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Vacation rentals in Pienza

Find and book unique accommodations on Airbnb

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 G$16,738 GYD 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
Villa in Montepulciano
4.97 out of 5 average rating, 126 reviews

Wine Experience Villa in Montepulciano

🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

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
4.97 out of 5 average rating, 187 reviews

Casa Bonari - un paradiso per gli occhi

Casa Bonari è un appartamento indipendente, non condiviso, su un unico livello all'interno di una villa ai piedi di Monticchiello. E' composto da 3 camere da letto, 2 bagni, cucina full optioned e salotto. Le stanze sono 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 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
4.97 out of 5 average rating, 250 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 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
4.98 out of 5 average rating, 165 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 or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

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
4.93 out of 5 average rating, 334 reviews

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

Top guest favorite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5.0 out of 5 average rating, 162 reviews

Casa rurale toscana in Mascagni Farmhouse 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?

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
4.98 out of 5 average rating, 183 reviews

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.

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
4.99 out of 5 average rating, 232 reviews

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.

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
4.98 out of 5 average rating, 182 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

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
4.96 out of 5 average rating, 137 reviews

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.

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
4.97 out of 5 average rating, 100 reviews

Spacious Luxury Stay in Pienza | 3BR 3BA

Scopri un rifugio elegante, spazioso e autentico nel cuore di Pienza, gioiello rinascimentale Patrimonio UNESCO. Con 3 camere matrimoniali, 3 bagni, ampia zona living, cucina attrezzata, A/C e Wi-Fi, questa casa è perfetta per famiglie o amici che desiderano vivere la Toscana più iconica tra vicoli storici, sapori unici e panorami indimenticabili sulla Val d’Orcia, con tutto il comfort di una dimora davvero speciale.

Top guest favorite
Farm stay in Campiglia D'orcia
4.95 out of 5 average rating, 577 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 vacation rentals

When is the best time to visit Pienza?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,316 GYDG$24,060 GYDG$26,571 GYDG$29,709 GYDG$31,383 GYDG$29,082 GYDG$26,989 GYDG$29,291 GYDG$29,709 GYDG$27,617 GYDG$26,989 GYDG$26,780 GYD
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.

Destinations to explore