
House holiday rentals in Pienza
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Quick stats about house rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at $126 AUD per night before taxes and fees

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Over 110 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pienza rentals

5 Average rating
Pienza stays are highly rated by guests—averaging 5 out of 5!
Top-rated house rentals in Pienza
Guests agree: These houses are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

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.

Montepulciano Historic Center
nice and comfortable apartment in the old town of Montepulciano Placed in the Historical Centre, just a few steps to the most beautiful and oldest wine cellar in Montepulciano (Cantina del Redi dè Ricci) an amazing sixteenth-century structure, great-looking with its huge wine barrels. The apartment is in a perfect position: just a few minutes walk from the main square of the town, Piazza Grande(where, every summer, there are theatre and music events) but at the same time is a quiet district.

Da nonna Ornella - nest in Val d'Orcia
Vista spettacolare e relax assicurato in questo romantico monolocale nel cuore della Val d’Orcia, provincia di Siena, immerso nella splendida Toscana. Ideale per coppie. Dispone di zona living, cucina accessoriata, bagno, riscaldamento, resede, parcheggio privato e un grande e panoramico giardino con lettini e amaca. Vicino a mete iconiche: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d’Orcia, Radicofani, Castiglione d’Orcia e Monte Amiata. Indimenticabile

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.

Apartment in a detached villa - Val d'Orcia
In a cozy independent villa in Tuscan style apartment recently and finely renovated and located in a land rich in history. A few kilometers from the city of art and on Via Francigena, the apartment can be a base for nature or food and wine trails. From a beautiful terrace overlooking the view you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval Rocca From 22/03/18, a municipal tourist tax of €2 per person will be charged. See additional notes

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

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.

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.

Jenny's Barn
The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

La casa nel Borgo - Superior Tuscany Apartment
La Casa Nel Borgo is located in the small medieval village of Monticchiello, inside the historic center, between the ancient walls, immersed in the classic and enchanting landscapes of Tuscany. Newly renovated, it perfectly blends its historical soul with modern decor, giving the environment personality and charm. The terrace with a view is equipped. NOTE: *Only one room will be available for 2 people, unless explicitly requested.*
Popular amenities for Pienza house rentals
House rentals with a pool

Dimora Il Convento

Casa Lucy

Cottage surrounded by nature

Family Forest - Pool in the Crete Senesi

Private Cottage with Plunge Pool in Tuscan Estate

Casa Olivo | Il Fossaccio Farm

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House
Weekly house rentals

Hidden gem in Tuscany

Lovely home to dream

Borgo71 - In the Heart of the Val d'Orcia

Dream villa in Chianti with panoramic garden

City Center Palazzo: 4 King BR 6 Bath and Garage

Stunning loft in Montalcino.

Domus Antiqua

Wine House
Private house rentals

"Villa Emma" Guest House with Garden

S.Ilaria - Private pool Villa with 2 bedrooms

Little Corticellitta in Tuscany

Enjoy Amazing View in Tuscany in Our Country House

Casa Ilda A/C, Wi-Fi Private parking

Poggiolo

Villa Le Rughe • Private terrace & WiFi 300Mb

Private 16th century farmhouse
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cala Violina
- Cascate del Mulino
- Basilica of St Francis
- Avignonesi Winery Fattoria Le Capezzine
- Terme Dei Papi
- Palazzo Pubblico
- Santa Maria della Scala
- Ugolino Golf Club
- Rocca Maggiore
- Antinori nel Chianti Classico
- Parco Regionale Della Maremma
- Siena Cathedral
- Abbey of Monte Oliveto Maggiore
- La Scarzuola
- Val di Chiana
- Riserva Naturale Diaccia Botrona
- Cathedral of San Lorenzo
- Terme San Filippo
- Saturnia Thermal Park
- Abbey of Sant'Antimo
- Giardini del Frontone




