
House vacation rentals in Pienza
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Top-rated house rentals in Pienza
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Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, 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, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this 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.

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 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.

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 the Via Francigena, the apartment can be a base for nature or food and wine tours. From a beautiful terrace overlooking the view you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval Rocca From 03/22/18, the municipal accommodation tax is €2 per person. See additional notes.

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.

House of the Jujube
Facing the old medieval walls of this ancient city, the location of the house will make you feel relaxed thanks to the peacefulness of the countryside and the vitality of the centre. Bathed in the gorgeous sunlight from sunrise to sunset, Casa delle Giuggiole will give you a sensation of lightness and freedom. Look through any one of the many windows and you can admire both the astonishing landscape of the Val d'Orcia and the typical Tuscan roofs.

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.*

Casa Al Poggio & Chianti view
Casa al Poggio is a typical country house of Chianti area is spread in 145 square meters on two floors, the ground floor is a large living area, with kitchen and sofa ,fireplace ,up stairs there is 2 large double bedrooms and a sofa bed in the middle open room , always setable as 2 singles or a double bed bed and a relaxing bathroom with shower and bath with Chianti view.

"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

Podere Scorno country house with swimming pool

Cottage surrounded by nature

Italian Internal

Infinity pool in Chianti area

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Il nido del Rondone

Borgo Ripostena – No. 8 Casa Vecchia

Nada Home
Weekly house rentals

Family Forest - Pool in the Crete Senesi

Casa di Vico, within walking distance of the center of Pienza

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Lovely home to dream

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

Hidden gem in Tuscany

Luxury Villa with Private Pool

Private Cottage with Plunge Pool in Tuscan Estate

Casa Ilda A/C, Wi-Fi Private parking

Authentic Tuscany Experience in Our Country House

Poggiolo

Villa Le Rughe • Private terrace & 300Mb WiFi
Quick stats about house rentals in Pienza

Nightly prices starting at
Pienza vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
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!
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Del Chianti
- Centro Storico Orvieto
- Basilica of St Francis
- Terme Dei Papi
- La Scarzuola
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- Palazzo Pubblico
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Casa Vasari
- Santa Maria della Scala
- Terme San Filippo
- Mount Amiata
- Saturnia Thermal Park
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Vulci
- Val di Chiana





