
Holiday houses in Pienza
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Top-rated holiday rentals in Pienza
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Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Agriturismo Fattoria La Parita
Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

Amazing Tuscany Villa, FREE parking
Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Casa Dolce Toscana~Suite&View
CASA DOLCE TOSCANA 🖼️ Ciao! Sono Jolanta 😊 Benvenuti nel nostro amato alloggio toscano ,con vista panoramica,immerso nelle colline della Toscana.Un’oasi di pace perfetta per chi desidera rilassarsi e vivere un’esperienza autentica. Situato a pochi chilometri da Siena e Firenze,il nostro alloggio combina il fascino rustico con tutti i comfort moderni. si trova nel cuore del centro storico del famoso borgo di Cetona,sottostante al castello ,con vista sulla valle e il profumo della Toscana.

Luxurious Medieval Tower & Private Concierge
It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Casa Bonari - un paradiso per gli occhi
Casa Bonari è un appartamento indipendente su un unico livello all'interno di una villa ai piedi di Monticchiello. E' composto da 3 camere da letto, 2 bagni, cucina attrezzata e salotto. Le stanze sono luminose e arredate in stile toscano, con vecchi mobili di famiglia ristrutturati uniti ad elementi contemporanei. La cucina è completamente attrezzata e l'appartamento circondato su ogni lato da un grande giardino, così che tutte le stanze vantano un bellissimo panorama sulla campagna.
La Piazzetta -Accogliente open space nel centro storico di Montepulciano
Versati un bicchiere di vino e accomodati di fianco al caminetto di questo open space dalla calda atmosfera tipicamente toscana: travi in legno, pavimento in cotto, pareti in pietra. Poi esci e ammira il magnifico panorama sulla Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

Verde - I prati in Toscana
Appartamento composto da 1 camera matrimoniale , cucina attrezzata, ampio soggiorno e bagno Tv, BBq, ( mettiamo a disposizione la lavatrice dalle 9 alle 20 che è nella nostra lavanderia a chi ne fa richiesta ) . Consigliamo l'auto in quanto abitiamo in campagna, sia per essere indipendenti , sia per visitare la magnifica toscana Ti piacerá l'ambiente esterno perché é magico di giorno e di notte Parcheggio e wifi gratis Posizione strategica per visitare la Toscana e l'Umbria.

Casale Santa Barbara - Exclusive Apartment
At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

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.
Popular amenities for Pienza holiday rentals
Other great holiday rentals in Pienza

Podere Pereti Nuovi-modern Tuscan Villa

Agriturismo Via della Stella | Casa le Rose

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

Appartamento Mimosa - Poggio al Vento

Cipressini 2 - piscina e vista mozzafiato

Gli sterpi

Room in agriturismo Montepulciano e Cortona

Pociano.1863 The Horizon Suite
When is the best time to visit Pienza?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $181 NZD | $181 NZD | $189 NZD | $217 NZD | $227 NZD | $222 NZD | $227 NZD | $247 NZD | $250 NZD | $199 NZD | $194 NZD | $192 NZD |
| 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 |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Pienza?
Four-legged friends are welcome in Pienza. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Pienza?
Yes! Work meets play with ease at over 20 vacation rentals in Pienza featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Pienza have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Pienza. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Pienza have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Pienza. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in bed and breakfast rentals in Pienza?
Experience the best of Pienza with our bed and breakfast rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly apartment rentals in Pienza?
Pienza has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Pienza

Total holiday rentals
Explore 70 holiday rentals in Pienza

Nightly prices starting at
Pienza holiday rentals start at $141 NZD per night before taxes and fees

Verified guest reviews
Over 2,730 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
70 of Pienza holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace 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
- Cala Violina
- Kite Beach Fiumara
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Cala Di Forno
- Basilica of St Francis
- Terme Dei Papi
- Castiglion del Bosco Winery
- Golf Club Toscana
- Marina di Grosseto beach
- 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
- Cantina Contucci




