
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 $125 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

Infinity view
Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

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.

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.

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.*

"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.
Popular amenities for Pienza house rentals
House rentals with a pool

Cozy country house Podere Scorno with pool Tuscany

Cottage surrounded by nature

Casa Lucy

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House

Luxury Villa with a fantastic view

Casa Luigi Suite with exclusive pool

House Rigomagno Siena
Weekly house rentals

Family Forest - Pool in the Crete Senesi

Casa di Vico, a stone's throw from the centre of Pienza

Casa Olivo | Il Fossaccio Farm

Lovely home to dream

City Center Palazzo: 4 King BR 6 Bath and Garage

Stunning loft in Montalcino.

Country chic house in a village,private pool,wiFi

Wine House
Private house rentals

Hidden gem in Tuscany

"Villa Emma" Guest House with Garden

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Borgo71 - In the Heart of the Val d'Orcia

Casa Ilda A/C, Wi-Fi Private parking

Domus Antiqua

Poggiolo

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





