇ 474ﺩ.ﺇ 514ﺩ.ﺇ 521ﺩ.ﺇ 485ﺩ.ﺇ 474ﺩ.ﺇ 470
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°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.

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