
Apartment holiday rentals in Pienza
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Top-rated apartment rentals in Pienza
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Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Stuart Black Tea Amazing View & Super Central
This apartment is in a prime central location and enhanced by an abundance of natural light and awe-inspiring panoramic vistas. It features one double bedroom, a panoramic living room, a bathroom with shower, and a spacious kitchen. Its advantageous proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Additionally, guests will have access to a backyard garden, creating an ideal setting for savouring a glass of wine

Montepulciano Historic Center
Nice 60-square-meter apartment located on the main street of the town. It is located on the second and top floor of a historic building. The entrance is located on the main street of the town while the windows face the outside of the walls offering a breathtaking view. The apartment consists of: an entrance, a living room with a double sofa bed, a bedroom, a kitchen, and a bathroom with a roof window. It is equipped with a microwave, large oven, dishwasher, washing machine and wifi.

"L'Ovile" Apartment with a view of Val d'Orcia
In the countryside, along the panoramic road that leads from Pienza to Monticchiello, 2 km from Pienza, large studio divided into sleeping area, with double and single bed, living-dining area, kitchenette, bathroom. Veranda for outdoor dining and relaxation. Panoramic view of Val d'Orcia and its villages. A few kilometers from Montepulciano and Montalcino, and the Bagno Vignoni hot springs. From June to September PRIVATE SWIMMING POOL There is NO breakfast service

Villa di Geggiano - Perellino Suite
The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Resort Panoramic view - Free parking
Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

Casa Bonari - a paradise for the eyes
Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

I Tramonti di Eramo, Montepulciano city center.
Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

La Violetta di San Quirico, Historic Center.
Welcome to the heart of Tuscany, in San Quirico d'Orcia, where your stay will be an unforgettable experience in our apartment, offering the perfect combination of comfort and authentic Tuscan beauty. You'll enjoy the apartment's true magic as you look out the windows and be captivated by the 360-degree views of the majestic Val d'Orcia, its hills, vineyards, olive groves, and rooftops.

Comfortable and quiet in Pienza
Small but comfortable apartment located in a private courtyard a few dozen meters from the main door of Pienza. Completely independent, with terrace, equipped kitchen, and Wi-Fi. I remind those who use public transport that on Sundays there are no buses, only taxi service. I remind those who use public transport that on Sundays there are no buses, only taxis.

Romantic Tower's dating 1200
The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves
Pick figs and rosemary in secluded, extensive gardens and soak up the peace and quiet of this beautiful rural setting with spectacular panoramic views. Whitewashed walls, terracotta-tiled floors, and ceiling beams reflect the space's rich history.
Popular amenities for Pienza apartment rentals
Weekly apartment rentals

Borgo Iesolana Suite with terrace

Stylish Apartment with View, Private Terrace A/C

Casa Tórta - comfort room

Live Like a Local & Private Concierge Service

Via del Bacio Uno (literally Kiss Street One)

Poggio ai Gelsi, Ginestra Lodge

PoliFlora Panorama

Casa Evelina - Incredible View, Central Location
Private apartment rentals

Podere Ferranino #Fra Angelico Townhouse

Artistic Pienza | Breathtaking Val d'Orcia View

The Elegant Country Cottage 2 seats | 70Mb Wi-Fi

Girasole Apartment | Poggio Salto

Mimosa Apartment - Poggio al Vento

Mery's House: elegant apartment

WiFiFiber LargeApartment with view inMontepulciano

Apartment in Pienza's historic center
Apartment rentals with a hot tub

Casale La Cedrina (Il Melograno)

Romantic farmhouse, garden apartment with panorama

suite with Jacuzzi tub

San Giovanni in Poggio, Crepuscolo apartment 60 sqm

Charm Suite with swimming pool

Domus Nannini - L'Angolo di Paradiso Spa (Spa)

Charming House in Montepulciano

Luxury frescoed apartment in the historical center
When is the best time to visit Pienza?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £76 | £82 | £79 | £93 | £100 | £96 | £96 | £96 | £107 | £102 | £99 | £95 |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Quick stats about flat rentals in Pienza

Total holiday rentals
Explore 30 holiday rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 1,730 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Pienza holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pienza rentals

4.9 Average rating
Pienza stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- 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




