
House holiday rentals in Pienza
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Top-rated house rentals in Pienza
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Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available
ValueLocationWi-Fi

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!
LocationFamilyNearby

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.
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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
LocationFamilyLaundry

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the Chianti Classico region, surrounded by the vineyards and olive groves of the beautiful Tuscan hills, on the estate of a historic 16th-century villa, then come to our barn!! It has a dominant position with an amazing view, where you can enjoy breathtaking sunsets. The complete independence of the house, the welcoming garden and the large loggia allow you to enjoy your stay in total tranquillity. Our reviews are your best guarantee.
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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.
LocationFamilyBreakfast

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
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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.
LocationFamilyShared spaces

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.
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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.
LocationFamilyBarbecue

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.*
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Casa Belmonte
Just renovated elegant house in the historic center of Montepulciano, just 6 minutes from Piazza Grande and 4 minutes from Porta al Prato. Composed on the ground floor by a large open space with kitchenette while on the first floor there are two double bedrooms and two bathrooms. It is equipped with dishwasher, microwave oven, coffee maker, TV and free use of Wi-Fi.
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Popular amenities for Pienza house rentals
House rentals with a pool

Cottage surrounded by nature
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Infinity pool in Chianti area
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Podere Scorno country house with swimming pool
LocationComfortParking

Italian Internal
LocationValueBathroom

SuiteLouise.pool, Hot Tub,homeGym & private Garden
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Il nido del Rondone
ValueFamilyComfort

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
LocationValueDecor

Country House in the Crete Senesi
ValueFamilyBiking
Weekly house rentals

Montepulciano Historic Center
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Love in Chianti
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Lovely home to dream
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City Center Palazzo: 4 King BR 6 Bath and Garage
ValueLocationWalkability

Spacious Luxury Stay in Pienza | 3BR 3BA
LocationFamilyWalkability

At the Sassone Holiday Home, Val d'Orcia, Tuscany
LocationFamilyHeating

Amazing Cott. in the heart of Siena
FamilyLocationBiking

the birds view
FamilyValueAmenities
Private house rentals

Hidden gem in Tuscany
FamilyLocationAccess

"Villa Emma" Guest House with Garden
FamilyLocationQuiet

Family Forest - Pool in the Crete Senesi
LocationFamilyQuiet

Open Space Piscina e Giardino
LocationPoolAmenities

Private Cottage with Plunge Pool in Tuscan Estate
LocationGetting aroundComfort

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

Relaxing Country Home in Tuscany with View
LocationFamilyKitchen

Stunning loft in Montalcino.
LocationFamilyView
Quick stats about house rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at $128 AUD 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
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Centro Storico Orvieto
- Terme Dei Papi
- Cascate del Mulino
- La Scarzuola
- Avignonesi Winery Fattoria Le Capezzine
- Siena Cathedral
- Palazzo Pubblico
- Terme San Filippo
- Antinori nel Chianti Classico
- Ugolino Golf Club
- Vulci
- Mount Amiata
- Val di Chiana
- Valdichiana Outlet Village
- Abbey of Sant'Antimo
- Saturnia Thermal Park
- Riserva Naturale Diaccia Botrona
- Abbey of Monte Oliveto Maggiore





