
Holiday houses in Pienza
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Top-rated holiday rentals in Pienza
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Pienza holiday rentals
Other great holiday rentals in Pienza
Top Guest favourite

Condo in Torrenieri
4.97 out of 5 average rating, 242 reviews[9 minutes from Montalcino] Elegant House Mafalda
SandiipRating, 5 stars5 days ago
Excellent location in the heart of Val d Orcia. Quiet beautiful restaurants/shops and supermarkets nearby too - free parking across street and very clean rooms. excellent place to stay
Top Guest favourite

Apartment in Sinalunga
4.99 out of 5 average rating, 275 reviewsResort Panoramic view - Free parking
EnricoRating, 5 stars5 days ago
Charming stay, room and patio with a view that is unparalleled in beauty and tranquility. Beautiful room, well-stocked, everything extremely well cared for in detail by a person - Elena, although we did not have the opportunity to meet - who puts love into providing an experience that is absolutely to be repeated. The common areas are also extremely well-kept and comfortable.
Top Guest favourite

Condo in Montalcino
4.99 out of 5 average rating, 114 reviews"Landscape Notes" Suite
LaurenRating, 5 stars2 weeks ago
Everything was wonderful! Beautiful view from terrace! Fulvia was very helpful as well!
Guest favourite

Apartment in Montepulciano
4.94 out of 5 average rating, 196 reviewsI Tramonti di Eramo, Montepulciano city center.
SeungheeRating, 5 stars3 days ago
The picture of the sunset view from the balcony on the description attracted me, but I was wondering how much the expectation will be met. The actual view even surpassed the expectation. The stunning view is unforgettable. Everything in the house was tidy, cosy and lovely. The small town of Montepulciano was like something in a fairy tale, beautiful and peaceful.
Guest favourite

Condo in Montepulciano
4.92 out of 5 average rating, 127 reviews"Dimora Valinda" Montepulciano Piazza Grande +A/C
CassiRating, 5 stars1 week ago
Maria’s place was beautiful and exactly as described! It was bigger than expected and had a cute balcony we really enjoyed spending late afternoons relaxing! We had a great time in Montepulciano, it was relaxing and slow paced after a busy few weeks before ☺️ Maria provided local recommendations and was always responsive. If you’re thinking of booking here I highly recommend!
Superhost

Farm stay in Castiglione d'Orcia
4.89 out of 5 average rating, 229 reviewsil poderuccio farmhouse studio apartment
RachelRating, 5 stars3 weeks ago
Great stay! Initially the place was a bit further out of town than we had anticipated but we still found it very accessible to lots of the things we hoped to do! The view was amazing! So peaceful to sit on the terrace!
Guest favourite

Condo in Pienza
4.91 out of 5 average rating, 100 reviewsAmazing view of Val d'Orcia Pienza
IndiaRating, 5 stars1 day ago
Absolutely fantastic! Will be returning!
Top Guest favourite
Loft in Montepulciano
5 out of 5 average rating, 458 reviewsLa Piazzetta - Cozy open space in the historic center of Montepulciano
KatieRating, 5 stars1 day ago
I wish I could give this place 10 stars! After a long day of travel, Guiliano welcomed us into the charming loft with cheese, crackers, Prosecco, cookies, and a bowl filled with ripe fruit. He also stoked the fridge with yogurt, cheese, eggs and a few other items. We made a delicious breakfast the next morning. The loft has the most picturesque postcard view. We just sat and stared often. The bed was extremely comfortable. There were also fresh flowers in small vases throughout the loft. It had so much character. 50 steps away from the front door is the main historic town with all the restaurant and shops. The town is extremely beautiful. This was better than any 5 star hotel. If it is available, Book it now!
Quick stats about holiday rentals in Pienza
Total rentals
60 properties
Nightly prices starting at
$132 NZD before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Marina di Grosseto beach
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Tenuta Le Velette
- Santa Maria della Scala
- Terme Dei Papi
- Cantina Stefanoni
- Basilica of St Francis
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Castiglion del Bosco Winery
- Pubblico Palace
- Golf Club Toscana
- Podere La Marronaia, Sosta alle Colonne
- Cantina de' Ricci
- Cantina Contucci
- Podere Il Cocco
- Madonna del Latte
- Abbey of Monte Oliveto Maggiore
- Poggio Talamonaccio