
House vacation rentals in Pienza
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Top-rated house rentals in Pienza
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Il Focolare - Superior Tuscany Apartment
The "Il Focolare" apartment 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 with cypresses, rolling hills as far as the eye can see and winding white roads. Newly renovated (2019), it perfectly blends its historical soul with modern furnishings, giving the environment personality and charm, while the fireplace in the bedroom adds that extra touch of romance. Total 52 sqm

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

Montalcino Townhouse with Private Garden & Spa
A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

The Chianti Classico Sunset
Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Casa Dolce Toscana ~Suite&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 03/22/18, a municipal accommodation tax of €2 per person from the age of 12 will be charged.

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.

Cottage surrounded by nature
"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.
Popular amenities for Pienza house rentals
House rentals with a pool

Infinity pool in Chianti area

Vineyards Paradise

Charming estate with views. A/C in the bedrooms

Il nido del Rondone

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

The Owl: view, pool and garden

Country House in the Crete Senesi
Weekly house rentals

Hidden gem in Tuscany

La Casetta di Alice - with panoramic terrace -

Lovely home to dream

Casa Al Poggio & Chianti view

Casa di Mela

Dreamy Tuscan Vista Stay in Cozy Country Home

Country chic house in a village,private pool,wiFi

Pienza Center - Stylish Apt, 6 Guests, A/C & WiFi
Private house rentals

Family Forest - Pool in the Crete Senesi

The House of Olives

Cozy Artist Retreat in the heart of Sorano

Casa Letizia: Val d'Orcia, Thermal Baths and Mount Amiata

Stunning loft in Montalcino.

The Two of Us Vacation in Fortino d'Amore

"Hortus Conclusus" House

Tosco Suite "Solis"
Quick stats about house rentals in Pienza

Nightly prices starting at
Pienza vacation rentals start at G$18,838 GYD per night before taxes and fees

Verified guest reviews
Over 100 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!
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- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Cala Violina
- Cascate del Mulino
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Terme Dei Papi
- Basilica of St Francis
- Palazzo Pubblico
- Santa Maria della Scala
- Antinori nel Chianti Classico
- Rocca Maggiore
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Riserva Naturale Diaccia Botrona
- Saturnia Thermal Park
- Pozzo di San Patrizio
- Castello di Verrazzano
- Vulci
- Parco Regionale Della Maremma
- Terme San Filippo
- Val di Chiana
- Abbazia di San Galgano




