
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
Transformed from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, large equipped kitchen, large living room and a large private garden with parking, hot tub, patio with sofas, BBQ, fire pit and 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, between relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Da nonna Ornella - nest in Val d'Orcia
Spectacular views and relaxation guaranteed in this romantic studio in the heart of the Val d'Orcia, province of Siena, immersed in the beautiful Tuscany. Ideal for couples. It has a living area, equipped kitchen, bathroom, heating, courtyard, private parking and a large and panoramic garden with sun loungers and hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d'Orcia, Radicofani, Castiglione d'Orcia and Monte Amiata. Unforgettable!

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.

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.

Casa Dolce Toscana~Suite&View
CASA DOLCE TOSCANA đŒïž Hi! I'm Jolanta đ Welcome to our beloved Tuscan accommodation,with panoramic views,immersed in the hills of Tuscany. Anoasis of peace perfect for those who want to relax and live an authentic experience. Located a few kilometers from Siena and Florence,our accommodation combines rustic charm with all modern comforts. it is in the heart of the historic center of the famous village of Cetona,below the castle ,overlooking the valley and the scent of Tuscany.

The Terrace of Victory
La Terrazza di Vittoria is a delightful studio on one level surrounded by silence and greenery. It is located a few meters from the main house and just 2 km from CittĂ della Pieve. The large garden surrounding the house is a natural terrace overlooking Lake Trasimeno. It is enriched by a pergola equipped with a table and barbecue available for your meals in total relaxation. Inside, in a 40 sqm space, there is a double bed, a sofa bed, a bathroom and an equipped kitchen.

Apartment in a detached villa - Val d'Orcia
In a detached villa, a cozy Tuscan-style apartment recently and tastefully 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 panorama you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval fortress From 03/22/18, municipal tourist tax: âŹ1 per person from 12 years old

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.

Rosaspina - Poggio Alla Serra
Rosaspina is located in the open countryside a stone's throw from the historic center of the village of Cetona, on the slopes of the homonymous mountain, in the south of the Province of Siena. It is furnished with the typical taste of the country house with views of the village and the mountains.
Popular amenities for Pienza house rentals
House rentals with a pool

Italian Interior

Infinity pool in Chianti area

Charming estate with views

Explore Chianti from a Charming Stone House

Nada Home

Casa di Lyndall - Entire house with exclusive pool

Luxury Villa with a fantastic view

Gaiole in Chianti Poggio Casabianca
Weekly house rentals

Hidden gem in Tuscany

Casa Ora d"Oro - Panoramic Views

La Casetta di Alice - with panoramic terrace -

Family Forest - Pool in the Crete Senesi

Traditional stone house in Umbria.

Lovely home to dream

La Perla del Lago Holiday home on Lake Trasimeno

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

Apt. Elena - Villa Augusto Estate

Casale with pool -Ad Galli Cantum- Vesper

City Center Palazzo: 4 King BR 6 Bath and Garage

Country chic house in a village,private pool,wiFi

Dreamy Tuscan Vista Stay in Cozy Country Home

"Hortus Conclusus" House

Perfect Large Family Villa in Tuscany

Dimora del Vino
Quick stats about house rentals in Pienza

Nightly prices starting at
Pienza vacation rentals start at $140Â CAD per night before taxes and fees

Verified guest reviews
Over 60 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 guestsâaveraging 5 out of 5!
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- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Kite Beach Fiumara
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Tenuta Le Velette
- Terme Dei Papi
- Cala Di Forno
- Castiglion del Bosco Winery
- Marina di Grosseto beach
- Golf Club Toscana
- Santa Maria della Scala
- Pubblico Palace
- Cantina Stefanoni
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Madonna del Latte
- Podere Il Cocco
- Azienda Agricola Montefioralle Winery
- Poggio Talamonaccio




