
House holiday rentals in Pienza
Find and book unique houses on Airbnb
Top-rated house rentals in Pienza
Guests agree: these houses are highly rated for location, cleanliness and more.

Casa Luigi Suite with exclusive pool
Come to this apartment: you will be welcomed by centuries of tranquility, and appreciate nature and relaxation. Carefully modernized (and with a swimming pool), this space embodies the roots of good Tuscan living – an equipped olive grove consisting of a pergola with a table and bathroom, a garden with a hammock and in the shade of pine and cypress trees, with chairs, deck chairs and a rocking chair, you can admire the rolling Chianti hills. Courtyard equipped with table and chairs. There is a beautiful elevated swimming pool with some games and a barbecue In addition to the farmhouse, the property includes an olive grove of about 1 hectare, in which equipped spaces have been created for complete relaxation. The Suite has a private entrance that leads directly to the upper floor of the farmhouse, allowing maximum privacy for guests. The farmhouse is part of a small old village inhabited by 4 very discreet and friendly family units. The suite's surface area is 90 square meters and consists of a dining room with kitchenette, large living room, double bedroom, bathroom with shower and a large attic (the door is 1.2 meters wide) with 3 single beds. A very bright environment and immersed in the complete tranquility of the countryside, it is equipped with air conditioning, satellite TV, and free 24-hour Wi-Fi. The owners provide the laundry area. Uncovered private parking. The owners are happy to welcome their guests and are available to resolve any issues. The small village is inhabited by three other very kind and discreet families, ready to help the guest. Tavarnelle is 25 km from Florence, 15 km from San Gimignano, 35 km from Siena. - Images of the exterior, swimming pool, garden and equipped olive grove will be visible soon. We kindly ask you to wait. The accommodation is about 5 km from the center of Tavarnelle. The historic center is equipped with all the services for the citizen and tourist: post office, police, municipality, emergency room, supermarket, trattorias, pizzerias, banks, etc. In addition, in the summer there are various musical events, small craft markets, and finally, every Thursday morning, the classic municipal market takes place. Places of interest (medieval villages) around Tavarnelle: San Donato in Poggio about 12 km. Barberino Val d'Elsa 6 km. Distances from art cities: Tavarnelle - Florence about 25 km Tavarnelle - San Gimignano/Monteriggioni about 20 km Tavarnelle - Siena about 35 km. In the organized outdoor spaces there is an ABOVE GROUND pool, the dimensions are: 10 meters X 5 meters, with a depth of 1.20 meters. A bathroom with shower completes the pool area. In the courtyard, guests have a nice table with barbecue. The entire olive grove area is at their disposal with maximum privacy. The owners, at the guest's request, can book hiking tours or wine-testing tours with the help of professionals. The price of any tour booking is not included in the price of the stay. The small village was once a military fortress, then a parish church or place of worship and from the beginning of the 20th century inhabited by farmers. Today it is inhabited by four very nice and discreet families ready to help the guest. Florence is 15.5 miles away and Siena is 21.7 miles away

Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, 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 seeking 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!

Apartment in a detached villa - Val d'Orcia
In a detached villa, a cozy Tuscan-style apartment, recently and tastefully renovated, located in an area rich in history. Located just a few kilometers from cities of art and on the Via Francigena, the apartment can serve as a base for nature trails or food and wine tours. From a lovely terrace overlooking the panorama, you can enjoy your meals, admire the sunset, and gaze at the majestic and magnificent medieval fortress. .As of March 22, 2018, a municipal tourist tax of €2 per person applies. See additional notes.

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

Sunset on Chianti Classico
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 | Panoramic Suites & Views
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.

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.

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.*
Popular amenities for house rentals in Pienza
House rentals with a pool

Italian Internal

Charming estate with views. A/C in the bedrooms

Il nido del Rondone

Nada Home

Borgo Ripostena – No. 8 Casa Vecchia

Country House in the Crete Senesi

House Rigomagno Siena

PoggiodoroLoft, Tuscan dream e relax
Weekly house rentals

Family Forest - Pool in the Crete Senesi

Casa di Vico, just a short walk from the center of Pienza

[Little Escape] 4 Beds + Private Panoramic Pool

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

Domus Antiqua
Private house rentals

Hidden gem in Tuscany

Private Cottage with Plunge Pool in Tuscan Estate

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Cozy Tuscan Country House with Fantastic View

Wine House

Poggiolo

Villa Le Rughe • Private terrace & 300Mb WiFi

Montepulciano Old Town
Quick stats about house rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at $115 SGD 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
- Palazzo Pubblico
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- La Scarzuola
- Santa Maria della Scala
- Antinori nel Chianti Classico
- Saturnia Thermal Park
- Ugolino Golf Club
- Terme San Filippo
- Mount Amiata
- The Riserva Naturale Della Laguna Di Orbetello
- Valdichiana Outlet Village
- Abbey of Monte Oliveto Maggiore
- Abbey of Sant'Antimo
- Vulci
- San Gimignano 1300





